Humans of Martech

What's up everyone, today we have the pleasure of sitting down with Alex Halliday, Founder and CEO at AirOps.

  • (00:00) - Intro
  • (01:19) - In This Episode
  • (01:54) - Sponsor: Attribution App
  • (02:57) - Sponsor: GrowthLoop
  • (04:19) - How AirOps Pivoted to AI Content Engineering
  • (08:23) - The Real Definition of Content Engineering and Why It's Not About Publishing More
  • (13:14) - What a Content Engineer Does That a Senior Content Marketer Does Not
  • (27:31) - What It Actually Takes to Get AI Content Past a Human Editor
  • (30:52) - Sponsor: Knak
  • (32:00) - Sponsor: MoEngage
  • (43:21) - Why Review Becomes the Bottleneck After You Automate Content Production
  • (47:13) - Why Enterprise CMS Integration Is Harder Than the Content Quality Problem
  • (51:07) - Why the Agent Runtime Is the Next Competitive Battleground for Content Teams
  • (55:02) - What the Case Against Content Engineering Gets Wrong About the Role
  • (58:08) - What a Content Engineering Team Looks Like in 3 Years
  • (01:03:45) - How Alex Decides What Deserves His Energy

Summary: Alex built AirOps to help teams access company data, then a conversation with Sam Altman and a cramped middle seat on a flight to Atlanta changed everything. In this episode, he breaks down what content engineering actually means — not just generating more AI content, but building the systems infrastructure to maintain quality, freshness, and brand accuracy across everything a company has ever put online. He makes the counterintuitive case that great content engineering puts more humans into the content process, and explains why 98% of AirOps's pilots convert to annual customers while most AI content pilots fail. If you think AI content is just a faster way to publish more, this episode will change how you think about it.

About Alex Halliday

Alex Halliday is the Founder and CEO of AirOps, where he leads the development of AI content engineering systems that help brands build visibility in AI search. Before founding AirOps in 2022, he served as Head of Product at MasterClass, where he was the company's first product hire and helped scale revenue 10x. As a Venture Partner at SparkLabs Global Accelerator, Alex has made early investments in OpenAI, Anthropic, Groq, and Discord.

How AirOps Pivoted to AI Content Engineering

In early 2022, the LLM moment hadn't happened yet. Not publicly. GPT-3 existed but was barely on anyone's radar in marketing. Most "AI for marketing" conversations were still about sentiment analysis tools and basic chatbots. The prevailing assumption was that software had rules, rules had limits, and those limits were the floor you designed around.

Alex Halliday had an unusual vantage point. As a venture partner at SparkLabs Global Accelerator with early investments in OpenAI and Anthropic, he was closer to what was actually happening than almost anyone in his world. He still wasn't ready for what came next.

It started with a conversation. He was in San Francisco with Sam Altman, something he made a habit of — whenever they crossed paths, Alex asked the same question: what's sparking your imagination these days? On this particular occasion, Altman's answer was different. The AI stuff was getting really good, he said. When Alex pushed for specifics, Altman told him they were getting close to AI that could read all your emails and tell you what to do for the week. It sounded completely insane.

Alex filed it away. Then, a few weeks later, he was on a flight to Atlanta, sandwiched in the middle seat between 2 large men with nowhere to go and nothing else to do. He finally opened an OpenAI account and started building.

That experience in a cramped middle seat sent AirOps in a new direction. The company had been founded to help non-technical employees access company data — a broad, useful product with no obvious north star. Knowing the paradigm was shifting and knowing what your company should actually do about it are different problems. Alex had to translate that conviction into a focus, which meant making a hard call. When a space is growing as fast as LLM applications were in 2022 and 2023, trying to be everything to everyone is a trap.

The answer came from the data, not from a whiteboard. When the team looked at their heat map of usage, 1 cluster burned hotter than anything else: technical CMOs, leaders of 50 to 100 person marketing orgs, working nights and weekends inside AirOps building ambitious content systems. High-taste users with strong opinions and no patience for tools that couldn't meet their standard. The market was doing what markets do when they find something they want — it was insisting.

By mid-2023, AirOps had committed fully. The customer was the high-taste marketing professional who wanted to build content systems at scale, not just generate more content. Every decision since has been built around that person. The most important pivots rarely happen in planning sessions. They happen when you actually use the thing, look at the data honestly, and trust what the market is telling you over the story you had planned to tell.

Key takeaway: Look at your usage data and find the cluster of users who are working hardest and complaining most specifically — they are telling you who your product is actually for. Make time to try the tools reshaping your industry with your own hands. Alex's pivot started in a cramped middle seat he couldn't escape. Any open hour will do.

The Real Definition of Content Engineering and Why It's Not About Publishing More

Marketing teams have been chasing the wrong metric since LLMs went mainstream. The race defaulted to volume: how many posts, how fast, how much can you automate. That framing made sense in an era where more content meant more crawlable pages, more keywords, more surface area for Google to index. The era has changed.

AI agents now sit between buyers and brands. When someone asks ChatGPT or Perplexity a question about your product category, an agent synthesizes content from across the web — your owned pages, third-party publications, Reddit threads, review platforms — and returns a single answer. That agent is not counting pages. It's evaluating quality, depth, freshness, and what Alex describes as information gain: the degree to which any given piece of content adds something new to what the model already knows.

That's a meaningfully different standard. A 2022 blog post with outdated product language, stale statistics, and broken links doesn't rank lower in AI search — it's absent from it entirely. Webflow, 1 of AirOps's customers, saw what investing in content refresh workflows does to those outcomes: 42% more traffic and AI-attributed conversions performing 6x better than standard organic. That's a maintenance story, not a content production story.

There's also a conflation doing a lot of damage in this conversation. Content written with AI assistance gets lumped together with content generated by AI with no original grounding or context. The studies that say "AI content performs poorly" tend to define AI content as the second category, and the conflation goes unexamined in most LinkedIn commentary. The distinction matters enormously. Content that draws on real interviews, proprietary data, internal expertise, and company-specific context performs differently from content that's a model recombining what already exists on the internet.

The brands performing well in AI search right now are treating their content library as a living system with real quality standards — a garden that requires ongoing maintenance rather than a publishing archive. They're building workflows to keep content fresh, surface internal knowledge that's been sitting in Google Drive unused, and maintain what Alex calls the context layer: the fact base that any automation can run against. That's the infrastructure for AI visibility. More volume built on top of a stale or ungrounded foundation just adds more content that ages out of the picture.

Content engineering, in this framing, is a new discipline that adds the systems layer content marketing never had.

Key takeaway: Before building any new content, audit what you already have for freshness and accuracy. Run your brand name through ChatGPT and Perplexity and note what comes back — what's cited, what's missing, what's wrong. Content not updated in the past 6 to 12 months is significantly less likely to earn AI citations. Start the refresh queue before the production queue.

What a Content Engineer Does That a Senior Content Marketer Does Not

For 15 years, content creation followed roughly the same process: research a topic, brief a writer, check the SERP, publish, and move on. AI tools have changed some of those steps. What they haven't changed, according to Alex, is the fundamental question content teams keep getting wrong: what is the actual job?

The best content has a healthy tension baked in. It has to perform — compete for attention in search results, in AI answers, in social feeds. And it has to tell the brand's story accurately, in the brand's voice, with the brand's actual positioning. Bringing those 2 forces together is the content engineer's job. Pure performance optimization without brand grounding produces generic content that looks like everyone else's. Pure brand storytelling without performance thinking gives you content nobody discovers.

What makes the role distinct from senior content marketing is the internal context piece. Alex is specific about what he means. Sales call transcripts, Zendesk tickets, Loom videos team members created and forgot about, documents sitting in Google Drive that took someone a week to write — all of this is source material that can be turned into demand if it gets out of the firewall and into the world. The content engineer builds the system to do that automatically, and then brings in the right humans to add perspective that only they have.

That framing is worth sitting with. When a product owner gets pinged by an AI workflow to add their perspective on a feature they shipped, they're contributing knowledge that's not available anywhere else on the internet. That's the information gain AI search rewards. The content engineer designs the system that routes those requests to the right people, at the right time, with the right questions, and then builds that knowledge into the content layer.

The talent stack is collapsing in both directions. Engineers are reading through call transcripts to understand customer priorities. Marketers are building workflows, connecting APIs, designing automated pipelines. Alex describes this as leverage, not replacement. People who lived in marketing can now reach into more technical domains to perform their role, and that expanded range is worth something real. Attaching "engineer" to a content role is an umbrella term for getting more done with traditional skills intact, not a career change into Python.

The marketers who understand both what to make and how to build the systems to make it at scale are going to have a growing advantage over those who specialize in only 1 half.

Key takeaway: Map your internal knowledge assets before you design any content workflow. Sales call transcripts, support tickets, expert Loom recordings, product documentation — list what your company knows that nobody else does. That's your content differentiation. Then design your workflow to route that knowledge into your content rather than recycling what's already on the internet.

How Content Engineers Maintain a Library That AI Search Actually Cites

Most marketing teams are in early innings. They've started experimenting with AI for content creation, they've seen what's possible, and then they've realized how much infrastructure actually needs to exist before the creation step matters. Alex calls his internal framework the Fab Five — 5 pillars that ladder up to a full content engineering system. 2 of them stand out as the foundation everything else builds on.

The first is content freshness. Webflow built a workflow with AirOps that periodically reviews their blog posts and looks for positioning updates — product changes, dated references, trend shifts in web design and building. The Pantone colors of the year change. Webflow's product changes. A post from 2022 that was accurate then may be quietly misleading now, and an AI agent reading it won't flag it as outdated — it'll just use it.

The second pillar is the context layer — the fact base that any workflow or agent can run against. Businesses are constantly generating information that should live in this layer but doesn't: a competitor updates pricing, a company wins an award, a product gets repositioned, a new case study closes. Each of those shifts should update the context layer automatically. Without that, the next time an automation runs to update a piece of documentation, it runs against a fact base that's months behind. What goes out reflects a version of the company that no longer exists.

The content engineer owns that layer. Building it, maintaining it, listening for shifts internally and externally, routing the right updates to the right people. That's the job that makes everything else work.

Key takeaway: Build a simple context layer before you build any content automation. Start with a shared Google Drive folder containing your current positioning, key proof points, competitor notes, and recent product updates. Every workflow you build should pull from this folder as a source of truth. Update it whenever something material changes — the quality of your AI content is only as good as the context you feed it.

What It Actually Takes to Get AI Content Past a Human Editor

Anyone who has actually tried to build an AI content system for a brand with real editorial standards has had the same experience: it's harder than it looks. The demos are clean. The first test outputs seem promising. And then you take it to a real editor — or a real CMO — and you discover how much work is still ahead of you.

