Growing as a CPO as your product grows from 0 to $10B valuation | Tomer London, Co-founder and Chief Product Officer at Gusto | E235

In this episode, of The Product Podcast, we chat with Tomer London,Co-founder and Chief Product Officer of Gusto, the leading HR platform for small and medium-sized businesses in the US.

Tomer shares his journey from coding his first inventory management system for his dad’s clothing store as a teenager to building Gusto into a comprehensive payroll and HR platform serving over 300,000 small businesses. He opens up about the challenges of evolving his role as CPO, transitioning from hands-on coding to building product teams, and scaling the company while staying deeply customer-focused.

In this episode, Tomer dives into the importance of embedding compliance into the core of Gusto’s product, why he believes product management should be data-aware but not data-dependent, and how he fosters a culture of intuition-driven decision-making. He also shares how Gusto integrates AI to streamline processes, from payroll automation to enhancing customer support, all while maintaining the human touch that defines their success.

CONTENT
(00:19) 🌱 Early Beginnings: Building Software for a Small Business
(03:33) 💪🏽 From Engineer to Product Leader
(04:45) 👨🏽‍⚖️ The Importance of Compliance in Small Business Solutions
(11:00) ⚖️ Balancing Data and Intuition in Product Management
(20:26) 💥 Gusto's Product Expansion Strategy
(35:51) 🤖 AI and Human Touch in Customer Experience

KEY TAKEAWAYS👇:
Customer-Centric Product Development: Tomer emphasizes that listening to customers and addressing their pain points is the foundation for building successful products. Gusto's focus on helping small businesses manage compliance and payroll seamlessly has driven its product-market fit.

Data-Aware, Not Data-Dependent: Tomer believes that while data is important, product managers should balance it with intuition built from direct customer interactions. This approach ensures that products are not just functional but deeply aligned with user needs.

Scaling with AI & Human Touch: Gusto’s innovative use of AI enhances internal efficiency and customer service. Tomer shares how AI-driven features like automated data entry make life easier for users, while maintaining personal connections through exceptional customer support.

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CREDITS:
Host: Carlos Gonzalez de Villaumbrosia
Guest: Tomer London

Transcript

(00:00) Carlos 
Welcome to the show, Tomer.

(00:00) Tomer London 
Alright, thank you, thank you. Great to be here.

(00:00) Carlos 
I heard that you built your first software for your dad's clothing store?

(00:06) Tomer London 
Yeah, exactly. When I was, so I grew up in Israel, and my dad has a small business, a clothing store that he's been running now for over 30 years. And I just grew up like many small business families, just going to the store almost every day after school and helping, you know, whether it’s organizing or cleaning or answering phone calls or whatever needed to be done. And at one point, I figured out that—or I learned—our inventory is just such a messy process to go and track all the inventory, what we have, what we don’t have, what we need to order from vendors, and so forth. So I was lucky enough to be introduced to Visual Basic 6. I got this wonderful book from the bookstore right next to it and learned how to code and build a very, very simple inventory management using Visual Basic 6. And that's really the first software I built that was useful. And I got to see my dad using it to run the business. That was just a huge moment for me—just building something that helps people, you know?

(01:15) Carlos 
What age was that?

(01:21) Tomer London 
I want to say like 14, 13—something like that. And, you know, growing up in Israel, my native tongue is Hebrew, so I was just really lucky that that book was available and translated into Hebrew, so I could actually learn and go code it on my PC back home. Probably a Pentium.

(01:47) Carlos 
That's awesome. Well, you started adding value early in your life. Another fun fact I see is that you play the guitar and drums.

(01:50) Tomer London 
Yeah. Yeah, I love that. I love that. My life is like, you know...

(01:58) Carlos 
There are a lot of engineers and product people who are into music. Go ahead, please.

(02:02) Tomer London 
Yeah, my life is like building Gusto, family and kids, and then music. In my free time, I drum and play guitar.

(02:14) Carlos 
I’ve seen a lot of engineers who are really good at music, and there must be a strong connection between coding and also coding music in a way.

(02:25) Tomer London 
You know, for me, when I play the drums, it’s almost like certain parts of my brain get turned on that aren’t on throughout the day. There's an incredible amount of blood and energy flowing to that side of the brain, and you get to be extremely present, in the moment, and just not think about anything else—not worry about anything. You're not interrupted by random thoughts. You really focus on the rhythm and getting it right, and it’s almost therapeutic.

(03:00) Carlos 
Well, let’s talk about Gusto and your own evolution as the co-founder and CPO. You’ve kept the same title, but I can imagine your job description or responsibilities evolved quite a bit. I’d love for you to guide me through that journey.

