Founder-Led

In this episode, we sit down with Christopher O’Donnell, Founder & CEO of Day AI and former Chief Product Officer at HubSpot, to unpack why CRM is being rebuilt from the ground up for the AI era.

Before starting Day AI, Christopher helped build HubSpot CRM, co-founded ProfitWell, and spent years thinking about how software can better serve sales, marketing, and customer teams.

What we cover:

➜ Why legacy CRM has become a system of delay
➜ What HubSpot taught Christopher about category creation
➜ Why AI-native software starts with workflows, not databases
➜ How founders can use AI agents to multiply output
➜ Why customer memory is the missing layer for agents
➜ The trust curve between humans and AI
➜ Why agents need context before they can take action
➜ How Day AI is reimagining CRM as a system of understanding
➜ Why small, nimble companies may have the biggest AI advantage

  • (00:01) - - Introduction to Founder-Led Podcast
  • (00:08) - - Sponsored by Frontier Content Studio
  • (00:33) - - Guest Introduction: Christopher O'Donnell
  • (01:40) - - Christopher's Journey Through Tech
  • (03:04) - - Learning from HubSpot CRM Development
  • (06:37) - - Transitioning to Day AI
  • (07:00) - - Reimagining CRM for SMEs
  • (09:32) - - The Role of AI in Business Growth
  • (11:10) - - Workflow Automation for Founders
  • (12:25) - - AI's Impact on Sales Processes
  • (15:10) - - Personalizing Sales Outreach with AI
  • (18:06) - - Building Trust in AI Interactions
  • (21:45) - - The Future of AI and Human Collaboration
  • (24:47) - - Time to Value with Day AI
  • (30:08) - - The Role of Professional Services
  • (34:39) - - Final Thoughts and Future Outlook
  • (35:55) - - How to Connect with Christopher

If you’re a founder, operator, or GTM leader trying to understand how AI will reshape sales, CRM, and customer relationships — this conversation will change how you think about your tech stack.

Recommended Resources:

➜ Christopher O'Donnell: https://www.linkedin.com/in/markitecht/
➜ Day AI: https://day.ai

Connect with Rohan:
https://www.linkedin.com/in/rohankarunakaran

What is Founder-Led?

Welcome to Founder-Led, featuring founders scaling 7 and 8 figure companies who share the strategies and mindset driving real growth.

Brought to you by LinkedIn Growth Engine. We help established recruitment and staffing firm owners land new clients from LinkedIn by turning their executive content and insights into a trust building inbound lead engine.

We partner with $1M to $20M+ agency founders to build visibility, authority, and trust that drives pipeline, without turning you into a “content creator.” Over the last 12 months, we've helped drive $20M+ in booked revenue from LinkedIn.

If you're done relying on referrals and want prospects coming in pre sold, you're in the right place.

https://www.youtube.com/@rohan_karunakaran

00:00:01:16 - 00:00:08:21
Rohan
Welcome to Founder Lead, where we sit down with some of the sharpest founder operators to learn what's working in their business today.

00:00:08:21 - 00:00:12:17
Rohan
This episode is brought to you by Frontier Content Studio,

00:00:12:17 - 00:00:14:17
Rohan
a revenue minded content partner

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Rohan
helping businesses grow their visibility,

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Rohan
authority

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Rohan
and ultimately demand for their products and services from LinkedIn.

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Rohan
if you're ready to join over 40 businesses

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Rohan
are turning thought leadership conversations

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Rohan
like this podcast

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Rohan
real demand,

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Rohan
common frontier below

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Rohan
someone from our team will reach

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Rohan
Now let's get to today's episode.

00:00:33:10 - 00:00:35:17
Rohan
Today we're joined by Christopher O'Donnell,

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Rohan
co-founder and CEO of day AI.

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Rohan
Before starting day, Christopher spent more than a decade at HubSpot helping build HubSpot CRM and eventually serve as their Chief Product Officer.

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Rohan
Along the way, he learned what it takes to build conviction around a new category before it's obvious

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Rohan
what creating something new inside a larger company really demands.

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Rohan
this conversation, we talk about what building HubSpot CRM taught him about category creation,

00:01:02:21 - 00:01:05:00
Rohan
where legacy CRM fall short,

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Rohan
with the future system of record and action looks like in this next generation of software shaped by AI.

00:01:11:15 - 00:01:13:02
Rohan
Christopher, welcome to the show.

00:01:13:04 - 00:01:15:19
Christopher
Great to be here, Ron. Thanks so much for having me

00:01:16:01 - 00:01:21:13
Rohan
Yeah, really looking forward to our conversation today. You know, maybe as a jumping off point, you've got such

00:01:21:13 - 00:01:40:11
Rohan
an impressive track record from building HubSpot CRM to then co-founding profit. Well, exiting that for $200 million bootstrapped and then CPO at Thrive Global. Talk a bit about what the through line is there, and then maybe what kept you coming back to the CRM opportunity?

00:01:40:14 - 00:01:41:21
Rohan
Yeah, I mean, I.

00:01:41:23 - 00:01:46:09
Christopher
Just answer the phone when it rings, I guess, you know, I didn't

00:01:46:09 - 00:01:54:01
Christopher
dream of being a product manager when I was a little boy. You know, I wanted to build airplanes and design sailboats and later

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Christopher
take guitar solos at, you know,

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Christopher
stadium or something like that. So I backed into software. My background is mostly in music, and I found that leading software teams and all the creative personalities and opinions was

00:02:11:09 - 00:02:16:14
Christopher
basically exactly the same as being in a recording studio, trying to write an amazing song.