Alex lived through this from the platform side. When AirOps first launched a basic article template, the workflow had 3 steps. A few months later, he woke up on a Sunday morning to find a customer had built something with more than 100 steps.

Every step in that 100-step workflow was a judgment call someone made over months of iteration: how to pull context, which source to trust, how to format a brief, where to insert a human review checkpoint, how to handle tone drift, what to do when the brand voice slips. The workflow was documentation of everything that professional had learned about getting AI content to production quality. It looked like complexity from the outside. From the inside, it was craft.

AirOps now runs a 3 to 4 week onboarding process for new customers. They audit context, work through tone and voice with the content team, and get alignment on quality standards before any automation runs. It's structured, and it's detailed. Most AI pilots fail because they skip this work — you get the tool running in a day and assume the outputs will sell themselves. They don't. 98% of AirOps's pilots convert to annual customers, and Alex is direct about why: the onboarding process does the real work before anyone has to convince a skeptical editor.

The editors are not the enemy. The system has to meet them where they are. Some editors want to see 4 or 5 briefs and give a 30-second voice memo before the outline is written. Others, once they've built trust, are comfortable reviewing a finished draft. Neither is wrong. The content engineering system has to be flexible enough to accommodate both, and smart enough to learn from their feedback over time. AirOps Next, the platform's most recent release, is built around this: the more a team uses the system, the more it learns their style and incorporates their rules, even from feedback they never articulate explicitly.

Getting to production-acceptable output is a process of building trust incrementally, with the system improving as the team and the tools get used to each other.

Key takeaway: Plan for a 3 to 4 week ramp period before your AI content system produces anything you'd actually publish. Use that time to audit your brand context, align on voice with your editorial team, and build quality checkpoints into the workflow before you hit the review stage. Treating it as a quick setup is the reason most pilots fail.

Where Human Judgment Has the Highest Leverage in AI Content Workflows

Once a content engineering system is running, a new question surfaces: where should humans actually spend their time? Misplacing human effort is 1 of the main ways teams end up with outputs that feel simultaneously expensive and mediocre. Alex identifies 2 areas where human judgment compounds the most.

The first is ideation at the top of funnel. AI can suggest hundreds of content ideas. It can analyze the SERP, identify content gaps, and generate angles by the dozen. But the percentage of those ideas that are genuinely good is low, and high-taste users have a lot of critical feedback when they actually look at AI-generated pitches.

Calling the shots on what gets made, especially for editorial and thought-leadership content, is still very much a human job. The second area is perspective and attribution. AI models do retrieval — they synthesize from what already exists, which means there's a strong bias toward fresh, specific, attributed content. If you can identify who internally has the most relevant expertise on a topic and route the right questions to them, the answer they give you is information that doesn't exist anywhere else on the internet yet. That's the information gain that gets content cited. The content engineer designs the workflow to capture it. The human provides the perspective. The combination is what performs.

Key takeaway: Identify your top subject-matter experts by topic and build intake workflows that route specific questions to them at the brief stage. Even 2 to 3 sentences of attributed perspective from the right person inside your company can separate a piece from the rest of the content competing for the same AI citation. Build the routing, then protect the experts' time by making the ask small and specific.

Why Context Gathering Is 70 Percent of an AI Content Workflow

The most common mistake in building AI content workflows is spending most of the design effort on the generation step. The prompt engineering, the model selection, the output formatting — these are where attention goes, partly because they're visible and partly because they feel like AI. The actual leverage is earlier.

In practice, this means deciding where the right information lives inside and outside the business, setting up the connectors to pull from it, making sure internal content is in a format LLMs can actually use, and structuring the retrieval process so the right subset of knowledge gets attached to the right piece of content. Often the content that exists internally is not ready for use by the models — it needs preparation before the workflow can touch it.

Start with internal sources: a Google Drive folder, Gong transcripts, a shared Notion wiki, whatever the company actually uses to store knowledge. Get that working first, then layer on competitive research. Understanding the ranking landscape for a target query tells you what format is expected, what topics are covered, and where there's a gap worth owning. Competitive intelligence at the query level is a built-in step in most mature workflows.

Then comes the creation process — brief, outline, draft, revisions, feedback, publish — which looks a lot like the old process, but with AI assistance at each step and human review checkpoints built in. Refresh workflows follow the same structure, shorter: a refresh brief specifies exactly what's changing and why, so the editor knows what to look for.

Key takeaway: Before you touch a prompt or choose a model, spend a week mapping your internal knowledge sources. List every place your company's expertise actually lives — call recordings, support tickets, product docs, internal wikis, expert Loom recordings. Set up connectors to the 2 or 3 most valuable ones and get the retrieval working cleanly. The generation step will take care of itself once the context is right.

Why Review Becomes the Bottleneck After You Automate Content Production

There's a pattern that repeats itself when marketing teams successfully implement AI content workflows. The first few months are exhilarating. Output that used to take a week takes a day. Backlogs clear. Capacity feels unlimited. And then, somewhere around the 3 to 6 month mark, things slow down again.

The friction doesn't disappear. It moves.

Alex draws the comparison to software engineering, where AI code generation has created a new bottleneck that wasn't obvious until the code was actually flowing. Review is now the constraint for engineering teams — the work of processing output, evaluating quality, and deciding what actually belongs in the codebase. Content teams are discovering the same thing. You can generate 15 articles in a day that would have taken a month 5 years ago. But reading 15 articles critically, evaluating their accuracy, catching positioning drift, and deciding what's ready to publish is a significant cognitive load. Attention becomes the limiting factor, not production.

That's the risk that doesn't get enough attention. Brands that scale content production with AI and don't invest equally in the review layer end up with a content library that's large and inconsistent — content that talks about the product 7 different ways, uses stale positioning, or presents the brand differently depending on which workflow produced it. The scale advantage becomes a liability when the brand voice frays under the volume.

AirOps built its new platform around this problem. The review surface — how content gets evaluated, adjusted, and approved before it goes out — is as important to them as the generation layer. Making the review experience efficient and engaging enough that people actually do it, rather than rubber-stamping outputs to move on, is 1 of the harder design problems in the space.

The competitive implications run in parallel. When everyone has access to the same tools, volume stops being the moat. What remains is differentiation: experiential content, original research, video, content with genuine information gain that can't be replicated from public sources. The teams that invest in review and quality while scaling production are building the output that still performs when the middle tier of AI-generated content gets commoditized.

Key takeaway: Build your review workflow before you scale your production workflow. Define what good looks like for your brand in writing — specific enough that an AI system can flag when outputs drift from it, and specific enough that a human reviewer knows what to look for. Instrument the review step so it's fast and low-friction. The brands that get this right will compound; the ones that skip it will publish more and perform less.

Why Enterprise CMS Integration Is Harder Than the Content Quality Problem

Building a content engineering system that produces great outputs is 1 problem. Getting those outputs into the places where they actually live — the website, the knowledge base, the partner portal — is a different problem entirely. Most people who haven't tried it underestimate it significantly.

Alex has a line for this: "I'll know we've hit AGI when it can post an article to an enterprise CMS." It's a joke, but barely. He's built the tool side of this long enough to know that Webflow integrations are straightforward. Enterprise CMS integrations are not. There are companies with systems that have a 3 to 6 month lead time on adding a new page — organizations where IT policy governs API access, where structured fields are mapped manually, where a headless CMS schema means a human has to think carefully about where every element of the content goes before automation can touch it.

The AirOps platform is built in 3 layers to handle the full pipeline. The insights layer collects 2 million answers a day from AI search engines, analyzing them for sentiment, citation drivers, and what's moving in a given topic area. The brand context layer stores visual guidelines, positioning, product information, and proof points — versioned and governed, so content automation runs against a current and accurate fact base. The action layer, recently relaunched as agent-first, is what connects those inputs to actual published outputs, including the last-mile CMS step.

For teams that want to run AirOps entirely through their own infrastructure, the platform exposes every piece through an MCP. Ramp, the financial automation company, runs all of their AirOps workflows through an MCP from their own orchestration system. That's an acknowledgment that the top 10 to 15% of users are operating in Claude Code, in their own terminals, and aren't always going to interact through a UI. AirOps has to work in both worlds.

The enterprise CMS problem is a good proxy for the overall operational maturity of a content engineering team. Teams that have solved it have usually built serious infrastructure around their content. The distance between "copy-paste from a text file" and fully automated publishing is a few months of focused work, not a fundamental capability gap.

Key takeaway: Map your content publishing pipeline from generation to live before you build any automation. Identify every manual step that happens between an output being created and it going live on your site. Those are the integration points your workflow needs to eventually handle. Start with the steps that happen most frequently and solve them 1 at a time before assuming the full pipeline can run autonomously.

Why the Agent Runtime Is the Next Competitive Battleground for Content Teams

The conversation around AI operators and the future of SaaS has a tendency to collapse into 2 extreme positions. Either SaaS as we know it is dying because everyone will run agents from the terminal and never log into a UI again, or SaaS will evolve incrementally and the UI stays central. Alex's position is more nuanced than either, and in some ways more interesting.

He agrees the cohort of AI operators is real. People who run their entire AirOps workflow through an MCP in Claude Code, who pay significant API fees and rarely log into a dashboard, who build their own orchestration on top of platform primitives — that group exists and is growing fast. But content is also a team sport. It involves editors, CMOs, legal reviewers, subject-matter experts. Most of those people are not working from a terminal. The review friction that teams are now discovering as their main bottleneck is not a problem that a CLI experience solves well.

What's emerging as the real question is where agents run — and the answer has real consequences. Cloud agent runtime versus local machine-based agents has meaningful differences: cost structures, observability, multi-party human-in-the-loop capabilities, how agents improve over time, and what data they can access. AirOps has been working closely with Anthropic on this and is making a specific bet: a purpose-built cloud agent runtime for content engineering use cases will outperform a generic 1. The fact base, the brand context layer, the 2 million daily answers from AI search engines — these are data assets that a specialized runtime can incorporate in ways a general-purpose runtime cannot.

There's also a governance problem surfacing among CMOs. When content is being generated by multiple workflows, some in-house and some via platform, and the brand context isn't governed, you get content that describes the product 7 different ways. Purpose-built SaaS with a structured, versioned brand context layer is positioned to solve this better than a collection of API calls assembled from scratch.

SaaS built for AI operators — with the infrastructure and observability that enterprise content teams actually need underneath the automation — is where this is heading. The teams thinking about agent runtime now will have a structural advantage when the rest of the market catches up.

