How Did This CPO Pull Off 350% Growth in Two Years?!

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Hannah Clark: I heard this great saying recently, “Choose your hard.” The idea behind it is that every decision in life has a challenging outcome, you just have to decide which challenge you’re up for. So for example, being a product manager at a fresh startup is hard, but so is running in circles at a feature factory. Finding product-market fit is really hard, but so is giving up and having to find another job. Then scaling that startup, ugh, talk about hard, that is a ride. But, well, you get it.

So let’s say you’ve decided to go the path of leading product at a startup, finding product-market fit, and then being instrumental in scaling that startup from a 10-person team to a business with a $730 million valuation in five years. Then you might be my guest today, Benjamin Berry, the CPO of EvolutionIQ, which is a company that offers AI-powered solutions for the insurance industry. You’re about to hear the leadership decisions Benjamin deployed to find product-market fit, enable the business to scale sustainably, and then go on to achieve — wait for it — 350% growth over the past two years, despite the volatility of the AI product market and having no insurance background himself. Toward the end of the conversation, he also imparts some of the strategies he used to prioritize and pursue the market opportunities that helped them get there. Let’s jump in.

Welcome back to the Product Manager Podcast. I’m here today with Benjamin Berry. He’s the CPO at EvolutionIQ.

Ben, thank you so much for joining us today.

Benjamin Berry: Hi, it’s a pleasure to be here today, Hannah.

Hannah Clark: So we’ll start it off the way we always do. Can you tell us a little bit about your background and how you got to where you are today?

Benjamin Berry: Sure. I started computer science in college. I was a software engineer in the Boston area for about a decade, moved down to New York with my now wife, and stumbled into product management, which I’ve been doing for about a decade. Six different startups in my career and a couple of, success stories, including I’m really proud of what we’ve done at EvolutionIQ.

Hannah Clark: Yeah, and that’s exactly why I was really excited to have you on today, because we’ll be exploring some leadership strategies in particular that drive successful AI companies, which we, it’s everybody wants to be in AI company right now, but not everyone can do it.

Let’s start off this way. When you joined EvolutionIQ, there were fewer than 10 people. And since then, you guys have gone through some pretty incredible growth. Can you walk us through your approach to establishing a product vision in those early days and how that’s looked as things have progressed in the company?

Benjamin Berry: I would say, as a product leader, it’s a mix of coming in and having a point of view. I had been at another AI company right before working in kind of a subspace, I think it was decision intelligence using artificial intelligence to prioritize decisions. That really allowed me to hit the ground running at EvolutionIQ with a kind of point of view on, how this could work, how this can impact people.

Of course, you’ve got to adapt that to, what’s local to your market. So I didn’t know anything about insurance, so it was really important, especially in those first three months to just drink from the fire hose. Learn everything I could about the insurance world. The beachhead market that we chose, which was disability insurance all the way from, how do they make money to the nitty gritty details of our users, what their day is like every day.

And then, synthesize all of that into a strategy that allows you to accomplish things today, but also, steer towards a long term goal. I think when you’re that early, it’s more important to be strategic than to have a fixed strategy. So much can change when you’re a company that small.

Day to day, week to week that if you get too tied into a strategy, you’ll make bad decisions because you got to constantly be updating it. But you do have to figure out a strategic mindset so that as things happen, you can navigate them quickly and not have to rebuild all your thought process from scratch.

Hannah Clark: Yeah, it makes sense. Yeah. You have that flexible, but strategic sort of mindset.

So you mentioned that product-market fit was really critical in your early success. How did you ensure that the product stayed deeply involved in sales and delivery during this phase? And what impact did that process have?

Benjamin Berry: I think of product-market fit, it’s a definition I heard first from the intercom guys early on, but being able to have a product that you can sell the same way, deliver the same way and get the same results. I think it’s product’s responsibility to be involved in making sure the company can sell your product the same way and deliver it the same way.

And the way that manifested, especially when, there were fewer than 10 people and, most of them were engineers means, I was on sales calls. When you’re fewer than 10 people, you don’t have a sales engineer. So I’m the sales engineer. You don’t have a CS team. So, I’m out there.

