Making Sense of Martech

"The secret is you don't let the old man in." - Sam Allen, quoting Clint Eastwood

In his first official interview as CEO of Iterable, Sam Allen joins host Jacqueline Freedman for an unfiltered conversation on leadership, AI, and the future of marketing technology.

Drawing on lessons from the Marine Corps and Salesforce, Sam shares his philosophy of servant leadership, why AI should act as a marketer's co-pilot, and how companies can move beyond "vendor" status to become trusted advisors. He also reveals his strategic vision for Iterable's future and what CMOs must do to stay relevant in today's fast-changing Martech landscape.

If you're a marketing leader navigating AI disruption, growth, or organizational change, this episode is for you.

Highlights

  • How servant leadership and radical transparency build resilient teams.

  • Why AI should empower marketers as a co-pilot, not a replacement.

  • The strategic vision behind Sam Allen's move to Iterable.

  • How to win the AI talent war by prioritizing culture.

  • Practical steps to strengthen marketing and sales alignment.

  • Why Martech stack consolidation is key for long-term growth.

Timestamps

  • 00:00 – Introduction & Guest Welcome

  • 00:43 – Rapid Fire Questions

  • 03:42 – Leadership & Personal Insights from the Marine Corps

  • 05:33 – Transition to CEO of Iterable

  • 09:24 – AI & Innovation at Iterable (Nova)

  • 14:11 – Ethics & the AI Talent War

  • 18:04 – Moving Beyond Vendor Status with Customer Relationships

  • 20:02 – Navigating Budget Constraints

  • 21:07 – Standing Out in a Competitive Market

  • 22:33 – Personal Insights & Martial Arts

  • 23:04 – The Future of Marketing Technology

  • 25:13 – Ethical Considerations in AI

  • 32:31 – Advice for CMOs & Marketing Leaders

  • 37:23 – Podcast Recommendations & Closing Remarks

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Creators and Guests

Host
Jacqueline Freedman

What is Making Sense of Martech?

Unfiltered takes on the biggest shifts in marketing technology. We spotlight what matters, who's leading (or lagging), and what's next. In Martech, clarity is power — and we're here to deliver it.

jacqueline: Welcome to the Making Sense of MarTech podcast, where we interview leaders and put them. In the hot seat. I'm Jacqueline Friedman, founder of Monarch and Global Head of Advisory for the MarTech Weekly. Let's dive in and meet for the very first time. Sam Allen, the new Chief Executive Officer at Iterable.

jacqueline: Okay. And also I hear you're a dog person. Name your favorite breed.

sam: I won't tell you who it was with, but I saw someone who ran a very big field marketing division want to send, I think it was about a thousand boxes. As an a BM, you know, account-based marketing campaign. And it struck me as very dated and it was not cheap to do that. It was all sent FedEx overnight bespoke to executives.

And that was not an easy thing to do. And she's still amazingly at 87 and great, great spirits and great health professionally. And this may come off a little bit different, but. I've always really admired is Clean Eastwood, primarily because, you know, he is in his mid nineties and he is still incredibly active and there's an interesting side note.

sam: Well, so the most important thing is you always put your people first. You know, there there's a term now, it's been banded about the last few years called servant leadership, but that's really the biggest lesson for me learned in the Marine Corps is that you come last.

sam: it comes to, well, one more thing by, by the way, uh, just to add there is, you know, the Marine Corps is, it's a lot of things and there's a lot of. Assumptions about it. But I will tell you it, it is a very direct world and I have found that people constantly crave transparency in leadership.

sam: Yeah, so it's a combination of things. Iterable itself is an amazing company. It's one I've admired from afar for a while. I think their innovation is stellar. You know, we live in a world where specific technologies aside.