00:02:16:15 - 00:02:23:18
Christopher
So that's where you'll find me. Somewhere where I feel like I can bring my friends and build something of value.

00:02:23:22 - 00:02:36:20
Christopher
That's brought me into sales and marketing tech, where I've spent most of my career. And you know what better way to be of service, you know, to people, is to build workflows and,

00:02:36:23 - 00:02:42:19
Christopher
you know, software automation to help them be of better service to the people in their lives.

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Christopher
And, you know, to speed up the way that they are feeding their families and give them more hours back in the day.

00:02:48:11 - 00:02:59:08
Christopher
And, yeah, I mean, it's a very different time that we're in now. And I feel like the rules, many of the rules don't apply anymore. But that's still why we come in every day is to just try to do something of service.

00:02:59:10 - 00:03:04:22
Rohan
Yeah. So, yeah, take us back to your days at HubSpot because, you know, HubSpot, its

00:03:04:22 - 00:03:11:01
Rohan
iconic technology company and the market leaders with CRM and marketing automation. So

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Rohan
what was the kind of like skunkworks projects that you built up there with the CRM opportunity? What did selling it internally look like, and what did you learn from that

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Rohan
that you're bringing forward today?

00:03:23:05 - 00:03:32:03
Christopher
Yeah, I had three chapters at HubSpot. So the first was coming through an acquisition and doing a reply form, sort of a rapid reply,

00:03:32:07 - 00:03:45:02
Christopher
very hands on, on keyboard. We didn't have, you know, designers and support specialists and product marketers and everything like that. I got to sort of do it all, design the API contracts with my friends.

00:03:45:03 - 00:03:46:19
Christopher
The second chapter

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Christopher
was really around the time we went public, kind of throwing the fish back in the water and starting over,

00:03:53:23 - 00:04:13:22
Christopher
and the founders had a couple of really interesting goals. One was to walk the hall and have a second act to shamelessly mix metaphors here, but to do something outside of marketing, you know, back in 2013, 2014, a HubSpot, there was no marketing hub, it was just HubSpot.

00:04:13:23 - 00:04:26:16
Christopher
It was entirely a marketing platform. And, you know, every year as we talked to customers, more and more people would say, you know, if you just did this and just did this, you could have a sales solution. I could get rid of my CRM.

00:04:26:19 - 00:04:39:12
Christopher
And so the founders had a very clever idea to let us go hang up a pirate flag, which we literally did build on whatever stack we wanted and go after this sales technology

00:04:39:12 - 00:04:44:21
Christopher
category in sort of whatever ways were interesting in the building.

00:04:44:21 - 00:05:17:15
Christopher
So there were a lot of different interesting ideas. There was core CRM, Salesforce automation, you know, system of record category, and also all of these really interesting sales enablement, sales acceleration point solutions that seemed really neat and were were being adopted from the bottom up through an organization. And that was the second part of the charter, was to figure out kind of a bottom up motion as we went multi-product, which made it just wildly interesting and hard, frankly, really, really hard.

00:05:17:17 - 00:05:21:10
Christopher
And then along the way, you know, there was the big decision of whether to

00:05:21:13 - 00:05:33:14
Christopher
build on top of other Krems, you know, one in particular, or to just go all in on building a core system of record CRM product.

00:05:33:17 - 00:05:34:13
Christopher
I think

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Christopher
we made the right decision. The founders of HubSpot made the right decision to do core CRM, and then made a really gutsy decision to make it free.

00:05:43:10 - 00:05:49:00
Christopher
So then this whole bottoms up DNA that we had been kind of trying to develop

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Christopher
was, was in the fold at that point.

00:05:51:17 - 00:06:08:22
Christopher
And then a few years in trying to merge these two entities back into one overall go to market beast. I mean, there are many chapters in there. I'm happy to explore any, any part of it that you like, including moving our entire public company to this new CRM

00:06:09:03 - 00:06:09:19
Christopher
system

00:06:09:19 - 00:06:12:00
Christopher
off of another CRM system

00:06:12:02 - 00:06:13:21
Christopher
that you can guess pretty easily.

00:06:14:01 - 00:06:17:14
Christopher
So yeah, just a lot of trials and tribulations. It was

00:06:17:14 - 00:06:21:18
Christopher
it was fun. It was it was pretty hard. But we had a lot of autonomy,

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Christopher
a very clear charter,

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Christopher
our own team. And then we sort of, you know, merged team by team back into the mothership.

00:06:29:16 - 00:06:36:18
Christopher
And yeah, no, there's there's a lot there to dive into. There's now a Stanford Business School case study on on that chapter.

00:06:37:00 - 00:06:42:00
Rohan
Yeah. Okay. Yeah. Very cool. Well, what I want to do is just bring it forward now to present day

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Rohan
Okay. So, you know, most of our audience I want to make it practical for them. They are SMEs, right. Anywhere from single founder operators doing less than million dollars up to about $40 million run rate. So talk a bit about how you're reimagining CRM to make it more natural

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Rohan
in terms of how someone interacts with it and ultimately how you're giving the individual superpowers where before they might have felt constrained with the user experience or other tools or integrations.