With the one of our founders who was doing the selling, like he and I, we’re the CS team. We’re doing the delivery, bringing in the engineers, as it’s appropriate. And so bringing that ethos, not just to the first sale, but over and over to get to the point that you can sell the same way.

That’s when product can step out to get to the point when you can deliver the same way. That’s when product can step out. And if you do that, that means two things. One, product will be helping, implicitly establish the strategies of sales and delivery, but you’re also building trust with those functions so that even if you step away, they’ll come back and pull you in.

Hey, someone is asking for a slightly different value than we usually pitch. What do you think about that? I see a lot of people struggle with that all the time. How do I get sales to bring me into the conversation? Well, if you are providing value to them, they’re going to bring you into the conversation.

So frequently, you’re going to, you’re going to have to tell them no. Right. And so making sure that you’re providing value, to those functions in those functions, which I think is the responsibility, in terms of getting the product-market fit of, great product management, we’ll make sure that you are influencing and tied into those processes.

Hannah Clark: We’re going to get into sort of the meat of the conversation, which is really focusing on the scaling. Because this is, I think, such a really interesting part of your guys trajectory. You guys have scaled so rapidly over the last five years. And I think where a lot of companies, AI or not, really struggle is transitioning from that small team mindset and those kind of scrappy processes into something that’s going to really help the organization to grow sustainably.

So let’s talk about that second phase of bringing on your first team members and Building culture and establishing those processes that would scale with the organization as it grew. What did that look for you at EvolutionIQ?

Benjamin Berry: I can’t say enough about the co founders of EvolutionIQ, but one of them, I would say, very disciplined on the business side.

And so we were always very disciplined in hiring. Which was, great for our cash flows, but at times meant that like we were hiring people sort of just in time, maybe a little later than you might have wanted them. So the first person, I was really bringing in to help me cover, I said, I’m helping in sales, I’m helping in deliveries, I’m, also defining, what an excellent product looks like.

I have a lot of, responsibilities, to the engineering team when that became, 120 percent of my day, it’s Oh, no. I need another person to help here. I think a lot of our scaling was like that was driven by need rather than projecting ahead, which I think is good business.

But that often meant that I didn’t sit down and develop a 12 week detail week by week scaffolding program. And so it meant the biggest part was in the hiring, trying to find people who’d been in a startup culture, you bring in someone who’s not in a startup culture and they’re like, Hey, where’s the onboarding materials?

Right? It’s no. I need you to get on this customer call right now and, bring in people who have worked in B2B before as well. B2B is so much more focused. What I love about it, I feel like you’re so much closer to the users and the customers than B2C, which is almost counterintuitive.

But B2C, you’ve got so many users, you could just sit back and A/B test your way to success almost. So finding people who had that, finding people who are going to be comfortable with data and AI, you talked about AI being the hot thing right now, and it’s very different from building software where I think you can just If I understand the data types, I’m going to have a form.

It’s got some, some small fields, some big text fields. It’s, I need a date here. An AI, if you don’t understand the kind of content, very particularly, people are going to put in that form and then verify that’s going to work. You’re not going to deliver products that succeed. They’re going to look good, in the lab, but when the users are using them day to day, it’s not going to work.

So finding people who have that in the details, in the data mindset, and then bringing them in and really just loading them up with the responsibility. Seeing what they could do and then, To be totally transparent, I think led sometimes a little bit of trial and error. We bring in people who I think were really excellent product managers and didn’t thrive in that context, but brought in some great folks who really did thrive.

And then you can, you can, the sky’s the limit for them, right? Because from day one that you can give them a lot of ambiguity and you just need to give them goals and coaching and they can succeed.

Hannah Clark: I want to talk about some of the more unique challenges around scaling AI businesses, and this is really interesting since we didn’t come from an insurance background before and really had to learn this market from scratch and still managed to succeed in this space.

So in general, I think it’s pretty clear that enterprise focus, like you said, B2B, but especially AI B2B companies, they’re facing unique scaling challenges compared to the B2C landscape. So given all the research that you had to do, all of these kinds of decisions that you had to make, how did you tailor your product organization and approach specifically for this insurance market that you’re serving in the midst of having to learn about it as you go?