It's an absolutely amazing company. I love my time there. Mark Benioff is a true genius and I, I take a lot of what I learned and I wanna apply that here. But from a personal growth perspective. It felt like it was really time for me to go do something else. I had gotten a long way in that company, done a lot of amazing things, but I felt like it was time for me to jump into a CEO seat myself and take full responsibility and, and grab the reins.

jacqueline: Understood. And even though you didn. Say anything bad, I'm just gonna go ahead and say you chose Next Gen Tech over legacy tech, so maybe Marketing Cloud deserves a little bit of a a Yeah. Little something there, but, and I'd be remiss if I didn't bring up that herbal as experience. Several very public leadership changes over the past number of years.

And there was a lot for us to go accomplish. We have an amazing team to go do that. And so for me it's, yes, I wanna understand where this company has been because it's gonna help me refine the journey forward, but make mistake. I am here to drive growth in this company and I'm very excited to do that.

It's working code. He goes, there is some, you know, some UX design stuff we did at the front to make it more easy to share with a crowd. But he said, this is a, this is a working code and this is something that, you know, we're gonna be rolling out, you know, in stages in the very near future. And so for me that was incredibly, incredibly compelling and I was, uh, just tremendously excited about that.

That is my responsibility. Set the plan, drive the plan, drive accountability, drive performance, make sure we take care of our people, take care of our customers, evolve the brand, and evolve the values in the company. We can talk about that in a minute if you like. But I'm also very cognizant of I'm new.

jacqueline: I agree, and you kind of alluded to it, but with the latest waves of AI innovation in general for the MarTech industry, they've all really been point and shoot. Solutions. It's, you know, one singular thing versus I've seen the demos of Nova. I'm glad to know it wasn't all Figma. Um, it's a complete and total overhaul of the interface, and I think we are entering into the new AI landscape that is all interface based who's going to be that winner.

And the way that you do that is you deliver amazing top line results in an efficient manner without asking for a bunch of resources to do that. And so what Nova is doing is creating. AI capabilities and agent that are gonna allow those campaign managers to drive those bespoke personalized, uh, campaigns and events with users and prospects that make those users and prospects feel like, as I mentioned earlier, that they're the only customer.

And so you think about that in construct of marketing technology. How do you grow your user base, grow your engagement without asking for a bunch of more capital? And the way you do that is through an advanced technology like Nova.

We have to present them as a partner. How they should be thinking about the capability, not just the capabilities of AI and what the art of the possible is, but how actually that will make them better. And then we need to have very strong feedback mechanisms and feedback loops with our customers so that when there are challenges with AI and we haven't seen it yet on our side, but they may occur that we jump on top of those, um, we're committed to making sure that our solutions and our capabilities are best in class and best in breed.

jacqueline: I love the sound of that and also kind of maybe where values come into play with this next question. Mm-hmm. Work. In the midst of an AI talent war, you read any headline and you're seeing some crazy numbers, crazy things. Mm-hmm. From a leadership strategy or philosophy for maintaining top talent is, to your point, those core values, those ethics top of mind, or how are you navigating this greater?

You know, I kind of question someone who's just gonna jump. Ship to ship these huge pay packages. How are you impacting the customer experience by doing that? Are you putting the customer first? Are you putting your team first? You putting your people first? The answer to all those things is no. You're putting yourself first.

What are other top reasons folks should be leveraging certain frameworks as they evaluate and prioritize which vendors should send best?

And so I think the companies that are gonna long-term win and, and perform the best are ones that have that mindset. And every time I've walked into a sales cycle. And sometimes this is to the chagrin of our own salespeople. I'll say, I'm not here to sell you anything. I'm here here to make sure that you feel supported to the customer and that we are building a long-term relationship with one another.

jacqueline: Agreed. I think thinking about. The entire market as partners and that partner ecosystem you build for your team is far more important than a point and shoot, we chose this vendor because it solves X and y. Yeah. That the fabric in which you choose for different partners and platforms.

jacqueline: I agree with you, and I also will push back. I don't think any vendor decisions should be made from the top down. It should always be from the ground up. But I do understand the sentiment and the thought.