00:07:10:23 - 00:07:13:18
Rohan
How are you thinking about just like reimagining it to make it feel

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Rohan
like magic?

00:07:14:21 - 00:07:32:18
Christopher
Yeah, if you're listening to this and you are one of these founders business owners in your earlier stage, you still have a lean team. You know, there's a really good chance that you can be a mammal as the asteroid hits and, you know, extinguishes the dinosaurs.

00:07:32:23 - 00:07:34:19
Christopher
You know, why is that? Well,

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Christopher
if you're a big established company, obviously it's hard to change quickly.

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Christopher
Yeah. But you also have these functions already built out. And one of the advantages that you have as a newer, lean, earlier stage company is that you're still building these functions out, which means there's enormous

00:07:56:13 - 00:08:06:00
Christopher
green field that you can fill with AI because there's nothing there yet from your own time as you start to specialize your time.

00:08:06:01 - 00:08:19:18
Christopher
You know, as founders, we do everything you know for the first year or years, and eventually you need somebody who really knows marketing to run marketing, you need somebody who really knows engineering to run engineering, whatever it may be.

00:08:19:22 - 00:08:30:15
Christopher
Now, you don't necessarily need to build the financial model of 5 or 10 years ago and then drag the spreadsheet and raise money and sort of play that that same game.

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Christopher
In fact, I think it's really not an option anymore. So

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Christopher
so, you know, what do we do?

00:08:37:20 - 00:09:00:06
Christopher
Everybody sort of has this sense that there's this techno hyper elite cabal somewhere running all of these AI agents on Mac minis and everything like that. And to a large extent, that is true. A lot of these Bay area Silicon Valley founders and, you know, quad code sickos that are out there have a lot happening around the clock.

00:09:00:06 - 00:09:04:21
Christopher
Even, you know, today, Q1, Q2 of 2026,

00:09:05:00 - 00:09:07:09
Christopher
it's pretty approachable

00:09:07:12 - 00:09:33:02
Christopher
to have this running for you and for all of your employees. And as you grow, each person that you bring on can realistically do two or 3 or 5 times as much work as they could in a previous world, especially if they are coming in with no baggage, no org structure, no layers of management.

00:09:33:04 - 00:09:39:06
Christopher
You know, we're hiring a head of marketing this week. He's joining. And this guy is super brilliant.

00:09:39:11 - 00:09:56:11
Christopher
He may be the only marketer we ever hire. Yeah. You know what I mean. Because he can manage agents and he can manage contractors and vendors who themselves are basically managing agents. Agents are managing agents now. Yeah.

00:09:56:14 - 00:09:59:20
Christopher
Reality. And this is now practical, you know, as of

00:09:59:23 - 00:10:06:04
Christopher
February of 2026, as we move into the, you know, the meat of the year in the back half of the year.

00:10:06:05 - 00:10:10:08
Christopher
This is available and approachable, and there are ways to do it that are safe,

00:10:10:13 - 00:10:12:13
Christopher
that are grown up, you know,

00:10:12:13 - 00:10:22:21
Christopher
and that really scale and ways that you can give a new employee one or more of these virtual team members with clear job description, with

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Christopher
clear role and responsibilities that will communicate with that colleague that you add to the team who's in charge of that AI agent and very clear ways email slack.

00:10:33:08 - 00:10:37:12
Christopher
You know, probably within a year we'll be doing voice calls with these AI agents.

00:10:37:14 - 00:10:40:03
Christopher
Yeah. So it's a very different mental model.

00:10:40:05 - 00:10:47:17
Rohan
Okay. So let's make it real. Now. You know, oftentimes our founders are wearing multiple hats right. Sometimes they're creating content.

00:10:47:17 - 00:10:52:19
Rohan
They are building lead lists. They are doing outreach personalized emails. And

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Rohan
on top of like building the product roadmap with their company. So

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Rohan
let's take a workflow that exists right now. Let's just say, you know, sales, the sales motion where there's some level of like an STR and outbound and then personalized emails, of course, like the tools are making it better to personalize and make things a bit more efficient.

00:11:10:23 - 00:11:12:14
Rohan
But how do you see

00:11:12:19 - 00:11:21:16
Rohan
maybe like a founder that's doing founder led sales now using this CRM alongside an agent or a team of agents to

00:11:21:19 - 00:11:22:04
Rohan
just

00:11:22:04 - 00:11:25:18
Rohan
augment their workflow or just get a lot more done, what does that look like?

00:11:25:20 - 00:11:32:22
Christopher
Yeah, and all of the workflows that you mentioned are things that we have agents for ourselves

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Christopher
helping us with and doing a lot of a lot of that work product for sales, for founder led sales in particular.

00:11:39:22 - 00:11:48:16
Christopher
You mentioned a couple of pieces of this, so let's take each one. One of the things you need to do in the early stages as a founder, find product market fit.

00:11:48:16 - 00:12:14:01
Christopher
And coming out of that realization, that moment of product market fit, develop a sales process that you can add bandwidth to. So we start out just kind of doing customer development, doing very open ended, don't lead the witness kind of interviews, and you end up with a head of sales who is hiring salespeople, who go through training and are able to get on the phone and do discovery and pitch and sell this thing in ways that are predictable.

00:12:14:01 - 00:12:25:11
Christopher
It's that kind of journey. So, you know, this is one of those examples where I really always encourage people to raise their expectations of what is possible with the AI.