Key takeaway: Set up a governed brand context source of truth before scaling any content automation — a versioned, shared document that defines your positioning, product facts, tone guidelines, and current proof points. Every workflow you build should pull from it. When the positioning changes, update it once and every downstream automation updates with it. That's the governance layer most teams are missing, and the 1 that will matter most as agent runtimes mature.

What the Case Against Content Engineering Gets Wrong About the Role

There's a credible critique of content engineering making the rounds. Ryan Law at Ahrefs published a piece called "I Wouldn't Hire a Content Engineer," arguing that the role is hiring for skills that won't be needed long, and that a great writer with no AI fluency beats a middling writer who knows all the agentic tools. It's a position worth engaging with directly.

Alex hasn't read the specific piece, but he's read the genre — critiques that treat content engineering as automation-for-its-own-sake, as if the goal were to reduce writer involvement. His actual belief about great writers is that they're invaluable and should be protected. The whole point of content engineering is to create conditions where great writers can do their most impactful work, instead of spending their hours on the parts of the job that automation handles better. A great writer who goes into a session prepped — knowing which questions they should be answering, having done the competitive research, having context on the current discourse — produces something different from a great writer starting from a blank page.

The deeper issue is what happens to the content library when the best writers are focused only on their best work. There's a lot of area under the curve that doesn't get covered. Existing content ages out. Documentation goes stale. The long tail of questions buyers are asking never gets answered. That unaddressed surface area is a marketing liability — content decaying in place while the writers work on the flagship pieces. Content engineering is the system that addresses the library, not the system that replaces the people writing the flagship pieces.

The skills question is also worth addressing directly. The most effective people in every knowledge work discipline right now are adding some systems and technical fluency to what they already do. The mind of an experienced writer has genuinely creative ways to use these tools that a non-writer probably wouldn't think of — the brand instincts, the judgment about what's worth saying, the feel for what will actually resonate. Those skills compound when combined with the technical layer. The right answer is pairing, not replacing: great writers doing the work that requires their judgment, with content engineering systems handling the infrastructure around them.

Key takeaway: Evaluate your content team's current workflow and identify which tasks require real editorial judgment and which are logistical. Research, brief writing, competitor analysis, content inventory management, refresh tracking — these are strong candidates for automation. Reserve editorial decision-making, top-of-funnel ideation, and point-of-view development for humans. The split changes the output quality of both.

What a Content Engineering Team Looks Like in 3 Years

Forecasting 3 years in this space feels like guesswork. But Alex's prediction is grounded in what's technically possible now, not in speculation about breakthroughs that haven't happened yet.

His view: marketing teams will onboard a new subteam within the next few years, and that subteam will be captained by a primary agent with a team of specialized subagents underneath it. AirOps is building that team for the content engineering and content operations use case. The human members will be there to react, exercise taste, contribute perspective, and make calls that require judgment — not to handle the logistical work the agent layer manages.

The working session he describes: a few highly productive hours inside the platform where you arrive and find a set of prompts ready for you. Some ask for your opinion on a positioning call. Some flag a shift in what competitors are doing in a particular topic area. Some surface a content gap that opened since last week. You exercise taste, add a voice note, approve or redirect. The agent layer does the rest.

The goal is to make that experience genuinely engaging — because when it's engaging, more people inside the company want to participate. Product owners contribute perspective. Customer success shares anecdotes. Customers contribute their own points of view. The content footprint becomes a collaborative, living thing with energy and distributed ownership behind it, rather than a burden carried by a small team.

What changes in 3 years is the degree to which these systems are proactive. Most content engineering today is reactive — teams build workflows that respond to prompts and assignments. The next phase will produce systems that surface the right opportunities before anyone has to ask for them. Trust increases as context and capabilities increase, and the coverage gap between what teams could theoretically do and what they're actually doing starts to close.

Key takeaway: Pilot a regular content intelligence session with your team now, even if it's manual. Spend 1 hour per week reviewing: what content is being cited in AI answers, what competitor content is ranking, what customer questions are going unanswered, what owned content is going stale. Build the habit before you automate it. The teams that already have this operating rhythm will adapt to the agent layer much faster when it arrives.

How to Stay Current When the Tools Shift Every Few Months

Knowing how to use the tools that exist right now is only part of the challenge. The tools are changing fast enough that what works in 2026 may not work the same way in 2027. That creates a real question for anyone trying to build a durable skill set in content engineering: what's worth learning, and how do you stay current without going in circles?

Alex's answer is less about specific tools and more about the practice of experimentation. Doom scrolling industry commentary about which model is best or which workflow is now deprecated feels like learning and produces anxiety. What's actually productive is treating experimentation as a professional duty, the way other disciplines treat staying current with their field.

AirOps has institutionalized this internally with "play" as a core operating principle. Not building sandcastles — following curiosity, trying things, and sharing what works. Alex spends roughly 1 full weekend day per week building inside the platform, following whatever thread his curiosity is pulling on. That time gives him energy, feeds his thinking, and keeps him current in a way that reading about the tools never would.

The gap between the top marketers and the median marketer is wider now than it's ever been. It's not a gap in intelligence or even experience — it's a gap in hands-on experimentation. The people at the top are building things, trying things, accumulating reps. Reps are how you stay current when the tools shift, because you develop the pattern recognition to learn new tools faster, to evaluate what matters, and to make judgment calls that no course or tutorial can teach. The specific skills matter less than the practice of building them.

Key takeaway: Carve out 1 dedicated hour per week to experiment with a tool or technique you've been curious about but haven't tried. Set a specific question to answer with it — something connected to your actual work. Document what you learn. After 4 weeks, share it with someone on your team. The experimenting is the training.

How Alex Decides What Deserves His Energy

Most people who run a startup discover at some point that the job is designed to consume everything. The decisions don't stop, the priorities compete, and the weeks blur together in ways that are hard to account for. Alex has built a few intentional structures around this.

The first is a personal Claude whose job is prioritization. As the business has grown significantly, having a system that's been given context about his goals, his time constraints, and where he tends to get pulled off course has become a genuine tool for staying on track.

He splits his week into 2 explicit categories: need-to-dos and things that give him energy. The energy-giving category gets protected time — specifically, 1 full weekend day per week spent building inside AirOps, following whatever he's genuinely curious about. That time has a dual function: it keeps him close to the product and it gives him something that isn't transactional. Following curiosity in a creative, low-stakes environment is how he recovers enough to do the high-stakes work well.

The physical and community side is harder to be consistent about, and he's honest about it. There have been periods where he's neglected it, and he's direct about what that cost him. Running a startup takes a sustained toll in ways that are easy to underestimate until you're already in deficit. This year he's being more intentional about it — getting outside when the weather allows, treating wellness as part of the job rather than a reward for finishing it. The West Side Highway in New York just reopened as the weather improved, which helps more than it probably should. The Claude yells at him when he skips his things. The balancing act continues.

Key takeaway: Identify the 1 or 2 activities in your work week that consistently give you energy rather than drain it. Block time for those the same way you block for meetings. Then identify what tends to consume your attention without proportional results, and get something — a system, a person, a Claude — to help you push back on it. Energy management is the meta-skill that makes every other skill more sustainable.

Episode Recap

Alex Halliday's central argument is one the industry keeps misreading: content engineering is a discipline that puts more humans into the content process, not fewer. The goal of the content engineer is to find the right people inside an organization, route them the right questions, and build their knowledge into a content system that can maintain and scale it — rather than replacing human judgment with automated output that recycles what already exists on the internet. The brands performing well in AI search have figured this out. The ones generating volume without that infrastructure are quietly building a liability.

The tactical thread running through the episode is the systems layer that content marketing has never had. A content library treated as a publishing archive decays in place — posts go stale, positioning drifts, the fact base running underneath any automation falls behind the business. The teams winning in AI search have built context layers, refresh workflows, and integration pipelines that treat their content library as a living asset. AirOps's work with Webflow — 42% more traffic and 6x better AI-attributed conversions from refresh, not new production — is the clearest illustration of what that investment actually returns.

The conversation also surfaced something that doesn't get enough attention: the friction doesn't disappear when you automate content production. It moves. Review becomes the bottleneck. The attention of the people doing the review becomes the limiting factor. Brands that scale production without equally scaling their review layer end up with large, inconsistent content libraries that dilute their brand voice at scale. Building the review infrastructure is as important as building the generation infrastructure, and in Alex's experience, it's the part teams consistently underinvest in.

There are honest tensions in the episode worth noting. The question of where agents should run — cloud runtimes versus local machines, SaaS platforms versus API-first operator setups — is genuinely unresolved, and Alex is direct that it's an existential question for companies like AirOps. The enterprise CMS integration problem remains hard in ways that are difficult to automate around. And the skills question — what junior content marketers should build toward, whether content engineering is a durable role or a transition role — doesn't have a clean answer. Alex's bet is that the blend of traditional writing craft and systems fluency will compound over time, but the ratio is still being worked out in the market.

You can follow Alex on LinkedIn and learn more about AirOps at their website.

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[00:00:00] Phil: What's your take on how content engineering helps teams that don't want to just build more content at scale, but instead want to write things that can't be replicated from public data?

[00:00:09] Alex: when we think about the construction of like a content system or the content engineer. a lot of that context is collected and, gathered automatically, but then because on a call transcript, someone has started asking about a new regulation or a competitor feature, who internally is the right human to then go and get an updated response or to an updated positioning on that.

[00:00:29] And so the goal of the engineer is not to remove humans out of the loop. It's actually to find more humans to put into the loop, but but have them practice at the top of their license. So we spend a lot of time thinking about what unique context exists inside the business and what humans that we can leverage to get more knowledge out into the world, that is a systems problem. That's a human problem, that's a strategy and taste problem.

[00:00:52] ​

[00:01:19] In This Episode
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[00:01:19] Phil: What's up everyone? Today we have the pleasure of sitting down with Alex Halladay, founder and CEO of Air Ops. In this conversation, we cover what led to Air Ops pivoting to AI content engineering, what a content engineer does that a senior marketer doesn't, and what a marketing team looks like in three years.

[00:01:35] We'll also talk about what it actually takes to get AI content past a human editor and why enterprise CMS integration is harder than the content quality problem. To make the most of this conversation, joining me as co-host today is the Mad marketing scientists and my dear friend and firm, our co-host John Taylor.

[00:01:52] We'll dive in after a quick word from two for awesome partners.

[00:01:54] Sponsor: Attribution App
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[00:01:54] ​

[00:02:57] Sponsor: GrowthLoop
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[00:04:00] Phil: Alex, thank you so much for your time today, sir.