You know, we are architected from the ground up to be an AI centric company. Many of those people you mentioned are not AI is either a Bolton or an acquisition. They have to figure out how to integrate. They have distributed architectures where data residency, storage, compute, queuing are in different.

sam: Used to, and my knees were kind of shot, but Yeah.

And so what we have an opportunity to do is come up with that kind of answer, like, where do we think this is gonna be in two years? I don't have a specific answer. I will tell you this, the move to make marketing a core high value component of every business in terms of, Hey, this organization is really driving our top line, is gonna be key to what we provide.

jacqueline: And there's some former coworkers of yours at all of these different.

He's no longer with us. And he wrote the book in 1982, and there's a section in the book where he is talking about how he's walking through this stenographer pool to go to the mail room. This country used to have tens of thousands of stenographers that, and if you ask people under the age of 40, they probably know what a stenographer even is, right?

You know, prompts for business planning. And so that's a job that didn't exist before. And so that's just my soy. I don't know how I think about it. To answer your question more specifically, the way I wanna present this to customers is, look, we're gonna provide you the capability with our AI field solutions to drive amazing results.

Are constantly pushing the envelope and seeing how far we can go. So that's why I think the ethical use stuff is so important to kind of keep us grounded a little bit. And you, you know, you made a comment earlier about decision making and people in the trenches. I'm not sure what term you use, but I agree with that.

jacqueline: No, that makes sense. It also reminds me of those who dictate and would hand it off to someone to type it up. Well, taking a larger step back, we have over 15,000 MarTech vendors according to Scott Brinker and his annual report. If you were to predict, how do you think CMO should be rethinking. Their marketing tech stack orchestration and also with my own personal bias of they should be thinking about it, but of course looking to their team to work on it.

As an example, then you can start to split manufacturing and do different things there. And so I think that's a reason why there are so many. I do believe it's a sector that does need consolidation. It's too confusing for customers. Again, that's why the advisory partner piece is so important. It's on a near impossible place to be all things to all people, and so you're always going to have.

And so I wanna be able to go to an enterprise CMO as an advisor and say, Hey, here are the five components of your marketing tech stack that you absolutely need to have above and beyond Iterable. And so it's important to me to become an expert. In that sector. Sector, I know a little bit enough to be dangerous, but I need to become much more expert.

sam: well. Well, I just one comment on that. Somewhere in the neighborhood of 60 m and a transactions under my belt between Salesforce and Cisco systems, and Cisco was a bellwether for how you do this. And when I was at Cisco, we did deep integration very fast. And it's interesting to me, and we did it, the latter ones we did at Salesforce, you build a model for an acquisition that you have to pitch to your m and a board.

Yeah. Consistent challenge. I'll be biased and say it's definitely gendered in a, in some regards, and the marketing, everyone thinks they can do marketing versus everyone knows they can't be a full stack engineer unless they are one. And so I'm curious, what advice do you have to give to senior leaders who are really advocating for their teams but maybe not succeeding?

It's like, well. I need to draw a top of funnel and build awareness, and here's what we think, but it's not definitive and it's multi-variate, and I need a way to build a weighted average and people's eyes start to roll back in their head. But that's the truth of it. And so my advice for CMOs is to understand that perception and create a story that solves that.

I think they are peers at minimum.

I need a bunch of bespoke dinners where I can get 12 CIOs of banks in a room to talk to one another. And maybe we have, you know, an Olympian or a famous author or someone come and, and be part of the conversation that's 10 times more valuable than a strategic event. And so the marketing team did that for him because they listened and they didn't think, oh, it's better for me.

But will we ever be in a perfectly friction-free environ? No, that's just part of human nature. But I think, so to round back to your question, you know, providing a marketer the ability to go and say, look, I drove that growth and I did that efficiently, is the fastest way to get real power at the C-Suite table,

You know, CMO knows it all, but. Really has a really strong bent there, uh, and a great leader and a great person. I think those are three just phenomenal leaders that you should have, and I'm happy to help make intros if that's needed.