(03:14) Tomer London 
Yeah. When we started the company—this is late 2011, early 2012—it was just the three of us: Josh, Eddie, and I. So there was no product to be a CPO of, you know? There’s no product to manage. It was just the three of us. So, in the early days, the three of us were coding. We went through multiple different chapters, maybe four or five, six different chapters throughout my 12 years at the company, and each chapter has its own meaning for me in terms of what my role was, how it evolved, and what I was focused on.
I would say the first chapter was from when we started the company, just the three of us, until we had probably around 12 engineers, something like that. And throughout that time, my focus was coding. I was writing software just like the next engineer. And in my non-coding time, I was writing specs and figuring out, given the customer conversations we were having—or I was having—what needed to be built. So that’s the first chapter: coding, talking with customers, writing specs.
Over time, starting with just the three of us, I was coding 90%, 95% of the time. Then, when we got to around 10 engineers, I’d say it was more like 10% coding at that point. Also, over time, I realized that the team needed me more and more to focus on specifications—bringing in customer insights, understanding what customers were telling us, their feedback, their biggest problems—rather than coding.
Another thing I was responsible for around that time was our customer care and compliance teams, which is very important in our business because, when you think about payroll, our initial focus was just helping small businesses with payroll. The goal was to eventually expand, and that's what we've done—expanded to offer a platform for everything a small business needs to start, build, and grow their teams in a compliant way.
We started with payroll, and payroll is all about maintaining compliance—making sure you don’t break the law, that you work with the IRS and state agencies correctly, and that you comply with the hundreds of thousands of rules and regulations using our software. For me, as the Chief Product Officer, this was really important. You have the compliance side and the software building side.

(09:08) Carlos 
So what’s it like now?

(09:21) Tomer London 
And now it's all about, with this really large scale, I’m going to be focusing specifically on emerging products, the things that are newer, more zero-to-one, kind of higher risk. And that's kind of what my job is today.

(09:42) Carlos 
One of the things that I love about what you said is how you're redefining your own job description to also focus on where you can add the most value, instead of what the book says you should do. You know, like, yes, there are probably better managers or specialists in different areas, but you find those areas where you can still be in your genius zone and add tons of value while keeping an eye on other things that aren’t just product-related, right? You mentioned compliance, you mentioned customer success. I've seen more and more companies including those functions under the product umbrella because it makes sense, right? It’s not just the technology piece. It’s also about what your users are doing with your product and how you can ensure there’s a connection to improve it.

(10:42) Tomer London 
Right. Exactly. Exactly. And I would say product management, in my opinion—and maybe this is controversial—product management is made up. If you look 100 years ago, there weren’t universities teaching product management, right? A lot of jobs have thousands of years of history, but product management is not one of them. What I mean by that is, it really depends on the specific company, the specific product, the specific business. The practice and craft of product management should be tailored to what you’re trying to do with that business and those customers.

(11:08) Carlos 
Yeah, and applying that same mindset to the reason behind your company and why it exists. I'm curious to know why you picked compliance or payroll, because that resonates with something relatively unsexy.

(11:23) Tomer London 
Yeah. Well, you don’t think compliance is sexy? For us and for me, the passion is around small businesses and entrepreneurs. The passion is: how do we help more people start companies, hire teams, and make those teams successful, right? That’s the focus. Imagine a world where it’s easier to start a small business, hire a team, and build a team that does great work together. That unleashes an incredible amount of creativity, productivity, and opportunity. That’s a world we all want to live in, and that's where we're coming from. Now, the government creates—and you won’t believe this—15,000 new rules and regulations every year for businesses. 15,000! Just reading all the rules would take your whole year, right? So that’s insane. Again, it comes from a good place—these rules are to protect consumers and businesses—but the result is that it becomes really hard to comply with all of them. What we’re trying to do is make it really easy for businesses by automating all these compliance requirements, whether you’re a small bakery with three employees or a 200-person tech company across the US and the world. We want to make it as simple as clicking a button in a computer game, where you just hire someone, and everything gets done so that people can focus on building their business.

(13:23) Carlos 
I’m a big fan of so-called "unsexy" businesses—picking a niche where not a lot of people are looking—and you mentioned that customers are frustrated, right? They’re upset with the current state of things.

(13:38) Tomer London 
Yeah, here’s a story I’ve got to tell you. There’s a competitor—I’m not going to name them, let’s just call them ABC. One of the things we did early in the company, before writing a single line of code, was just going around talking with a bunch of potential customers—literally anyone who would speak with us. Friends, friends of friends, professors—I was at Stanford at the time. So I talked with, I don’t know, 30 business owners, and three of them told me their password for their payroll provider—let’s call them ABC—was "f*ck ABC." That’s insane. I couldn’t believe I was hearing something like that. 

(14:33) Tomer London 
My conclusion from this—and how it connects to Gusto’s success—is that when you're trying to build something from zero to one, or a startup, focus on where there’s a lot of emotional reaction to what you’re pitching. People are either super pissed off or super excited. The 90% in the middle doesn’t matter. When you show your product and people say, “Yeah, that’s cool,” or “That’s nice”—not good enough. You need them to say, “Holy sh*t, this is incredible!” and want to use it. That’s hard to find, but it’s something you have to aim for.

(15:30) Carlos 
You have another hot take about how data-driven PMs should be, especially when building something from zero.