Benjamin Berry: Sure. So everyone who joins the team, there’s an expectation that you’re going to be client facing. That’s not a fit for every I’ve met product managers who say, I want to be with the engineer. I want to be in the data, but I’m not really, I don’t want to be out there in the field.

And so everyone’s got to be client facing, especially we’re mostly hiring people who don’t have an insurance background. And so being client facing means that’s how you’re shoulder to shoulder, understanding the challenges and opportunities for our users and our customers. And even AI is fantastic, but the basics of product management are still all about delivering value to those people.

And most of those people today don’t really care if it has AI in it or not, right? So you still have to understand what are their challenges and your opportunities to improve for them and with them. So I think step one is, making sure that everyone in the product org understands that we’re putting the customer first, the user first, that we’re giving them the exposure to the customers and users where when they’re in a room internally and we’re debating something, they’re not just saying, I think this is better.

They’re saying, I just talked to Sarah, over at XYZ insurance carrier. And this problem is crushing her. If we fix this for her, it’s going to change her day. Right. And being able to bring that in. And then we talked about it a little bit, but it’s not just data fluency.

It’s not about, can you get into the SQL and look at it all? But it’s really an urge to both understand the data in aggregate. Okay, we’re seeing these big patterns in the data and being able to ask great questions. Because you can always find an engineer or data scientist. We’ve got a ton of them who can help you answer the questions.

But can you ask the right questions? And then look at when you start to build those answers, can you look at specific examples and confirm that’s working? It’s very easy, I think of when you’re building a machine learning model, what you’re training on kind of very precisely defines the answers that you get.

And if you think about just like going from idea down like a funnel to value, it’s really easy to lose value. In this implementation funnel, if you build Buildy is still building a great model. I can’t tell you the number of times I’ve had, engineering build a model. And it’s look at the precision and recall on this.

It’s fantastic. Look, this is the best model we’ve built. And then you look at the details, and it doesn’t actually solve the customer problem. And you start to untangle why. I’ll give you a great example here. One of our products in disability, unfortunately, some people end up being disabled for a long time.

And the great news is they’ve got insurance. But every year there’s some of those folks Who actually recover enough or circumstances change in the market enough where they could return to work. And so one of our products helps uncover which of those folks, there’s the most opportunity to return to work.

And so you end up training that on claims historically that have resolved where the resolution of the claim means it closes. And you could just take all the claim closures and train your model. And what you’ll inadvertently do is now you’ve got all the people who return to work, but all the people who passed away as well, right?

And if you’re really sick and disabled, that might be more likely. And identifying those people doesn’t help. If your business challenge here is let’s find the people who have the best opportunity to return to work and help them return to work. Finding the people who are actually the sickest and might pass away doesn’t help.

You might build a fantastic model at identifying, that total set. But unless you understand what are all the closures and which ones match the business problem and which ones don’t and making sure you’re only using a positive class that matches your business problem, if you don’t do that work, you just end up losing all the value as you’re building your AI.

So Those are the two things I, I’ve really focused on setting the expectation around capabilities and growth and culture as we scaled the product management team so that everyone could work on, we can move people, again, dynamic, fast moving company, we need to move people around and say, Hey, can you fill in on this product?

It’s growing faster than we thought, everyone needs a kind of pretty broad and flexible skill set.

Hannah Clark: It’s a very sad, but very succinct example of exactly how that works. I’m glad that you mentioned the changing of roles and stuff.

So as you expanded beyond just oversight of product management and you had to pull in things like design and marketing, what are some of the leadership challenges involved with that? As the role expands and you have more oversight, what was that like and how did your role evolve during that transition?

Benjamin Berry: Our product organization includes product management, product design, and product marketing. So I think, a couple of things. One, it’s always, I think, a challenge for any leader once you start to lead people with a job that you didn’t personally do, and that can create, I think, a few different challenges.

I think with product managers, the great news is you’ve got a natural skill set to think about one of the kinds of challenges. Think of these new people as your customer, what’s important to designers, what will help, them thrive understand it in the context of your company.

