It’s been an exciting year at Iterable, and one of the biggest moments so far has been welcoming our new CEO, Sam Allen.
This past week marked Sam’s first full week in the CEO seat, and we wanted to hear directly from him while the impressions, insights, and energy are fresh. First weeks are often a blur, but they’re also when leaders see things with the clearest eyes: the people, the culture, the opportunities, and the challenges that will define the road ahead.
I sat down with Sam to reflect on his first week and how it’s already shaping his vision for what’s ahead at Iterable. His answers are open, thoughtful, and full of excitement for the journey we’re on together. Let’s jump in!
1. How would you describe your first week in three words?
Energizing. Innovative. Opportunity.
2. What’s one question you asked in every meeting this week?
“What’s getting in your way?”
It is straight to the point, and it tells me two things fast: where we have friction that’s slowing us down, and whether we have the tools, information, and support to move forward. My job is to clear obstacles so the team can execute at full speed. I’m not interested in perfect solutions that take forever. I want directionally accurate answers, quick decisions, and progress at pace. Asking this question in every meeting gives me a real-time map of where we can act now to make that happen.
3. Was there anything that surprised you about the team?
I expected talent. I expected drive. But what has surprised me is the genuine alignment between people’s personal values and Iterable’s mission. That alignment creates trust—and trust is the foundation for speed and innovation. It’s rare to find a team that’s this willing to be transparent about both opportunities and shortcomings. That level of honesty tells me we’re ready to build something exceptional together.
4. What’s the first thing you noticed that Iterable does differently than other businesses?
We don’t just talk about the customer; we build from their perspective outward. That sounds obvious, but in most of the tech world, the gravitational pull is toward the product roadmap, not the customer’s reality. Iterable’s DNA is customer-centric in a way that allows us to design for their outcomes, not just our feature releases. That’s how you create partnerships that last.
5. What would you tell a friend if they asked, “So, what’s special about this place?”
Iterable is a place where ambition meets humility. The ambition to lead in our category. The humility to listen to the customer before we make our next move. And the discipline to execute with precision. We have the agility of a startup, the reach of an enterprise platform, and a culture that values people as much as performance. That combination is rare, and it’s worth protecting.
6. What’s one thing Iterable will do in the next year that will surprise the market?
Iterable Nova, the new marketing AI agent our team announced at Activate Summit this past year, is going to blow the market away. The market expects AI to save time. We are going to prove it can elevate creativity, sharpen personalization, and make customer engagement feel more human, not less. Nova will redefine what it feels like to create and receive marketing, and it will change the conversation about what AI in this industry can do.
7. What’s one lesson from the Marine Corps that applies directly to leading at Iterable?
In the Marines, you need to trust the person next to you, and that trust is inviolate. You also need to approach your challenges with a diverse set of skills that are applied with fluidity because in the fog of combat, changes happen immediately and chaotically. This is why discipline matters, as does the reliance on those around you to be expert at their craft.
That lesson applies directly to Iterable. The challenges we are solving for our customers require creativity, adaptability, and trust, and those come from building teams that reflect a wide range of skills and experiences. We are building a team that brings different strengths to the table, challenges each other respectfully, and shares the same commitment to the mission.
8. If I could ask every customer one question, it would be…
“If we could deliver one outcome in the next 6-12 months that would meaningfully change your business, what would it be?”
That question cuts through feature requests and wish lists. It forces both of us to focus on what will actually move the needle, and it turns the conversation from short-term sale to long-term partnership and value.
9. This was Week 1… what do you want Week 52 to look like?
By this time next year, I want Iterable to be the company everyone talks about. Not just because of what we built, but because of how we built it. I want us to be recognized as the most innovative team in the industry, where ideas turn into action faster than anyone thought possible. I want Iterable to be the best place to grow, where people feel trusted to do their best work and proud to see the impact it makes. And I want to be the partner every brand hopes to work with because they know we will help them win. If we do that, it will not just be a good year, it will be the year we set a standard the market can’t ignore.
10. What’s one moment from this week you’ll remember a year from now?
My first Town Hall. It was the first time I had the entire Iterable team in one forum—every office, every time zone, all showing up together. We opened with a question, ran through the wins from the last quarter, and what hit me was that every single highlight was a cross-team victory.
In the chat, people were shouting each other out, calling attention to teammates in other departments and other countries who had made the success possible. For a virtual meeting, the energy was electric. You could feel the pride, not in individual accomplishments, but in what we built together. For me, that was the moment I saw how much this team values collaboration—and how powerful that is when everyone is pulling in the same direction.
The Road Ahead
It’s only been a week, but Sam is already diving in with a clear vision for what’s next. There’s a spark of fresh energy in the air, and plenty of big ideas brewing. If this is just the first chapter, we can’t wait to see what’s next!
For more leadership from Sam, follow him on X!