00:12:25:16 - 00:12:35:00
Christopher
If you kind of mess around Weekend Warrior with ChatGPT and that kind of thing, maybe help your kids make coloring books, you know, do some neat stuff.

00:12:35:04 - 00:12:35:16
Rohan
You may.

00:12:35:16 - 00:12:38:04
Christopher
Not be thinking big enough.

00:12:38:04 - 00:13:01:05
Christopher
So for that, pipeline development in AI, agent should be able to design this sales process for you and with you, and iterate from point A to point B all along the journey. Just do some calls, just see how it goes, talk to the agent, say, okay, I want to kind of put some bones around this, work with me on that.

00:13:01:05 - 00:13:03:04
Christopher
And the agent will say, listen,

00:13:03:07 - 00:13:19:09
Christopher
let's think about how about we do this? How about we do these stages. This is how we think about each of these stages. This is the purpose of this pipeline that we'll make together. And then you just go back to doing your calls. I'll prep you for your meetings. I'll help you do all of your follow up.

00:13:19:09 - 00:13:24:12
Christopher
I'll help you synthesize what you're learning across this. And maybe most importantly,

00:13:24:16 - 00:13:58:13
Christopher
I'll create the opportunities. I'll move the opportunities through this pipeline. You don't have to do any of that administration. But creatively, let's talk about what we're learning and iterate on this process so that that pipeline isn't just a Trello board. You know what I mean? That it has real definition and meaning, and that that definition and meaning grows from early product market fit discovery to predictable revenue, you know, world class, scalable pipeline that you can actually give a team.

00:13:58:18 - 00:14:17:09
Christopher
These foundation models are good enough to do that now, especially with the models we got in the first week of February here. You know, things like the four sixth generation of the anthropic models. Yeah, I mean, they know as much about how to think about a sales pipeline as pretty much any consultant

00:14:17:09 - 00:14:20:09
Christopher
on Earth. I mean, this is very humbling, but they know a lot.

00:14:20:13 - 00:14:22:16
Christopher
Yeah. So that's one

00:14:22:16 - 00:14:41:04
Christopher
on the prospecting side. You know, the old world, you buy a list, you know, you personalize the list or you get one of these AI beads or something and they don't really do a ton. I get these emails all the time, I don't I send some of these, I don't send many of these,

00:14:41:04 - 00:14:45:08
Christopher
but I get these emails constantly and they are not good.

00:14:45:09 - 00:14:53:20
Christopher
I have been getting cold emails and cold calls for years and years. I'm on all of those lists despite opting out. And

00:14:54:01 - 00:14:59:16
Christopher
you know, it's just brute force is still the name of the game in the new world.

00:14:59:21 - 00:15:10:16
Christopher
Let's take that same agent that was working with you, building that pipeline, managing that pipeline. That agent is hyper intelligent and will start to see patterns.

00:15:10:18 - 00:15:24:12
Christopher
And that becomes the conversation, you know, not just, hey, I move this deal. Yeah. Because you had a call and you sent a DocuSign. So I moved it into, you know, the next deal stage. It's,

00:15:24:15 - 00:15:42:08
Christopher
you know, what's working for you is when you meet somebody who is a former operator and they're kind of from this kind of background, and they've started a company and they're at this inflection point with the company, and you get onto this strain of conversation.

00:15:42:09 - 00:16:04:05
Christopher
That is really an amazing pitch. What do you say we go find 50 more people who fit that profile? And you say, that sounds like an incredible idea. And then it's deep research to find those people, evaluate them, and you're actually drafting those emails based on who that person is and not just some, you know,

00:16:04:08 - 00:16:07:23
Christopher
I see I see from LinkedIn that they're a dog owner, you know what I mean?

00:16:08:00 - 00:16:08:21
Christopher
You know, or like

00:16:09:02 - 00:16:13:00
Christopher
I mentioned, the pizza shop in their hometown, you know, but really,

00:16:13:03 - 00:16:33:01
Christopher
really synthesized. Here are the promises in the pain points that have worked for her, her and him. And this person looks like them. And I'm going to look deeply at them. I'm going to do a ton of research on them. And then I'm going to write an absolutely, insanely good email to that person.

00:16:33:03 - 00:16:53:00
Christopher
And I'm going to say to the human here to, you know, the founder leading this, here's how to think about this campaign. We're going to do 50 of these. I'm going to write these emails. You can review them. We're going to track the whole campaign. You know, every morning. Let's make progress on this. I'll to you up or I'll do this automatically or whatever.

00:16:53:00 - 00:16:55:23
Christopher
And it's all flexible. You can just say,

00:16:55:23 - 00:17:07:04
Christopher
I don't really think of it that way, and the whole thing adapts. Right. And that's I think what's about to hit the world is this level of adaptive orchestration.

00:17:07:07 - 00:17:09:13
Christopher
That is much more than, you know,

00:17:09:18 - 00:17:14:06
Christopher
you know, Claude Webb or something like that, which, I mean, it's an incredible product,

00:17:14:11 - 00:17:15:03
Christopher
you know what I mean?

00:17:15:04 - 00:17:20:23
Christopher
Yeah, exactly, exactly. And adapting to your feedback, as you say. You know, that's not

00:17:20:23 - 00:17:32:09
Christopher
I don't really think that's an opportunity or I wouldn't qualify that. I don't like that one. Tell me why. Okay. Let's update our notion of an ICP. Let me look at your pipeline. Clean it up. How about I clean these

00:17:32:09 - 00:17:33:14
Christopher
off? Yeah, that sounds good.