And then designers have different relationships to their stakeholders and different cross functional stakeholders. So make sure you map that out too and understand what those people need and help your team understand it. I can’t help them necessarily, be a better designer, but I can help them understand what their stakeholders are expecting from them.

What engineering is expecting from them. We did a small company, so sometimes we’re helping marketing now. So let me help you understand what marketing is expecting. That also then speaks to either don’t enter it thinking I’ve got to be the best product designer to help them. You’re a leader and you have that expertise, but don’t overstep your expertise in their domain.

So, I always try to be, when I’m giving feedback to designers, I always try to think, Hey, I was hoping the product would feel like this or create this reaction, right? Cause I can be an expert on that and then leave it to them to figure out. Great. Here’s the revision. It’s not that I don’t have any ideas.

Maybe there should be a radio button instead of a dropdown. It’s just that, they don’t need me to do that as we grew the design team. It’s important then to bring in someone who can lead the team in that way and is an expert, in, in that domain and can lead and grow people. But as you hire the first person, I think you want to set them up for success.

Again, think about helping. Map out their customers, help them understand that, and then figure out how you can coach them without trying to push knowledge of that domain on top of them. The other thing that’s important is to understand why does it make sense to have these people in your team, right?

Of course, it’s always flattering to grow your team. And so I think product design is maybe a little bit more obvious, but product marketing, the fewer customers you have, right, naturally means those customers are going to be higher values, right? Higher ACVs. That also means longer sales cycles, a lot more time past the awareness stage of the funnel and into the stages of the funnel where, they’re considering your product and you’re making sure they understand.

And that means your marketing aggregate is going to lean a lot more on product expertise and the ability to, inform the market that you deeply understand their problems and that you have a product that helps, with their problems, also dealing with more stakeholders. This just ends up being more translation of your value propositions to different folks.

And so that leans a lot more to, Hey, instead of having product marketing really tied in, they’re going to bridge this regardless, but you know, the dial could turn way towards our product marketing is really focused on our brand. So it’s really focused on our product expertise. And yeah, I think the closer you go to smaller customer base in this bigger enterprise deals, the more you’re leaning on product expertise.

And so that means better to have them in the tents with the product managers working on the value propositions and deal with kind of the friction between them and marketing. Then the other way around, I think it was a B2C company, I would say, Hey, don’t put product marketing, in here with product management.

Like they should be really focused on the brand and how that’s the awareness stages of the funnel. And we can teach them about the products, we owe them that, but like that’s where, most of their work’s gonna be, having a point of view. What belongs in your org and why, and that’s going to be local to your company.

It doesn’t work the same everywhere. And then we talked a bit about coaching and setting up teams that aren’t, from your background for success.

Hannah Clark: I would really like to dive in into that developing leaders thing. You touched on a little bit about developing people into leadership positions, because you really need that in order to grow and scale effectively, no matter what business you’re in.

So what’s been your experience finding and developing leaders within the organization or external to the organization? And how did you figure out who could take ownership of different product functions and what was the best development path to put them on?

Benjamin Berry: I think every leader is so shaped by their environment.

And I think for me, just coming up, I’d seen so many times where people really grew within an organization. And then, the organization, it can be hard to see that, I think, right? Because it’s easy to think about people the day you hire them and forget they’ve grown, three, four years. And then now you bring in someone over them because we need more leadership.

And then that person leaves and you end up with a leader who’s maybe shaky. They’re, they might be great, but they’re new to this context. Right. And will that work out and you’ve lost, your best people, and so I always try to really think about, can I grow someone internally into a leader? Again, that’s probably just the reaction to my environment, but in terms of how do you do that, I am a very, I would say I’m a pretty hands off leader, right? So I try to, I tell people I’m always willing to spend all day talking to you, coaching you, working through a problem with you, but I’m not going to come knock on your door and be like, Hey, walk me through, every step of all the details of what you’re doing.

I’m happy to do that, but I’m not going to micromanage what you’re doing. And so, that makes it actually, in some ways really easy to figure out, who can grow, right? Because you give them some responsibility and they crush it. And so people might struggle with that ambiguity. And then you give them, something bigger and something bigger.