[00:04:02] We're really excited to chat.

[00:04:04] Alex: guys, such a pleasure to be here. Excited to dive in.

[00:04:07] Phil: So a lot of folks are probably familiar with, uh, AOPs. We are excited to get the founder on the show and, uh, you know, be remiss by not getting a chance to at least chat about some of the founding story. Uh, the history behind the company.

[00:04:19] 1 — How AirOps Pivoted to AI Content Engineering
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[00:04:19] Phil: You started AOPs in 2022. Uh, the initial product was to help non-technical employees access company data.

[00:04:26] And you quickly saw that a lot of the marketers that were in your user base were showing up and a lot of them were taking that data and feeding it into content workflows. And in parallel to this, you were an early investor in open AI and philanthropic, and so you kinda had this like inside track on the crazy capability curve of, of LLMs.

[00:04:45] Talk to us about, like, at some point why AOPs became a content engineering platform for AI search. Like when did the turn actually happen? Uh, what did you see that kind of made you commit to it?

[00:04:56] Alex: Yeah, for sure. I mean, I think as you pointed out, AOPs was formed [00:05:00] pre LM so we, we were building for six months to a year before I had even touched the kind of early LMS from OpenAI. And I remember, um, I was actually, uh, having a conversation with, um, of all people, Sam Walman in San Francisco, and this was like early 2022.

[00:05:18] And I ask him the same question every time I see him, which is something along the lines of, what's getting you really excited these days? Or kind of what's, what's like, what's sparking your imagination? And he just looked at me and he said, the AI stuff's getting really good. And I, and I sort of dug in. I was like, what use case are you excited about?

[00:05:34] Like, what, what do you mean? Because up until that point, we didn't really have general purpose AI in the way that we do today, obviously. And so he, he said to me, you know, we're getting close to the ai, being able to read all of your emails and tell you what, what to do for that week, which sounded back then totally insane to me.

[00:05:51] Um, and, and I planted in the back of my head at that point, this idea that I should go play with the models and figure out what was happening, OpenAI and create an [00:06:00] account. Um, and then on a flight to Atlanta. I decided when I was sandwiched between these two gigantic gentlemen and I was in the middle seat, I was like, how am I gonna use this time?

[00:06:11] I was like, okay, I'm gonna now go and finally play with this OpenAI thing. So I signed up and create an account and uh, I remember just having, just almost now body experience as it started to generate perfect sequel and create copy and do all these insane things that really, for me started to melt the laws of physics that had governed software for the last 20 years.

[00:06:32] And I, I like obviously had no idea of how this was gonna unfold, except that I felt very clearly this was like a massive paradigm shift and AOPs should figure out how it should be part of our story. So we started experimenting in that direction and initially the product was very broad, but when a space is growing as quickly as, as the kind of LLM application space is, I felt very clearly that it was important to pick and own a focus slice of that universe and not try to be [00:07:00] everything to everyone.

[00:07:01] Um, and when we looked at the kind of heat map of usage and the kinds of people that were getting value from us, it, there was this bright white heart kind of center of activity with people working nights and weekends and building crazy ambitious things. And it would these technical CMOs, like CMOs of 50 to a hundred person marketing orgs that were diving in and building with AOPs.

[00:07:25] And it was just one of those moments where you saw the market telling you, Hey, we like what you're doing, and we as a high taste user have really strong opinions on what we want to do with this technology. Um, and, and at the point we lent into that, it took a little while to make that decision, but we lent into that and never looked back and have just loved building for this customer ever since.

[00:07:47] And that was probably around the beginning of, of 2020, um, mid, mid 20, 23, 24, that that really happened. And since then, that's been our sole focus, who we talked to every day and who we build for.[00:08:00]

[00:08:00] Phil: Super cool. I feel like everyone has that like moment in history now. Like the first time they spun up Che GVT and asked their first question and started getting a taste of the potential here. And it's crazy that we're we're only just, uh, you know, less than half a decade away from, uh, when GPT-3 launched to, to the public.

[00:08:18] And now some of the crazy stuff we were just chatting about before we press record. Um,

[00:08:23] 2 — The Real Definition of Content Engineering and Why It's Not About Publishing More
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[00:08:23] Phil: but I, I do wanna like get, let you introduce or maybe get your definition of like what content engineering is like. We, a lot of our listeners are in marketing and, and play around in the marketing sphere. We are familiar with like marketing, engineering, GTM, engineering and like content engineer.

[00:08:41] Um. Marketing seems to always have a need to create new terms in an attempt to kinda like redefine our jobs. But content engineering is interesting because as a term it's existed for a decade. It, it comes, uh, it comes out of like technical documentation world. If you feel like on LinkedIn there's like thousands of people with like technical content engineering [00:09:00] roles.

[00:09:00] Um, but you've kind of taken this framing and applied it to something that is way newer than than the old school way of thinking about this. So you're building operating AI content systems at scale specifically to optimize AI visibility. A lot of people start having a negative connotation when they hear content systems and AI powered content 'cause they immediately think of the generic sloppy content that looks the same everywhere that we see on LinkedIn across social.

[00:09:28] What's your take on how content engineering helps teams that don't want to just build more content at scale, but instead want to scale specificity and write things that can't be replicated from public data?

[00:09:41] Alex: Yeah, I think it's a, it's a really interesting, um, question and I think if we zoom out and look at what's happening at the moment, there is now, um, new priority audience for marketing and content teams. Which are these AI agents that act as an intermediary between [00:10:00] buyers and brands. And one of the behaviors of these AI agents is they're able to synthesize large amounts of content, form a consensus, and then, and then give a single response in a very efficient, um, you know, single pane of glass back to a user.

[00:10:15] And when we look at that system, um, we start to see that the quality, depth, freshness, and information gain of all of this content really matters. And so you wanna make sure as a brand and as a business that the content that you have on your own website, the content that you publish to partners, how you show up in Reddit, how you show up on third party sites is as on messages as ac and as accurate and as, um, good at preempting real customer questions as possible.

[00:10:42] And so, in our view, this is a big challenge, um, and one that, uh, you can't simply throw more people at to try and meet, meet this need, I think for a long time. Um, content was seen as being kind of an incremental, um, you know, we want to publish x [00:11:00] blog posts a month, or we wanna refresh YY post a month. In this day and age where the models are reaching into the long tail, increasingly pulling a lot of content, um, and, and synthesizing answers, the need to keep content fresh and accurate, um, is, is really needs a systems response, not just a human response.

[00:11:20] But when we think about AI content in general, there's this like, kind, it's kind of slight of hand, and you'll see it over LinkedIn all the time where the headline, and actually one of our competitors has been publishing nonstop on this topic. The headline is always AI content. Um, is leading to bad outcomes for brands.

[00:11:38] And then you click on the study and you scroll down and it says solely the definition then changes to content, which is solely generated by AI with no original grounding or context. And I think that that conflation is very dangerous, um, because the details matter. The reason it takes us three to four weeks to onboard a [00:12:00] customer is because we spend a lot of time thinking about what unique context exists inside the business and what humans exist inside the business that we can leverage to get more knowledge out into the world, but can then be rewarded with visibility.

[00:12:13] And that is a systems problem. That's a human problem, that's a strategy and taste problem. Um, and so when we think about who's successful in this era, it's typically we're seeing more and more it's these high taste professionals that can augment themselves with a few technical skills to take advantage of the AI in precise ways.

[00:12:34] Build systems think creatively about applying these technologies. And that's why we've kind of lent into this term content engineer because it's taking all of the best things that content and mar content marketers and marketers have, have been doing, um, telling their brand story, but, but augmenting it with a few additional skills to allow them to meet this moment and be successful.

[00:12:55] But, but the, the, the distinctions here between, you know, mass produced [00:13:00] ungrounded content that was really prevalent in the first act, this and what's happening in sophisticated brands that deeply care about their brand heritage now is like night and day and actually very misunderstood, I think by a lot of people.

[00:13:14] 3 — What a Content Engineer Does That a Senior Content Marketer Does Not
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[00:13:14] Jon: One of the things that I, and I want to just dive a little deeper here and maybe make sure that I've, I fully understand your definition and that we're on, like kind of operating off the same page, but like, I love the idea of the engineer, right? Like I've thought of myself as a marketing engineer, et cetera, in the past as well.

[00:13:29] But what I think you are kind of laying out here is this idea that content is, is an equation to some extent or another. I've been a writer for 15 years. Honestly, the way I assemble content 15 years ago is more or less the same way. Research it, brief it, check out what the competitors are saying. But now with AI tools, there's this entirely different layer where you can automate all the, the inputs, right?

[00:13:52] Like the basic inputs as they come in. It sounds like what you guys are doing are working with the brands to bring in. Their personalized [00:14:00] context, right? Like the, I don't know if you guys handled sales transcripts, but as a, as an SEO guy, I would take sales transcripts over a keyword data sheet 10 times outta 10.

[00:14:09] I think, uh, I'm curious if, if you start to see the engineer's role in this as being really twofold. Fold one or part one is arranging the data, sets the inputs, making sure that everything's tuned in the system. And then the other side is turning out what the output is, the quality of the output, the direction of it.

[00:14:28] Like content isn't just a blog, it's a landing page, it's a podcast, it's a LinkedIn post. Is that a rate framing from your perspective? And, and, uh, what would you add to that?

[00:14:38] Alex: I think the, the, that the best content has a healthy tension. Um, because ultimately content is operating in a co in a competitive market, you're, you're competing for attention in the SERP in chat, GT's response in TikTok. So there is an element of the co an element of creating content where what's gonna perform well needs to be a voice in, [00:15:00] in the output.

[00:15:00] Otherwise, you know, you're creating things that don't, that doesn't resonate, doesn't perform. And then the other is the brand voice as well and the, the brand story, the positioning, the things the brand wants to say to the world. Um, and so, so when we think about the role of the content engineer they're actually bringing together, um, and, and trying to meet those, those tensions with content that both performs well and is on brand and continues to tell the story of that brand and the ingredients to that are as obviously kind of AI as a part of that.

[00:15:30] But also as you mentioned that the internal context, which is so often misunderstood, so cool. Transcripts are amazing. Zendesk tickets are amazing. Loom videos the team are creating are amazing things that are sitting inside of Google Drive, collecting dust that someone spent a lot of time on. All of this context internally can be, can can lead to new demand eyeballs if it can be safely gotten outside of the company's firewall into the web.

[00:15:55] So those pieces are really important. But then I think when we think about the construction of like a [00:16:00] content system or the content engineer. Um, a lot of that context is collected and, and gathered automatically, but then when we're answering a specific question, um, because on a call transcript, someone has started asking about a new regulation or a competitor feature, who internally is the right human to then go and get an updated response or to an updated positioning on that.