00:17:33:15 - 00:17:35:19
Christopher
It becomes this back and forth.

00:17:35:19 - 00:17:43:04
Christopher
That's that's really exciting. And you can do that for sales. But you can do that for marketing. You can do that for products and on down the list.

00:17:43:06 - 00:17:44:14
Rohan
Yeah. So

00:17:44:17 - 00:17:58:16
Rohan
this is such an interesting and relevant point because we have many again, founders that are reevaluating their tech stack. Right. And there's so much pressure now to hearing open cloud here. And you know some other autonomous agent agent theirs. And a lot of them are thinking, how do I

00:17:58:19 - 00:18:06:10
Rohan
just get our business ready to to make sure that we seize this opportunity, but also make sure that we don't get leapfrogged by another, more nimble competitor?

00:18:06:10 - 00:18:07:04
Rohan
So

00:18:07:08 - 00:18:17:00
Rohan
where do you. Where do they draw the line? I guess the question is also, now there's this kind of like trust layer that's developing alongside the the AI layer. Where do you t

00:18:17:00 - 00:18:30:15
Rohan
up the email for the human to then click send now? Or do we now empower agents to be an STR where there's some they're kind of like have that autonomy and control to have a conversation with a prospect.

00:18:30:16 - 00:18:31:23
Rohan
What does that look like?

00:18:32:02 - 00:18:36:00
Christopher
It's a terrific question. And this is one of the.

00:18:36:00 - 00:18:36:15
Rohan
Key.

00:18:36:18 - 00:18:51:17
Christopher
Questions and challenges, I think, in business software, SaaS, product development today, they never existed. You know, two years ago, it never existed. I mean, we built the first version of De AI.

00:18:51:21 - 00:18:53:15
Christopher
We built a meeting recorder

00:18:53:17 - 00:19:02:13
Christopher
with an eye toward certain types of synthesis and quality of notes that came out of it. And then we built this self-driving CRM.

00:19:02:15 - 00:19:09:02
Christopher
And the third thing that we've built is this a genetic layer that is really intuitive.

00:19:09:04 - 00:19:23:22
Christopher
And one of the things that we learned in the self-driving CRM phase of this, I have to admit, we thought, okay, we've been doing this a long time. If we have a CRM that is automatically populated top to bottom, everything moves on its own.

00:19:23:22 - 00:19:25:18
Christopher
It's like the Waymo of CRM.

00:19:25:23 - 00:19:27:06
Christopher
People are going to love this

00:19:27:11 - 00:19:31:20
Christopher
if that's all you do. People do not love it. They do not love it.

00:19:31:20 - 00:19:35:02
Christopher
I would not love being in a Waymo and

00:19:35:02 - 00:19:36:17
Christopher
having curtains around me.

00:19:36:21 - 00:19:37:15
Rohan
Yeah, right.

00:19:37:16 - 00:19:48:04
Christopher
You need to have some sense of security and trust. You need the little monitor that shows that it knows there's a dog in the road. Right? You need to be able to look out the window.

00:19:48:06 - 00:20:02:02
Christopher
And then actually in software you need to be able to you can't do this in a Waymo. I think you'll get arrested. But you know, to be able to grab the wheel and say, let me drive for a bit and pick up on kind of how I want to do things, and then and then let go of the wheel.

00:20:02:02 - 00:20:21:12
Christopher
And it adapts to the way that you were driving. So that was an enormously deep layer that needs to be captured in exposed. Why is this data what it is? Where did it come from? You know, you need to be able to see some custom property value or one that your agencies.

00:20:21:14 - 00:20:23:11
Rohan
And to immediately.

00:20:23:11 - 00:20:36:06
Christopher
Click a citation and see a moment in a meeting where somebody said a thing and it's like, okay, that's why this discovery question is answered this way, because they set it. Yeah. And I can trust it.

00:20:36:08 - 00:20:45:12
Christopher
So the trust curve and you're right, I think where you're trying to thought of is going is exactly right. The more people trust it, the more they'll let go of the wheel.

00:20:45:16 - 00:21:06:01
Rohan
Yeah, that makes that makes complete sense. And we're already seeing it with the frontier LM labs. Right. We're seeing more context become available and more transparent during the the reasoning and the output to be like, okay, it's referenced these project files or it's pulling these web sources or whatever it is. And so that makes a lot of sense to continue to release some of that trust.

00:21:06:01 - 00:21:08:02
Rohan
And then I guess there's also a

00:21:08:05 - 00:21:30:08
Rohan
an evolution and maturity that happens where on the other side of it, a prospect would feel comfortable interacting with an agent if they're getting much more responsive, personalized experience, I think ultimately comes down to the experience, right? Like we've seen it through the arc of technology, whether it's, you know, Netflix giving us a much better kind of home page than a static TV channel or whatever it might be.

00:21:30:08 - 00:21:45:20
Rohan
And so how does this play out in a world where every interaction we have is personalized to me, my buying needs and what this agent can uniquely give me given my context, the company's context, and just being available 24 over seven, would that be a fair way to think about it?

00:21:45:22 - 00:21:50:01
Christopher
100%? There's no trust me, bro, you know there's no

00:21:50:01 - 00:21:50:11
Christopher
you know,

00:21:50:14 - 00:22:02:09
Christopher
the models are amazing. You know, we have the capability to automatically send emails. And I was just putting in a ticket for us to really have the conversation about turning it on for people.