There’s a gentleman that, on my team, Matt Gillespie, we just promoted him to VP. And he joined as senior, technical product manager, right? And he’s climbing the ladder quickly as the company has grown and it’s been, every step of the way, as we’ve given him a little more opportunity, he’s knocked that out of the park and it’s great, let’s give him the next stage of opportunity.

And that always helps me because then every time I’m doing that, I’m taking something off my plate and letting me, focus on, one other thing. And so that’s I know that was pretty broad. So feel free to ask me for more specifics, but that’s my answer.

Hannah Clark: I mean, broad is good because we, not everyone’s going to be in this niche. It’s it’s always great to be able to transpose what your leadership advice is and development advice to what our individual situation is. So broad is good.

I’d like to actually switch gears just a little bit and talk a little bit about product strategy and market selection. So how has your approach to identifying and prioritizing market opportunities contributed to the growth of EvolutionIQ over the years?

Benjamin Berry: Think about it maybe at two levels. So we, when the company was founded, the focus was bringing AI to insurance, talked to, this was a little bit before I joined, but I know that they talked to a lot of different people and found, a first ideal customer within disability insurance and then followed the playbook that, if you crossing the castle, if you read that book, right, hey, obviously, vision wise, Tam wise going to pitch to a VC, let’s talk about the impact AI can have about claims handling and insurance, trillions of dollars in the U.S. alone, right, and we get to a pretty big time pretty quick, but you can’t, actually function that way.

So we drill down into disability insurance and, that was our focus until it became clear we were going to be the dominant players with, AI claims guidance and disability insurance, and then set the horizon bigger. In terms of how do you pick then the next horizon, we looked at a lot of different, adjacencies. You could take AI to other parts of the insurance. Are we focused on claims, but there’s selling insurance underwriting. So that’s one degree away. I’m still selling to the same person or same organization, but into a different function.

Or you could take what we’re doing in disability. What drives those claims is bodily injury. Okay, let’s take AI bodily injury. Are there other claims like that? Yeah, there are over in workers compensation insurance, right? And so those are just two different degrees of freedom. So we mapped out a ton of different opportunities, and then we looked at everything that was one degree of freedom away, thought about what are the pros and cons of making that switch, right?

Staying within the same order, great, I get to use the same MSA for contracting, but now I’ve got a whole different set of logos I’m potentially competing against. I’m walking into a problem set that I don’t know anything about, right. And these are, deeply, expert, users. So that’s pros and cons.

And then we looked at what were the sizes of those, and then you just spreadsheet out some math and you’re like, Oh, we think these are the best ones, but the proof is in the pudding. You’ve got to then go out and start having those conversations and validate that, all of your assumptions are right.

And that the hypotheses did. So that’s like the macro of kind of market selection. I think in the micro, we trying to map out all the challenges and opportunities we think exist for our users and then build, for insurance claims come in and they go through almost a funnel, like there are fewer claims over time and they go through these stages and different things are happening.

So making a just an abstract map of those stages and understanding how much value there is and claims tend to cost more over time as well. So how much of that development happens in this stage versus that stage? And then thinking about my solutions and how do they map onto that helps you size what you think all your solutions are and then just picking the highest value ones, which isn’t always, then you’ve got to go back to your customers and validate that you can sell that to them.

It’s interesting because if you just go to them first and you’re like, Oh, I’m being customer driven, the challenges that are top of mind are often not the most valuable challenges. But then when you come back to them and you’re trying to pitch them, these are most valuable challenges.

Sometimes you might have to give them a little bit of what they want. Okay, I know these, this broccoli is the most valuable for you, but I got a little cheddar cheese on top of it to get you to eat it, and so that’s at a more tactical level, how I think about growing within a market.

Hannah Clark: As a toddler mom, I appreciate the broccoli and cheddar cheese.

Just to wrap things up here, cause I know that it’s a kind of a broad question to talk about the most successful leadership decisions that you’ve made, but I think that it would be really good to drill down if you could really think about some of the most important leadership decisions that have differentiated the growth journey that you guys have had at EvolutionIQ over others when so many AI companies are really struggling to scale successfully and sustainably.