[00:16:22] And so the, the, the, the goal of the engineer is not to remove humans out of the loop. It's actually to find more humans to put into the loop, but but have them practice at the top of their license. So if I get pinged as the product owner of a feature I shipped by, by AOPs or another platform to, to contribute to a piece of content that then allows that piece of content to be more successful when it goes out into, into the web.

[00:16:45] And so the idea that the goal is to have completely autonomous systems that just run is actually not, I don't think it works. And I actually think it misses the point of what can be achieved when you are partitioning. A lot of the, the, the automatable pieces off of the human's [00:17:00] plate and focusing them on net new opinion reactions, additional context that lives inside their head.

[00:17:07] Phil: Very cool. Alex, can you help us like paint a picture of what this new body of tasks looks like inside some of your customers that are coining some of these new roles, like content engineers, um, like are they mapping out like fan out queries for content and like making sure that the pipelines are pulling from the CMS and a refreshing process, like loading brand context, like there's a bunch of stuff in this like system in the pipeline.

[00:17:35] There's a whole measurement layer also, like walk us through some of the, the roles. Paint that picture for us.

[00:17:41] Alex: Yeah, I think. We, we, we talk about it internally as the Fab Five, um, because there's kind of four, five core pillars. I won't talk about all of them now. We'll be here for a while. But I think a couple that really stand out is one, thinking about content freshness. Um, so if you have spent the last five years as a business building a [00:18:00] fantastic blog, your web flow is one of our customers, for example, and they have this fantastic blog that's been a labor of love for the last few years.

[00:18:08] A lot of those posts age periodically, either because the web flow product shifts, or because the content comes out of date. Um, 'cause trends shift a lot in web design and building. And so one of the things we have, uh, they've built with us is, um, a kind of workflow that periodically reviews their blog posts and looks for positioning updates in their product that they want to go and update or, um, things that have become dated.

[00:18:35] So, for example, the web, uh, like web, um, Pantone colors of the year or kind of web colors of the year. And those trends shift. And so they're able to use Arop to keep those updated. So the mindset shift of content is published and done. Um, on the one hand to content is an ongoing gardening maintenance opportunity and actually a really big growth lever given how much.

[00:18:55] AI models in particular, love, fresh content is an important one, and that the [00:19:00] systems to power that are very, very important. And then another one I would, I would add is, um, is thinking about the maintenance of your core, like context layer. So when we think about the context layer, it's kind of the, the, the fact based that any automation agent or workflow can run off of.

[00:19:16] And a lot of things happen in a business and outside of a business that affect that context layer. So for example, you know, um, a competitor launches, uh, updated pricing and we need to have a competitive response to that stored somewhere in the context layer. Or the business, uh, has some fantastic new proof points or wins an award that all of the listening to that shift internally and externally and maintaining, um, that context base, um, is something that the, the, in our view, the content engineer can own to make sure that when an automation runs to update documentation, for example, it underst.

[00:19:52] The present state of the business and that the product, um, and you can have, you can make sure what you're putting out there is, is grounded in a [00:20:00] really, really strong fact base. So the, the, the sort of five pillars ladder up to an entire system. And to be honest, most, most companies are still in the early innings of, of layering those on.

[00:20:10] But, um, the goal is to have, uh, kind of just increased impact of the same set of people within, within the, within the marketing org. Um, leveraging AI in the places it's really good and pushing to humans and the places where we, we need them to, to contribute.

[00:20:27] Jon: It is super, super smart approach to to all of this. I think one thing that jumps out at me is this role of the engineer is also about the scale. The scale of things, right? Like as an individual, SEO, years and years ago, maintaining something as simple as internal links. Like we redesigned the homepage and now we've got new top nav links, and guess what?

[00:20:45] You've got 10,000 pages on a site. Good luck finding these 50,000 links. It sounds like you guys are starting to solve that with having workflows in place and listening in place, and the context to be able to say, oh, big brand shift. Now we're going into [00:21:00] market.

[00:21:01] Alex: I, I, I think there's, or one of the problems with the AI conversation and just something I wanna call out is that, um, you know, a lot of the content is around making people feel like they're behind. You know, like LinkedIn is full of, like, I, these five prompts have changed, changed our company trajectory here.

[00:21:17] I, I think that's, that works really well on social. It's designed to kind of trigger an emotion. Obviously the, the, the really important message here is that everybody is at some point on this journey, and most

[00:21:27] people are relatively early and starting to build their first automation. And so I don't want like people listening to this to feel like, oh my God, I'm so behind and everything's ed, and what am I gonna do?

[00:21:38] Th this is really a, in. Fabulously creative moment in, in this industry. And everybody needs to sort of chip away at that with just building their first thing, getting their hands dirty, using, going, we, we have a wonderful free training program. People can get their hands dirty in Claude code, but just get your fingers on the keyboard and start building things.

[00:21:56] And, um, it's, it's a, it's a, it's a big spectrum of [00:22:00] adoption and everybody is at one point on that

[00:22:03] Jon: Yeah, thank you for saying that. It needs to be said at least once during the podcast, and I appreciate taking a little bit of the, the air to that balloon. It's making LinkedIn insufferable for, for practitioners like myself,

[00:22:13] like, uh, it, now what I love about, about this conversation is how pragmatic it is, right?

[00:22:19] Is, is these things are not novel things, right? The activity, the deliverable, refreshing content, this is, you talk to any SEO worth or salt, they'll tell you, I'll put $10 on this before I put it on new content 'cause it's so valuable. Now there's also the LLM angle to this, and I want to get your, your take on this as well is like within your own system and the learnings that you and your customers have had, like the LLMs will often cite that old content as well.

[00:22:45] Do you find that these are the types of positioning opportunities that aren't just like, we'll boost some SEO, we'll make sure positioning's good, but we're also feeding the LLMs really valuable information and that adding like an extra spark to the fire, uh, behind adoption of your own product.[00:23:00]

[00:23:00] Alex: Yeah, I think we, we, um, increasingly, I'm actually very interested in this. I think the idea that, um, the first wave of SEO and, sorry, a EO conversation was about, we mentioned in the result, and now I

[00:23:12] think the conversation is shifting a little bit to what is the opinion the model is forming? What is the kind of consensus opinion do people think we have?

[00:23:21] Well, for AOPs, for example, you know, people may ha think our pricing is complicated. Okay. Which is, which is a very real thing. Um, and so me as a, me as a ao uh, platform, um, you know, I'm concerned about that opinion. I wanna understand why do people think that? And, um, actually being able to drill into the source conversation, be that a read, a conversation, a blog post, a sta, a stack overflow that someone wrote, um, allows me to go and then outreach to those people and, and address the core concern and, and shift that opinion.

[00:23:51] So LMS present a lot of the similar challenges of building authority, having deep content, but they also slightly change. I'd say the [00:24:00] contrast on some of these things to make something slightly more important. And this idea of model sentiment and the fact base and the opinion it forms for specific personas, for specific points in the buying journey is kind of a new frontier for us.

[00:24:12] So we are shipping a lot to support those kinds of, um, uh, remediatory like workflows and agents that can help with those specific things. But it is a, it's a very important actor in the buyer journey now to influence.

[00:24:26] Jon: It is funny how, how the market has shifted a little bit from last year of I gotta be cited at all costs to now I'm seeing a much more, it, it are the LLMs accurate. Like I think there's a recognition that these LLMs hallucinate all the time. I built like my own internal LLM visibility tracking tool and like the amount of hallucinated URLs that you find in the content, uh, from brands you own and and so on is, is actually really.

[00:24:53] It's, it's actually good news for people who think they're behind or like, wait, these LMS are great. Uh, but they're not infallible.[00:25:00]

[00:25:00] Alex: Yep. And I think if you look at the average length of a question in chat GBT, and you add on things like personal intelligence from Google, you add on the increased context that CHATT has about you in its memory, you know, what's you're seeing is these models are going more and more into the long tail to find kind of novel tidbits and things, and that's dredging up a lot of really

[00:25:21] old content or content that's inaccurate.

[00:25:24] Um, and so, um, the, that, that kind of long tail challenge is, is very real for brands and something we, we talk a lot about, but it does mean that you can end up with totally wild responses from stale opinion or things that reflect your product or service from, from two years ago. So it, it's, it's very, it's in so many ways we're, we're moving really fast and in so many ways.

[00:25:46] We're still very early in a lot of

[00:25:48] these things.

[00:25:49] Jon: I. it last one of them, Phil, I'll, I'll shut up for a second and give you a chance, but one of the things, again, coming back to this engineering perspective, like engineering has been typically reserved for people who build [00:26:00] products. But largely what I'm seeing from the, your framing is your content's a product and if you have vulnerabilities in the back end of your product, you know, it doesn't matter if you coded it 10 years ago or yesterday, it's still a vulnerability.

[00:26:12] And I feel like that's the G gap your company's closing.

[00:26:17] Alex: I am really. Excited about this kind of collapsing of the talent stack, meaning that the same person who lived in marketing can now reach into more technical domains to perform their role and vice versa, right? We have engineers who are now. You know, looking through cool transcripts with our customers and prioritizing features, it's a very exciting time for the willing and the curious.

[00:26:38] And so attaching engineer to a content role doesn't mean we expect people to be to learn Python, but it means that in now they're, people are, um, able to go and be far more, um, impactful and, and can scale their impact as a professional and actually have a path as the world changes pretty quickly. So if we, if we can flip as air ops, if we can flip [00:27:00] people to feeling a little bit behind, to feeling like they're participating in this shift and they get some new skills and they get, they get some confidence and excitement from this and that allows them to expand their agency or their business, I think we've done our job and that makes me feel really good about our role.

[00:27:15] So the content engineering thing, I think is, is a, is an umbrella term for people getting more leverage in this moment, but still bringing a lot of their traditional skills, their taste and their strategic thinking to, to this challenge as it shifts.

[00:27:31] 4 — What It Actually Takes to Get AI Content Past a Human Editor
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[00:27:31] Phil: Alex, I wanna give you a chance to chat about how Air Ops is helping some of the hurdles related to content engineering. Like when I chat about this to folks, a lot of folks think that content engineering sounds really easy and straightforward, but anyone that has done it, like I don't have the, the year plus experience that, uh, John does, but I've been like automating a lot of the.