00:22:02:09 - 00:22:17:02
Christopher
You know, we sort of take this Hippocratic oath of to first do no, do no harm and to be a little bit, a little bit careful with, you know, giving people things that if they use them in ways that surprise them or whatever,

00:22:17:08 - 00:22:19:10
Christopher
you know, could, could go wrong.

00:22:19:10 - 00:22:48:05
Christopher
And we're going to have to turn this on because people are like, look at this. This email is incredible. So I'm not trying to like tout our thing. I mean, a lot of it has to do with the foundation models and having the right context. We all know that one of these, you know, the super high test models right now, if you had every snippet of background for a relationship, if you had exactly the sentences that mattered, then this happened.

00:22:48:06 - 00:22:57:04
Christopher
Then they were concerned about this. Then their role changed in the company to this. Like if you had that all these foundational models would

00:22:57:08 - 00:23:02:04
Christopher
write an unbelievably good email based on your goals. We all know that.

00:23:02:04 - 00:23:07:20
Christopher
So we do that, we orchestrate that. But, you know, a lot of the credit goes to the foundation models along the way.

00:23:07:23 - 00:23:13:07
Christopher
People are like, these emails are unbelievably good. Just send them, just send them.

00:23:13:07 - 00:23:13:15
Rohan
I get.

00:23:13:15 - 00:23:20:04
Christopher
It, I get it, I get it. So we're starting to see a lot of that, right in terms of the adaptability.

00:23:20:09 - 00:23:20:14
Rohan
Yeah.

00:23:20:16 - 00:23:54:11
Christopher
And even designing things hopefully elegantly in a way where the agents start out by saying, here was a thing that I was about to do, and I just want your feedback. What do you think? Yep. And then the person says, yeah, that looks good. Or am I don't think that's an OP, but let's talk about it. Should I think, you know, and they go back and forth and then the agent develops this sense of confidence while the human is developing a sense of confidence that has to happen together.

00:23:54:14 - 00:24:18:14
Christopher
We're learning in in the design of these skills. Right. As these things come online. It's like the first version of a skill maybe is here's the skill we want this to be. But your job is to actually work with the user and get to a point where this skill is the edited version of this that you just fire and forget.

00:24:18:16 - 00:24:33:07
Christopher
So anyway, it's fascinating stuff and trying to get the psychology right. People respond so much better to AI work product that is being done in the context of their ownership, in the context of their

00:24:33:10 - 00:24:47:22
Christopher
feeling as though they had editorial feedback, stylistic feedback, and in a level of taste that went into the thing that they're looking at. They have a very different kind of emotional response to it.

00:24:47:23 - 00:24:57:03
Christopher
Yeah, this makes a lot of sense. I was just speaking to a, a founder who's reimagining corporate travel, and they're building autonomous agents to help,

00:24:57:03 - 00:25:05:11
Christopher
you know, these big consulting firms and their consultants, but corporate child in a much more natural way. And he talked about this idea where

00:25:05:14 - 00:25:12:08
Christopher
you're making it, as, you know, the agent is taking on more and more responsibility in terms of finding the right hotel, certain location, the right flight.

00:25:12:09 - 00:25:29:00
Christopher
At a certain point, the consultant might want to take a look at the plane's seat map because they want, based on some level of how full it is. They might want economy because there's a likelihood that might get upgraded to me. Plus. Right. And also just like legroom and all these sort of things. And so it was interesting to hear how

00:25:29:03 - 00:25:33:17
Christopher
in these early stages, humans want to be involved in certain points of the booking process.

00:25:33:17 - 00:25:52:11
Christopher
But eventually, once the agent learns their preferences, they release more and more control. And now they have the human click like book now. But the feedback they're getting is no. Like, just handle it right. It's not like this is a fun vacation I'm booking. This is like every week I'm flying to this location. I don't want to be thinking about it.

00:25:52:11 - 00:25:54:14
Christopher
If it can be booked, you know

00:25:54:14 - 00:26:08:05
Christopher
better than how I would make that decision. So it sounds like there is this maturity that's happening across all these different industries where people are willing and actually very happy to release that control when these agents are making

00:26:08:08 - 00:26:10:14
Christopher
these great decisions. So that makes a lot of sense.

00:26:10:19 - 00:26:17:11
Christopher
It's a little bit like training a new colleague, honestly, or a new sort of supervise the way that,

00:26:17:11 - 00:26:20:04
Christopher
you know, there are all these frameworks for for management.

00:26:20:04 - 00:26:37:10
Christopher
And, you know, you start very in the details, doing the job side by side. And over time you sort of delegate and give more freedom. There are a million of these frameworks, right? And they all sort of say the same thing, which is don't start with a ton of freedom and then come in and micromanage,

00:26:37:15 - 00:26:41:12
Christopher
micromanage, and be clear that you're going to micromanage at the beginning.

00:26:41:12 - 00:26:53:07
Christopher
And then as you see mastery in a particular task or goal, then you start to give that freedom an autonomy and still with trust and verify. And I think all of those

00:26:53:10 - 00:27:01:07
Christopher
techniques or inclinations, patterns still apply here with the AI. And it works really well for the AI,

00:27:01:07 - 00:27:08:21
Christopher
and it gets all the clarity that it needs to book a flight, to order a meal, to create an opportunity, whatever it is.