What would you credit as being your most important decisions As you think back at the last few years?

Benjamin Berry: One, even though AI is exciting, it’s always, keep the customer first and understand the market and react to that. I mean, that’s the basics of product management. And that’ll always be true. On the AI side, understanding that, this is a paradigm shift and it’s not just, Hey, are there new AI tools?

I can use ChatPRD or chat, all these exciting things that, that I might use, but think about how developing AI products is going to be different. Like what that changes about what your product managers need to do and your engineers need to do. And that’s what the handoffs are between them.

The same thing for design. I’m asking my designers to build something that’s not deterministic. Now it’s stochastic and the expectations of users are different. So I need to make sure I’m bringing in designers that can do that. The thing is, because it’s so new, because of this paradigm shift, there really aren’t a great set of tools where I, if you’re in 2015 and you’re building a SaaS, workflow product, there’s 15 years of great templates and tools, and you can go by the numbers a little bit.

And here, there’s a brand new space and you’ve got to be willing to think about that and map that out to drive success. And then the last thing in all these decisions is let the context of your business come to you. I would say, I, you asked me a lot of questions about scaling and I talked a lot about product emphasis and, giving people a lot of freedom as a result.

On an abstract level, I would love for the standard to be higher. But when I play back, you know why it isn’t, it’s because when I brought people in, my focus, with them was be in front of the user, help sales, help delivery. That’s a lot to put on someone’s plate. And then also be sure, why aren’t your PRDs perfect?

I’m not spending 40 hours a week on them, right? That person teaches the next person and on, right? And so now that we are at scale, we can go back and kind of work on these things and make everything be really polished. But it would have been, I think, a mistake to go back three years ago and say, we got to drop everything and make sure all these PRDs are our top shelf.

Nothing didn’t have any challenges, but you know, I, instead of doing that, we were doing things that were helping us grow the business every day. And that was important for our business, but that’d be different for another business with a different customer base, even within enterprise B2B, you could be selling to franchises, right?

And you’ve got tens of thousands of potential customers and what you’re doing is just very different. And so making sure that you don’t just apply, the lessons you learned at the last place or you learned at the last conference, but you really think about which of those lessons are appropriate for the context that I’m in here, the company I have, the talent that I have, the market that I’m in, that I think is the biggest thing and it’s, what I love about EvolutionIQ is it’s not just me. I think all of the leadership, in engineering, in sales, I think we’ve all been really flexible in that way. And that’s been the biggest driver to succeeding quickly is, always adapting to, I like sports, right? So if you think about you’re playing basketball, I like LeBron James and he just, he’s a fantastic player and he just had Luka Dončić joined his team.

He changed how he played. And I think that’s what makes him really great, right? Is he could have just said, Luka, you’ve got to fit into my system, but he said, no. For me to get the most out of Luka, I’ve got to fit in. I’m going to change my game to work around him. And now the Lakers are doing amazing.

There’s a lot of things, very complicated, a lot more into it than that. But you know, LeBron’s ability to adapt to what the situation is, I think is what’s made him be an all time great, with an incredibly successful 20 year career that will allow you to be successful in any context.

Hannah Clark: Thank you. That was a very beautiful example. I was a little nervous when you switched from sports from broccoli cheese because I’m much more familiar with the broccoli cheese situation, but the LeBron James story is definitely that’s a really cool way of putting it.

Thank you so much for joining us, Benjamin. Where can people connect with you online?

Benjamin Berry: You can find me on LinkedIn. It’s probably the best way to find me. It’s just Benjamin Berry. I will respond to messages there. I’m sure I’m on other socials, but that’s where I spend the most time.

Hannah Clark: Sounds great. Well, thank you so much for making time today.

Benjamin Berry: Thanks, Hannah. Have a great weekend.

Hannah Clark: Thanks for listening in. For more great insights, how-to guides, and tool reviews, subscribe to our newsletter at theproductmanager.com/subscribe. You can hear more conversations like this by subscribing to The CPO Club wherever you get your podcasts.