[00:27:52] Post-production pipeline on the podcast in the last few months. And, you know, getting past that, like, human editor, for me, that's [00:28:00] like myself. But in a lot of cases you're working with a content team and it's really hard. Like, that's like the, the final boss is like the, the human editor here. Um, the value of like institutional knowledge, that context layer that we talked about, it's a tall order to solve with a workflow and maybe you like chat about like, working with your customers.

[00:28:19] What are you seeing in terms of like how to cross those hurdles? Are we ever gonna attain this like, production acceptable output? Should we kind of accept that the goals, the goalposts are always kind of changing and this is more of like a dynamic thing? What are your thoughts there, Alex?

[00:28:34] Alex: Yeah, I mean I think that when we, it was really funny when we started at AOPs and we, we had our first. Kind of create an article template. And I think it was like three steps in the workflow. It was like

[00:28:44] very early, we didn't know anything, right? We were like, oh, let's just see how people use it. And then I woke up on a Sunday morning and we had workflows that were a hundred plus steps.

[00:28:52] And it was one of those moments where it's like the difference between an output and an outcome was just so starkly illustrated on this [00:29:00] canvas. And I think in that is all of the, like, the learnings, the taste, the kind of nuance, the things that this professional who's building on our platform had accumulated over the years about how they want to work, how they want their brand to sound, and the kinds of things you actually need to do to get, to get really good, um, outputs from an LLM.

[00:29:18] And so, um, I think that the, the, the kind of. The, the, the interesting thing is decomposing the pipeline that you have today and thinking about which things are great candidates for ai, which things may have been impossible before that you can now go do. So trolling through historic transcripts, for example, to look for references you may want to include.

[00:29:39] Um, and then, and then really keeping humans very front and center until you can get a little bit more confidence in some of those things to hand them off. So it is a labor of love that I completely. Miss, uh, did not appreciate at the beginning of this journey, but have, but building against high taste brands and people that really, genuinely care is the best way to get good at something because as you [00:30:00] are, as you alluded to, like, people will not put things on their website that they are not happy with and they certainly won't, uh, pay for a platform like AOPs.

[00:30:08] So most AI pilots fail, but 98% of our pilots convert to, to people becoming annual customers with us, who work with our team. And that's because the three to four week process, we put people through the sort of content engineering boot up where we like audit their context, we help 'em think about their tone and voice.

[00:30:26] We get them to agree how they wanna speak, um, is is very structured. It's a lot of detail in there. And the only way we were able to do that was by, um, running into the fire for the first year and learning all these things. So again, like it's, it's, it's so easy to do things with AI that gets conflated with actual business outcomes and the two things which is wildly different.

[00:30:46] And in that. In that space is the craft of content engineering and, and content marketing.

[00:30:52] Sponsor: Knak
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[00:32:00] Sponsor: MoEngage
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[00:32:57] Jon: O one of the things that I've broke my back on a few times, [00:33:00] it sounds like you guys have solved, so ku kudos to you. But like whenever I've tried to build these automation content systems very similar, I've arrived at the uh, uh, the conclusion of multiple workflow steps are required. Clean up the data, put the brief together, get research, all that fun stuff. How do you end up designing a system that isn't defensive against the editor? Like the editor is, is gonna end up, for most brands, gonna be the, the main stumbling block, at least in my experience, especially if the editor has any bias towards AI assisted content. Uh, and, and we immediately see, okay, if they think it's AI assisted, they'll put a different complete level of he, uh, uh, heuristics and, and criticism against it.

[00:33:40] And so I've fallen into the trap in the past of building very defensive systems that ended up sitting on good amounts of data. It's just like your clients are of all these transcripts and stuff like that, and it comes out so vanilla and the only way I could solve it. I'm curious if this is like just baked into your platform as a workflow step, is that human element that 20 seconds on [00:34:00] whisper flow where I, Hey, this is what we're actually trying to achieve here.

[00:34:03] Like, is, is that the right way to think about this? Is that how you guys solve the problem or,

[00:34:07] yeah.

[00:34:08] Alex: I, I think our view is that we should have as much, the starting point should always be as much human involvement as as we, as, as we need, and we want, I don't think, our goal is not to, to remove, as I said, our goal is not to remove humans from the loop. It's just to kind of move them to the top of their license.

[00:34:24] And so if, for example, the editor wants to. Um, get pitched four or five briefs from AOPs and give a 32nd whisper flow adjustment to the brief before the outline is even written. Then we should include that step if they want to see the finished product and just make, like, like edits because they've built a lot of trust or it's a, it's a, maybe it's a long tail piece of content, relatively simple.

[00:34:47] Um, then we can do that too. I, I think we are, we really want to bring people along and it, that means meeting people at their current level of comfort. I think the second thing I'll say is that the system has to get better over [00:35:00] time. And actually we made this mistake with the first version of AOPs where it didn't really get better over time.

[00:35:05] The more you used it as much as, as much as it needed to. We, with AOPs Next, which just launched, um, by the time this goes out, you know, the, one of the core design principles is that the more someone uses the system, the more it learns your style and starts to incorporate. Um, your, your kind of rules and things, even if you haven't explicitly told us them upfront.

[00:35:25] Um, a lot of people can't articulate what they want. They have to react to things to be able to, to kind of

[00:35:29] tease those out. And so that's a core design goal. But, um, you know, even if, even if it's, even if the, the brief is completely, uh, human written upfront, but we just use AI to battle, test that against the existing SERP to think about interesting references that can be included.

[00:35:46] And that's our starting point. That's great. That's, that's moving people forward and, and they'll layer

[00:35:51] on from there. So this is where the judgment is important and the incremental kind of layering of this is important.

[00:35:57] Jon: I wonder if, uh, you know, as you're [00:36:00] talking, I'm like, oh, I wonder what you, you think about the optimal places in these types of workflows to put the human in the loop. 'cause I think we're all on the same page here. Is that human in the loop, AI assisted, that's a path forward. It's not replacing people, it's augmenting.

[00:36:13] What do you see as being those opportunities where that human touch is a multiplicative factor? Just like AI can help us create 50 briefs at once, where does the human touch get the most bang for the buck in these, these new modern workflows?

[00:36:28] Alex: Yeah, I think AI is not very good out the box at ideation. Um, meaning that it, it's gonna suggest a lot of things you could write about and a very small subset of those by default are generally good, like very good ideas. Um, so I think that's one where we are a long way from AI kind of calling it sharp really well on, on, on great pitches for net new pieces of particularly editorial content.

[00:36:57] Like that's kind of, I, I think that's, you [00:37:00] can see a lot of volume there, but actually a high taste user is gonna have a lot of feedback there. So I

[00:37:04] think for sure, calling the shots on, on top of funnel content I, I think is very, very hard and, and want something that humans should be very involved in. Um, I think when it comes to, um, perspective as well and, and opinion, you know, the models are ultimately doing retrieval like chat.

[00:37:24] GBC is doing retrieval to get kind of frontier opinion and thought. And so there's a huge bias towards fresh content. Um, if you refresh content, you update the, the freshman signals, your chances of being cited increased massively. So that means that when you're creating a piece of content in AI workflow, figuring out who internally is the best person to add unique perspective to that and to provide some commentary and to provide a reaction, um, and attributed reaction, um, to, to add net new net new net new perspective to something is, is another very, very important one.

[00:37:58] But, um, I think [00:38:00] the goal here is to actually, um. Try and step out of at least some of those things over time that you are very hands on keyboard with initially. Um, once you get a little bit more confidence in, in, in how these things play out and, and are able to provide more guidance and context to the model.

[00:38:18] But certainly kind of top of funnel, like top of funnel query like ideation, I think is very hard. And then I think the, the, the kind of perspective and opinion and unique POV that's so important on top of all your internal grounding, again, is something that I think if you don't have it in loom videos or, or kind of internal resources is again, something that, that, um, should be added to most pieces to give it, to give it that authenticity.

[00:38:41] Phil: So you said Alex, that like in the early days it was just a couple of workflow steps and then you woke up at some point it was like a hundred plus. Um, you said in a couple other interviews that most of the workflows you see with clients and, and customers have 30 to 50 steps to produce what you're kind of calling excellent AI [00:39:00] optimized content.

[00:39:01] Maybe take us through like what you think are the most important first steps, like the early steps as part of the process and what's happening later on in the end. Like the final checks you just talked about, like human in the loop and, and where that kind of falls in. But like even without the human steps in there, like what needs to happen at the start and what are you kinda seeing Super important at the end.

[00:39:22] Alex: Yeah, I, I will, I'll say that by the time this goes I to, to everyone, uh, we will have moved on from workflows to a new structure for, uh, building these things out, which will look a lot more like natural language playbooks that will then, then run for you. We're trying to lower the bar to building these things.

[00:39:40] Um, but the structure remains pretty similar in the old world and the new world. I think. The most important, the most important sort of headline is being thoughtful about context gathering and preparation. Um, even in a world where you're using Claude or you're using ops or whatever [00:40:00] platform, um, is your, your tool of choice, um, being very thoughtful about where the right information lives, um, inside the business and outside the business is I would say 70% of the work and connecting up the right connectors, making sure the context is prepared, um, thinking about how to.

[00:40:20] Query that and, and make sure that you are, um, getting the right subset of that, that that internal knowledge is for a particular piece of content is very, very important. And often the content is internally is not ready for use by the lms. So there's often some prep work to do to make sure that, um, whether you are connecting directly to Google Drive, for example, or you are trying to get gong transcripts, um, making sure those connectors work well, you are thoughtful about how you go and fetch from those services.

[00:40:52] Um, and, and you, you sort of structure the, the retrieval process in, in a, in a, in a logical way is, is a huge amount of [00:41:00] the work. So I would say the first column is getting information from inside the business, and I would start simply with just a Google Drive folder with as much information as, as relevant as you have available.

[00:41:09] Like start with that single source of information and go from there. The second is collecting information on the competitive, uh, dynamics of the piece of content you're creating, right? So, so content needs to win in our view. Um, a particular keyword, a search, a query. Um, and so understanding what you're up against is important because you're not looking to create the same piece of content as everyone else, but there are certain clues in the content that's ranking that does tell you the kind of format that's expected, the sorts of like length that, that the kinds of topics that are probably expected by the algorithms to have in a specific dynamic, a specific situation.

[00:41:49] And so doing a deep. Audit, understanding what's happening there and just really like getting a, a sense of the what's included and what's not in the ranking [00:42:00] content gives you clues on what you should cover and where there's opportunity as well. Um, so that, that's your, those are your two, two of your biggest context sources internally.

[00:42:08] And then the, the sort of dynamic that you are competing, competing with. Um, and then how you bring that together is very much the next piece of, okay. Do we wanna start with pitches? Do we wanna start with, um. Maybe an outline that we're providing ourselves. Do we want to actually start with an interview guide for the team?