00:27:09:01 - 00:27:19:07
Christopher
And we feel more comfortable with it for the same reasons that we feel more comfortable with an employee who we have trained and sat with doing the work.

00:27:19:11 - 00:27:21:04
Christopher
Yeah, yeah. So,

00:27:21:07 - 00:27:30:09
Christopher
you know, as we start to wrap it up here, Christopher, I want to, you know, you being a product leader, I'm curious to know with with day like what is that time to value.

00:27:30:10 - 00:27:44:10
Christopher
Maybe talk about a couple of customer stories where there's been some moment or some interaction. It's like, oh wow, this is so much better than what I'm used to. Or how do you even think about tracking time to value or other metrics that, you know, that usage is healthy?

00:27:44:13 - 00:27:47:11
Christopher
Yeah. I mean, the time to value is is massive.

00:27:47:15 - 00:27:50:05
Christopher
People should be able to come in

00:27:50:08 - 00:28:02:00
Christopher
knowing that there is some work product, some productivity to be gained in their role through AI, not know exactly what it is.

00:28:02:04 - 00:28:05:07
Christopher
Sign up, connect their data and

00:28:05:10 - 00:28:06:16
Christopher
be shown

00:28:06:19 - 00:28:14:22
Christopher
what that work product is, and have a conversation within 24 hours where the agent is saying,

00:28:15:02 - 00:28:16:19
Christopher
here's what I've done for you.

00:28:16:23 - 00:28:19:18
Christopher
Here are other things I'd like to do for you.

00:28:19:22 - 00:28:21:03
Christopher
Talk to me

00:28:21:05 - 00:28:24:04
Christopher
and then it's just a back and forth.

00:28:24:08 - 00:28:26:09
Christopher
Part of the trick here is

00:28:26:12 - 00:28:36:12
Christopher
humans want to be very involved in the definition of the behavior of these AI agents, but we are not very good at defining that behavior.

00:28:36:17 - 00:28:44:23
Christopher
We are not walking around saying, oh, I have a brilliant idea for an open claw skill prompt or something like that.

00:28:44:23 - 00:28:49:11
Christopher
The AI is actually better than we are at. That

00:28:49:11 - 00:28:52:15
Christopher
part of it is AI is very good at configuring AI,

00:28:52:18 - 00:28:53:09
Christopher
you know?

00:28:53:13 - 00:29:01:08
Christopher
And part of it is this idea of overhang that the models are capable of much more ambitious things than we think,

00:29:01:13 - 00:29:01:22
Christopher
because

00:29:01:22 - 00:29:09:00
Christopher
our expectations don't update as quickly as these models have been coming out and they are not getting a little bit better.

00:29:09:00 - 00:29:34:15
Christopher
They are getting, you know, massively better when it comes to information work and synthetic kind of intellectual communications and sort of information management. They're unbelievably good. So that's really the idea is that people see and trust their agent within 24 hours and are getting value within 24 hours. I mean, the next morning that they wake up, all the data is in the system.

00:29:34:17 - 00:29:49:09
Christopher
The agent has reviewed it all. You know, maybe it's taken a ton of notes, maybe it's filled a bunch of data out, spun up subjects, you know, whatever. And, you know, the next morning that you wake up after signing up, you have this kind of revelation.

00:29:49:14 - 00:29:53:11
Christopher
That's that's our time to value. I mean, it really needs to be less than a day.

00:29:53:14 - 00:30:08:09
Christopher
That's amazing. That's incredible. That is. Yeah, highly compelling, especially when you take a look at, you know, other legacy software providers, right, where there's a lot of connection that needs to take place and setup and configuration

00:30:08:12 - 00:30:17:20
Christopher
that might be a bit cumbersome and painful. So that is just there's just such an unlock where you've got this generalized solution where it's conversational.

00:30:17:20 - 00:30:29:05
Christopher
You share as much context as possible. It's not lost or distorted through a form field or whatever it is. And now this agent just starts working for you right away, and it's providing updates

00:30:29:10 - 00:30:31:14
Christopher
whenever you're ready to, to take a look at them

00:30:31:17 - 00:30:36:06
Christopher
in the configuration. To your point is no longer about

00:30:36:10 - 00:30:48:13
Christopher
deciding what clues you're going to want to try to assemble, largely by asking or requiring humans to enter, you know, to fill out dropdowns and forms as they do their work.

00:30:48:14 - 00:31:06:21
Christopher
You know, every time you do a support ticket to fill out these six dropdowns, every time you do a call, you know right up your notes and put them in here and then fill this form out. You know, boy, you better get the right dropdowns in there. I mean, this is a completely different world where the configuration you don't have to do any of that.

00:31:06:21 - 00:31:12:04
Christopher
You can always go back and fill anything you want out automatically.

00:31:12:04 - 00:31:14:06
Christopher
And the things that you can fill out are

00:31:14:06 - 00:31:30:15
Christopher
wildly exciting and on a very strategic level. So the config, in short, is ongoing. I mean, the initial config is minutes, but it's at that business strategy level. You know, it's not. Let me read the help doc on how to make my deal stages by clicking around.

00:31:30:15 - 00:31:39:15
Christopher
And so you don't have to click around. You don't have to worry about that. But what are you doing as a business owner. Like let's talk about that. So it's on on one hand it's harder.