[00:42:27] Because often you'll want to go and get a lot of information to add to an article and have the AI basically craft a really great interview guide for one or three people, one, three people on your team. Um, and then it goes through the creation process. And, and a lot of folks are, are still going through the kind of brief to brief, brief, brief editing to article, um, drafting to, to revisions, to feedback, to publish.

[00:42:52] Um, and they can replicate that with kind of these human break points along the way. And actually the, the interesting thing is refresh works pretty similarly [00:43:00] as well. Um, so a lot of folks are doing refresh briefs, so they can be very specific about what's getting changed and why. Um, and, and being thoughtful about, you know, designing for human input.

[00:43:11] Um, and, and the sort of procedure you want to run is, is, uh, is, is a negotiation between, between members of the team participating in this.

[00:43:21] 5 — Why Review Becomes the Bottleneck After You Automate Content Production
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[00:43:21] Jon: O one of the things that jumps out at me as, as we're talking is as your customers have become successful with this, right? You talk about a three to four week onboarding period, there's probably a lag period before they've got their internal workflows all tuned up. So everybody's in the loop and then comes the rush, right?

[00:43:37] We are now 10 x more productive than we were six months ago. This is an experience that I've had in my own, my own small little shop here is like, the capacity is, is exploded. One of the limiting factors, uh, that I want your take on is attention. I, I increasingly see my own attention as being the limiting factors for the amount of work that I can accomplish.

[00:43:58] Like in theory, I could sit down and. [00:44:00] Publish out 15 articles, 20 articles in a day, which would've been a month's worth of work five years ago. But what, what gets you is the drain, right? The, okay, content switching, gathering information, refining. How do we see the role of like a content marketer, content engineer, evolving around this attention?

[00:44:19] Do you kind of agree that this becomes a limiting factor? Like I, I have a content calendar that I know I can execute against. I have the internal inputs, I have air Ops that does all the external research and, and validation, and now I need to sit my butt in the seat and do the work and manage all this stuff from briefs to even publishing it in a CMS.

[00:44:41] Alex: Yeah, I think it's so interesting, right? 'cause every time AI kind of takes one of these leaps forward, we are very good at instantly recognizing all the things it made easier. So all the friction that gets removed is like, oh, I get it. Like that, that job that used to take me three hours now goes to five minutes.

[00:44:58] What we're really bad [00:45:00] at, I think, is understanding where the friction moves in the system, um, and what's the new set of challenges that we need to solve. And so if you look at what's happened in engineering, traditional software engineering. Review is now the bottleneck for so many things. And just like literally just processing and focusing on is this good?

[00:45:16] Is this something we want to add to our code base so we don't spiral into like software slob? Um, and so I think this idea that the friction has moved in content creation to different parts of the system is, is very real. And this idea of of of like the review surface being one of the most important parts of the process to help people, um, accelerate, but also to make sure that it's an enjoyable experience, honestly, um, to go to is, is a core design goal of ours.

[00:45:46] And, and with our, with our new platform, because we recognize that a lot of. The work now is in thoughtfully, um, contributing, um, pushing back augmenting, like adjusting, uh, work that's happening in these, in these [00:46:00] AI systems to make sure that the brand isn't just getting diluted with noise. It's

[00:46:04] very important. One of the things with this AI search era is also that, you know, if you're just creating content that's, that's just, that's just ungrounded or it's off, or it's off message or the positioning is weak, you're just polluting your brand story. And

[00:46:18] so actually like getting review right and being disciplined about it and that being as an efficient process as possible is I think one of the new great challenges of this era.

[00:46:28] Also, if everybody has the same, so we're all very excited, we can create more content, but if everybody has the same tools and it's a competitive. Sport, you know, ultimately people have to reach deeper and get more creative to get the alpha and to really win. And so I think we are now beginning to understand how things like experiential content, video content, content that's like truly dis, dis differentiated and novel with great information gain is just getting more of a premium as I think the middle bar gets, uh, a little bit more, um, [00:47:00] accessible and commoditized to people irrespective of, of budget.

[00:47:02] So it's a very interesting time, but it's, al marketing's always involved, always been evolving, and this is just feels like a period of acceleration on that front.

[00:47:13] 6 — Why Enterprise CMS Integration Is Harder Than the Content Quality Problem
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[00:47:13] Phil: I wanna give you a chance, Alex, to talk about some of the technical details, uh, that lets air Ops stand out from some of the other competitive tools on the market here. Um, like one of the last mile steps that I haven't taken yet with my own little system is connecting everything to. My CMS, and that's really where I feel like you're unlocking a lot of the automation, right?

[00:47:37] Like outputting content in a text file or a markup file. That's one thing. And then having to like copy paste that in your CMS. It's a lot better than what we were doing before, but being able to have a direct MCP or API connection to our CMS and without having to log into it, refresh content, and run pipelines on that.

[00:47:58] I feel like that CMS integration [00:48:00] piece, it sounds really clean from the outside, but anyone who's actually tried to automate that last mile, especially with like headless CMS. There's like a schema problem. There's structured fields and tables and cells that are manually mapped. Like it's, there's a lot of like things and not to mention like IT policies and API access.

[00:48:18] How, how is AOPs solving this last mile publishing problem at like an enterprise scale? A lot of your customers are, are enterprise massive, team massive like, uh, content libraries where, you know, like there's technical constraints that are often more limiting than the content quality problem. What are your thoughts there?

[00:48:35] Alex: Yeah, I'll know we've hit a GI when, uh, it can post a, an article to an enterprise CMS, it's like, it's, it's I way, because I, I'm as a tools person, like tool legacy person, you know, I'm used to fantastic tools like Webflow super easy to integrate with, but you, you work with Enterprise and, and people have a three to six month lead time on adding a new page and you're like, how on earth are you guys gonna survive?

[00:48:59] Like, [00:49:00] we have to, we have to feed up it. We actually have four dedicated engineers who just integrate with Enterprise CMSs. That's

[00:49:06] all they do. And, and God bless them. Like it's, it's not for the faint hearted. These are like. Incredibly complex systems, and we build the, the pipes integrate with 'em. So for the easier CMSs is rolled out the box for the ones that are more, you know, uh, certainly have complex schemas and things.

[00:49:21] We, we, we build custom integrations, but both in terms of the data ingestion side, so the systems we can connect to for context, how we process that, and then how we push out final outputs. Um, that's a big part of the value we bring to, to allow these workflows and, and agents to go to go live. Um, and in the middle of our platform, it's broadly split up into three layers.

[00:49:42] We have. All the data we collect, we collect 2 million answers a day from AI search engines. We analyze them, we understand sentiment, drivers and citations, all that good stuff. We have our brand context layer, which is just added all visual brand, um, guidelines as well now. So you can create microsite and things off of it, and it's now [00:50:00] versioned and much more of a kind of govern source of truth.

[00:50:03] And then the third piece is the action layer, which we just relaunched to be agent first and allows people to get, have more ambitious use cases. And what we've observed is that each of those pillars is valuable kind of on its own, right? Like some people want two of the three, or they're using another tool or they like to work, you know, um, in their own setup.

[00:50:20] Um, but also people are working increasingly inside of things like Claude Code. And so every piece of Air Ops is available through an MCP. In fact, one of our customers ramp, um, actually runs all of their workflows. In AOPs directly through an MCP, and they orchestrate it all from their own system, and they're super, super happy.

[00:50:39] Um, and that's us kind of acknowledging that the top five, 10, 15% of users now are really racing ahead through personal AI enablement and, and things like Claude Cowork. Um, and, and we, we are excited to be part of that journey, but it's, it's not all happening in a UI anymore. A lot

[00:50:58] of people are on the CLI, A lot of people [00:51:00] are building in different ways, so I'm thrilled by it, but it does present a reinvention moment for us and the role we wanna play in that story.

[00:51:07] Jon: Uh,

[00:51:07] 7 — Why the Agent Runtime Is the Next Competitive Battleground for Content Teams
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[00:51:07] Jon: I want to dig a little deeper on the eugenic stuff that you mentioned. I think that's super

[00:51:11] fascinating. It's kind of an AI operator first mentality. I can't remember the last time I've signed into some of the software that I use, but I pay a lot of API fees.

[00:51:20] Alex: Yep.

[00:51:20] Jon: know Modern SaaS is, you know, especially on LinkedIn, we shouldn't trash it too much, but on LinkedIn, you know, modern SaaS is dead, is dying, it's

[00:51:26] going away forever. But I think that AI operators like myself, Phil, yourself, we're challenging the, the normal operating model. How much do you think that SaaS is gonna evolve to being like, Hey, I signed up Air Ops now I have an API call that I can use with cloud code that does 50 other things that are specialized versus we still work with within the UIs and, and evolve that way.

[00:51:48] Like the, i, I guess maybe not so much the future of software, but like how much do you think the, the market goes towards AI operators using terminal and then the software that either is built [00:52:00] specifically for AI operators or is just agnostic and can be used in both cases?

[00:52:04] Alex: This is a fantastic question and it's honestly, it's an existential question for stats to be honest and it, so we probably need another hour to talk about it. I think to my point, to my point about the friction moves in the system. I don't think anybody wants to review and approve feedback on a piece of content from a clawed code terminal necessarily.

[00:52:27] I think that would be like a pretty cumbersome experience. I also think that there's a lot of instances where, um, you know, specialized UIs can really help accelerate that review friction point that you, that you talked about. So, um, I think work is changing. I think the, the, this, there is this cohort of users such as yourself, John, who are working, um, with extreme leverage inside of their own setups.

[00:52:53] Um, but then content is also a team sport, um, that, that involves multiple people. There's a lot of kind of. [00:53:00] Interesting new challenges that are emerging around governance of context, where the skills live, how do they change, how do we know if they're good cost controls? All of these things that are sort of starting to become, um, new problems to be solved and SaaS needs to make sure as it's finger on the pulse on how the, how the, the challenges of getting to scale and getting to impact are, are evolving for us.

[00:53:22] Like I think there's a big piece of this is having data sets that don't exist anywhere else, um, to make sure that the content that's created is very competitive and understands how the things that needs to hit on in order to be successful. That's our kind of our insights layer. Um, and then, uh, the brand context piece we talked about, but I think that's ballooned in the last six months as being something that's really concerning for CMOs because they're seeing content go out that talks about their product in seven different ways.

[00:53:51] Um, and then for the actual agent runtime, I think. That there is an interesting question of, of where people will put their agents. And I think [00:54:00] right now we're, we are really in the sort of early innings of this with solo kind of local machine based agents, some early cloud agents, our bet is that we can build a better cloud agent runtime than anyone else for our use cases.

[00:54:13] And we've been working on that for six months. And I think buyers will become more sophisticated in how they think about where their agents are running. Um, both from a cost standpoint, observability, multi-party human in the loop, um, thinking about the data we can provide to those agents and also how they get better over time.

[00:54:34] So

[00:54:34] we worked with Anthropic very closely on this, this new launch. And I think what, what emerged as we were going through that is that, um, that the house that the agent lives in is actually gonna be one of the most important drivers of impact that will emerge in in the second half of this year. So, um, TTBD, but we're, we're

[00:54:53] pretty bullish on that.

[00:54:54] Jon: Fascinating. Fascinating.

[00:54:57] Phil: Yeah. Really cool to hear that. Alex, uh, got a [00:55:00] couple more questions for you. Um, I,

[00:55:02] 8 — What the Case Against Content Engineering Gets Wrong About the Role
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[00:55:02] Phil: I took a deep dive rabbit hole into content engineering in preparation for this conversation with you. There's one article that kept popping up in my research, uh, that was written by one of your competitors, and it's called, I wouldn't Hire a Content Engineer.

[00:55:16] Basically the Case against Content Engineering. His argument is like, the role is hiring for skills we won't need for a long time. He chose, he would choose. A great writer with no AI fluency over a middling writer who knows a lot of the agentic tools. What do you think he gets right in that article? I don't know if you had a chance to read it, but like where do you kind of disagree with that?

[00:55:39] Take?

[00:55:41] Alex: Yeah, I mean, I think I, I, I, I hope there is a role for great writers forever, and I think that there's a, you know, destination content that. Um, thoughtful. That really is like deeply invested in is, is a huge growth lever for businesses still. Um. I think in my mind, like [00:56:00] the, the, the, there's a lot of area under the curve first as a starting point that your best writers are not gonna have time to go get after.

[00:56:08] And what that gives you is basically a, a marketing asset that's decaying over time. So I don't, I, I, like, I, I actually haven't read this article. Um, there's been a few recent, uh, potshots of content engineering. Some of them misunderstand it, some of them are great critiques as we evolve this discipline.

[00:56:26] Um, but my general view is like, if you have a really great writer, hold onto the all costs and have them do work that is gonna be the most impactful they can and, and go as deep as possible. I would prefer to pair a great writer. With some content engineering and some agents in order to make sure they're really focusing on the right things.

[00:56:45] They're prepped to write, they understand the questions they should be answering, they understand the discourse going into a writing session. Then have them just sort of sit on a blank page and figure everything out themselves. And so it kind of is, again, falling into the, just skimming it now, it falls [00:57:00] into that trap of thinking.

[00:57:01] The goal here is to remove humans from the loop. I, I want more people in the loop in content, and I think that's, I want 'em to be doing really great work to create content that's differentiated, that gets picked up and gets cited. Not removing people and having the systems just spew out stuff that doesn't add anything.

[00:57:18] And it's just recycling the same talking points. Um, again, like the, the, the other piece is that I actually think that. Um, the most effective people in every discipline and knowledge work are learning some more systems and technical concepts. You can call that whatever you want. I do not have any opinion on changing your LinkedIn to content engineer as much as I love to see it.

[00:57:40] But the core principle here is, is that the mind of the writer is gonna have really creative, interesting ways to use these tools that, um, other people, other people probably wouldn't. And so, uh, our view is that the most successful folks will be a blend of the traditional art and taste and creativity and journalism with AI tools to, to, to really be able to leverage [00:58:00] their impact.

[00:58:00] Um, and that ratio will shift depending on the nature of the content task.

[00:58:08] 9 — What a Content Engineering Team Looks Like in 3 Years
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[00:58:08] Phil: are three years in the future. Alex, uh, a team that got content engineering really. Right. What does their team look like? Like head count structure, how the roles sit relative to to each other. You kind of mentioned like great writers paired with content engineers. Map that out for us.

[00:58:26] Alex: Yeah, so our, our, our, our view MS is that marketing teams will onboard a new org, like a, a new, a new subteam. And that team will be captained by one primary agent with a team of subagents that will help, um, run the operations of the marketing team. And I think realistically, people will have multiple agent platforms working for them.

[00:58:49] The one that we are standing up is, um, uh, the, the, the kind of content engineering team, content operations team. And the goal is to give, to be, [00:59:00] make sure that the humans and people in the loop are used as efficiently as possible. So they understand the shifts that are happening in the market. They understand competitor moves and the content that's being created.

[00:59:12] They understand where they're losing and gaining ground, and they understand the internal and external context shifts that should drive and prompt them to create content. And so. Uh, uh, my vision is that you have a really fantastic, uh, high, like extremely productive few hours inside of AOPs, um, where you come in and you are effectively given.

[00:59:34] Really great prompts and things to react to that can extract context. You can exercise your taste, you can add your, your whisper flow note on, on something you have as an opinion. You can get educated on what's shifting in the business. And that allows content to become a kind of more proactive system over time.

[00:59:50] And, and because it's just, and hopefully it's really fun. And when it's really fun, I hope more people want to get involved. More people in the company want to contribute their POVs, more [01:00:00] customers maybe want to contribute their

[01:00:01] perspective and we can actually make the kind of the maintenance of our brand story and the content footprint we have something that is just, is just, is just more energetic than it, than it is today where a few people have to like really bear the bulk of the burden.

[01:00:15] So, um, I think the big shift in AI systems we'll see within three years is that they become far more proactive. Trust increases as context and capabilities increase. And we learn how to work with them in a way that. Make sure that the brand we spent years building can, can, can kind of really thrive. And, um, and we have far more coverage than we do today.

[01:00:35] And the kinds of intents that we want to intercept. I really think most people are doing like 10% of what they could be doing if they really could scale themselves. And

[01:00:44] that will take years to get to. But, um, I think the future's really, really bright and exciting

[01:00:50] Jon: Uh, thinking

[01:00:50] of that content team and I'll, my la my last question, I guess, uh, for the, for the podcast, but one of the things in my own experience is I've been learning on the battlefield, right? [01:01:00] Getting that battlefield promotion because you're just figuring out like, oh, okay, this works, this doesn't work.

[01:01:04] I know you guys are releasing some training, and I think that's very much needed in, in the market. Do you feel like the space is evolving so quick that you know, what, what you're experiencing in 2026 won't be applicable in 2028? Do you think that things will carry forward, that foundational, Hey, I figured that this worked and didn't work, and then the model changes it?

[01:01:24] Like how, like how would somebody want to be on that team and three years from now train themselves to be an effective member of it? It's just being on the tools every day. Is it hands-on? Is it reps, is it taking a course? Combination?

[01:01:40] Alex: Yeah, I mean, I think it's, this is a question everybody's, I think asking, uh, in, in, in the kind of core knowledge work pillars right now. But, um, you know, I think you can doom scroll your way into getting into various head spaces that are ultimately unproductive. I think what is productive is treating [01:02:00] experimentation and learning as a core, just role a, a core duty that we all have now as professionals.

[01:02:06] And because this is such an interesting time, I think the more you can institutionalize play and experimentation in your week, the better. So we have play as a core operating principle at ops, and it doesn't mean going like. You know, build, build sandcastles and, and Lego buildings. But it does mean sort of follow your curiosity and try things and share what works.

[01:02:28] Nothing like lowers my blood pressure more than just using tools and building and trying things. Uh, and that's what we try and push our customers to do too. The, the upside of that is that you really get used to, uh, testing and learning and feeding that into your playbook and iterating because it will, it will shift, it will shift quickly, but also only you can really be the arbiter of good as a, as a marketer, I think.

[01:02:52] And so the best way to get confidence and evolve your playbook is to have, you know, maybe a few people on your team, maybe one person. Maybe it's you. [01:03:00] Just really carve out time to figure out where the value is in any given model generation, any given tool, and then work that into how you work. I will say that the spread of.

[01:03:10] Of adoption has never been wider. Like if you talk to

[01:03:13] the top 1% of marketers right now and you talk to the median marketer, that gap has never been, been, been bigger. Um, and, and there's gonna be many years of people making their way up that kind of adoption curve or AI curve. Um, and there's nothing wrong with that, right?

[01:03:29] I think it's, it's, it is, it is. Everyone's on their own journey, but making sure that we treat learning and, and sharing of learnings in teams as a core pillar, I think is, is super important.

[01:03:41] Phil: I love it. It's such a great answer, Alex. Um, really appreciate your time, uh, with us today.

[01:03:45] 10 — How Alex Decides What Deserves His Energy
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[01:03:45] Phil: I got one last question for you. You're obviously a founder, CEO speaker investor, but you're also a home chef, uh, at home and active fitness fee, and you got a ton of other stuff going on. One question we ask everyone is how do you decide what deserves your energy at any given moment, and what's your personal system for staying aligned with what actually makes you happy?

[01:04:06] Alex: Um. I think you have to, for me, I have to split my time between what gives me energy and what I have to do in my role. Um, I think this is where I have had to, as the business has gotten significantly bigger, got much better at prioritization, I actually have a personal open claw that's primary role is to help me prioritize, given

[01:04:26] all the noise around me.

[01:04:28] And I split the things I do in any given week between the, the, the, the, the sort of need to dos and the things that really give me energy and push my thinking. So back to the play point, I spend probably. The, probably the entire weekend day, um, per week, just building things in the business using our tool.

[01:04:45] Just kind of really following my curiosity, which gives me a lot of energy. And then in the week I'm spending time doing, you know, the other roles of of A CEO. Um, I do, I know everybody talks about kind of mind, body wellness community. I [01:05:00] think just like the assault on your psyche that running a startup is means that those things are so important.

[01:05:07] And I have had periods where I've neglected them much to my detriment, but this year I'm trying to be a whole person, get outside the West Side Highway is now open in New York as of as of the weather improving two days ago. So I'm, I'm very excited for, for the summer and, um, hopefully that feeds my creativity.

[01:05:23] It makes me a better leader. So it's a, it's a constant balancing act and I have my open claw to help me a little bit and it yells at me all the time when I don't do my, do my things.

[01:05:34] Jon: Yeah, so say we all.

[01:05:35] Phil: Yeah. I love it. Alex, thanks so much for your time today. Really appreciate it. Uh, we will, uh, obviously share out, uh, air Ops and all the, the new features that you kind of teased out for us today. Uh, but uh, yeah, really appreciate your time. Thanks so much for doing this.

[01:05:50] Alex: Such a pleasure, Phil. John. Nice to meet you both. This has been great.