00:31:39:18 - 00:31:54:22
Christopher
You know what I mean? But it's way more valuable. And you walk away from it like, oh my God, I actually have a plan now, you know, as opposed to just trying to click around and get something that looks like, you know, I'm using a CRM.

00:31:54:22 - 00:31:56:14
Christopher
So yeah, that's a lot of fun.

00:31:56:19 - 00:32:07:01

How do you think about, like how professional services might work alongside the technology and the software that you're building? Right. Almost like a forward deploy engineer,

00:32:07:06 - 00:32:22:16

because since there is so much customization and someone getting started, they might not know how to frame the business problem. Or also like what are the opportunities that are available to them? So how do you think about that initial education to get someone thinking much bigger, much more strategically based on what's available to them now?

00:32:22:21 - 00:32:26:02
Christopher
Absolutely. And I know so many, you know,

00:32:26:07 - 00:32:36:08
Christopher
reseller partners of CRMs and all that kind of stuff, and I think in professional services around this, but really around everything,

00:32:36:11 - 00:32:52:21
Christopher
there's one pattern that's emerging. It's like, what do I do in this new world where I used to write marketing content every month for this company, but like, now they can spin up like, I have an agent that just goes to all my meetings, reads all the transcripts,

00:32:52:23 - 00:32:59:15
Christopher
looks at everything I'm riffing on in slack or elsewhere, and then just writes blog posts, just writes LinkedIn posts.

00:32:59:16 - 00:33:00:19
Christopher
I mean, this stuff I

00:33:00:21 - 00:33:03:19
Christopher
don't I don't even have time to read them all, but they're incredible.

00:33:04:00 - 00:33:18:16
Christopher
So if you were that marketing agency, what do you do now? And I think the answer across all this professional services stuff, including sort of CRM implementation partners or anything in sales tech, is again, much more strategic

00:33:18:19 - 00:33:21:17
Christopher
and they can run these agents for you.

00:33:21:18 - 00:33:27:12
Christopher
You will always need some human to be answerable for the work product of AI.

00:33:27:17 - 00:33:31:13
Christopher
There is no company that is succeeding with a

00:33:31:16 - 00:33:33:03
Christopher
work product

00:33:33:05 - 00:33:44:23
Christopher
where where there are pieces of work and it's like, yeah, we don't. No one's really responsible for that. Like, oh my gosh, you have to have some renewable neck for this massively powerful thing you're unleashing.

00:33:45:01 - 00:33:45:18
Christopher
That can.

00:33:45:18 - 00:33:46:09

Be.

00:33:46:11 - 00:33:47:17
Christopher
A service provider.

00:33:47:21 - 00:33:59:05
Christopher
They can come into, you know, your your whatever platform it is, finance, you know, customer stuff, whatever it is, they should be able to come in and say, listen, I can deliver

00:33:59:10 - 00:34:11:13
Christopher
six employees worth of work product for you in answer for it, improve it when you have feedback on it, and I will charge you less than one headcount to do that.

00:34:11:18 - 00:34:16:01
Christopher
I think we're going to see that emerge, and I think it's going to be an amazing business.

00:34:16:04 - 00:34:18:11

That's incredible. Real opportunity for those that are

00:34:18:14 - 00:34:39:10

willing to seize that opportunity, because now it sounds like any industry is up for grabs. I think Toby at Shopify, he mentioned this on a podcast, just stuck with me that in the year of 2026, any industry is up for grabs, but someone that's willing to reimagine it with all the agents and the technology that's available to them.

00:34:39:14 - 00:34:43:14
Christopher
I think that's right. And, you know, to your point, I hope this

00:34:43:19 - 00:34:52:07
Christopher
really gives us what it promises in the optimistic sense, which is the ability to spend more time in fellowship with each other.

00:34:52:07 - 00:34:56:16
Christopher
You know, if we have AI taking notes on a meeting, we can pay more attention.

00:34:56:18 - 00:34:57:01

Yeah.

00:34:57:02 - 00:35:18:12
Christopher
If we have AI reminding us about everything we've promised, we're going to build more trust with our fellow. You know, on the other side of the call, we're going to do more business. We're going to feel better. We're going to get out of work earlier. We're going to miss fewer soccer games and middle school plays. Yeah, I think that's really possible.

00:35:18:12 - 00:35:20:05
Christopher
I'm really rooting for that outcome.

00:35:20:08 - 00:35:20:23

Yeah.

00:35:21:02 - 00:35:35:07

Sounds like yeah I love the optimistic frame there. So Christopher you know where can people go to to learn more. We'll definitely link your LinkedIn and the De website in our show notes. But do you want to direct them anywhere else to learn more?

00:35:35:12 - 00:35:44:23
Christopher
No. Go to date AI and it's self-serve. You can sign up, give it a shot, see if we get you that wow moment in the first 24 hours, and

00:35:45:02 - 00:35:50:04
Christopher
email me if you don't. I'm just my complete first name at AI.

00:35:50:04 - 00:35:52:17
Christopher
Feel free to come say hi. LinkedIn email,

00:35:52:17 - 00:35:54:23
Christopher
come to the website, sign up, anything we can do.

00:35:55:00 - 00:35:55:16
Christopher
We're here.

00:35:55:22 - 00:35:58:11

Love it. All right Christopher, thanks for joining the show.

00:35:58:16 - 00:36:00:04
Christopher
Thanks so much for having me.