(15:39) Tomer London 
Yeah, that’s the thing. We’ve grown up with the lean startup movement and product management practices from companies like Facebook, where it’s all about being data-driven. The idea is that decisions aren’t made by gut, but by data, experiments, and letting the data tell you what to do. The problem is, especially if you're building for small businesses, or just starting out, the number of customers and data points isn’t going to be big enough. So you run experiments, but you’ll never reach statistical significance, or if you wait for it, it’ll take forever. So either you cut the experiment short, or you’re too slow. Both are bad outcomes.

(16:33) Tomer London 
In my opinion, and this comes from my background in machine learning and statistics (I was on the way to a PhD), while I love data, in the world of product creation, before you have large numbers of customers—and even afterward—you’ve got to trust your intuition, built from thousands of customer conversations, to make decisions. Use data for smaller decisions and experimentation if you have enough data, but you can summarize it as: instead of being data-driven, be data-aware. I’m not saying wake up and decide randomly, but build your intuition by talking to customers.

(17:59) Carlos 
Sometimes I’m in meetings, and I hear someone say, “We need to A/B test that.” And I’m like, I know A/B testing has its place, but sometimes it becomes a weapon to slow things down. Do we really need to test that? It could take forever.

(18:22) Tomer London 
Yeah, exactly. I love how you say it becomes a weapon to slow you down. It’s not that anyone wants to slow down, but they lack confidence. There’s this two-by-two: confidence on one axis, humility on the other. Many PMs were trained to have low confidence and high humility, like, “Hey, we don’t know. We have all these customers. Let’s use the data to decide.” Very humble, but not confident. I advocate staying humble but also confident. You’ve talked to customers, built intuition, so go build the prototype and ship the V1. Then be humble by listening to feedback and iterating, but don’t fall into analysis paralysis.

(19:53) Carlos 
That’s what I call product sense.

(19:56) Carlos 
I’m curious about your product expansion story. You started with the SMB segment and payroll, but now Gusto is a full-on platform with offerings like hiring, onboarding, and benefits. How did you go about picking what’s next and integrating it into your existing product?

(20:23) Tomer London 
Yeah, yeah, totally. Okay, so first I would say, let's talk about the target customer. I think the most important question to know about any company, when I think about wearing an investor hat and I talk with a company, is, "Is this a good company or not? How is their trajectory going to look?" It's always about who is the target customer, right? And then how do you build a great product for this customer, a great service for this customer, and pricing for this customer? The customer segmentation is really the most important question to determine the path of your company. Choosing a customer is the most important decision. For us, since the early days, we chose small businesses, and still today, it's our focus. Now, to clarify, we have customers with 500, 600, 700 employees as well on Gusto, but most of our customers are under 100 employees. So that's really our focus today. 

So when we started, we noticed that there were a lot of software companies focused on consumers and many on enterprise, but for small businesses, there were very few. Honestly, it was Intuit. That was the one company. And then you had some startups back then like Square, which is no longer a startup but was just getting started. Shopify was just starting. So it was very contrarian to focus on small businesses. Some early potential investors didn’t like that and really pushed us off market. We never did that. We always said we're focused on small businesses. And there are two reasons for that: First, the need was very high. When we talked with small businesses, we saw that they had the pain and the need for us to solve payroll, benefits, HR, and all these different problems, right? Second, unlike before, starting around 2010, people were starting to trust the internet more. If you rewind the clock to the first decade of the 2000s, online business banking was just being introduced, and it took a while to gain trust. But by 2010, small businesses trusted the internet with their banking, which was a huge step. It was a great moment for us to say, “Hey, people are now going to use the internet to run their payroll and business.” If we had started five years earlier, it wouldn’t have worked—the trust wasn’t there. If we had started five years later, it would have been too late. So timing was really important. 

Now, regarding expansion. We’re focusing on small businesses. We’re not going off-market. We have 6% of over 300,000 small businesses today, which means 94% more to go. So we're really focused. When we started, the focus was always on how we can help companies start, build, grow their teams, and make them successful so the business is successful. It's that win-win situation. From a vision standpoint, we knew that’s where we wanted to go. It was just a matter of time to do it. So the question is less about whether we should offer benefits, time tracking, or performance management and HR; it's more about when we’re going to do it. That’s the easier question to answer. The answer is, you don’t expand if your core product offering doesn’t have high product-market fit. So we only expanded when we felt like we had extremely high NPS—most of our history, we were above 80 NPS. Only when we felt confident that there was strong product-market fit did we allocate about a third of the team to work on the new thing. Then, we repeat that process. So, the timing comes down to product-market fit and resourcing.

(24:35) Carlos 
And who do you pick to go build a new thing?

(24:39) Tomer London 
Yeah, that’s a great question. So, the folks who are often zero-to-one type people—you’ve got to identify them. You need to know how to pick them because they’re the right people to start a new product. In the early days, when you're a company of 30, 50, 100 people, almost everyone is a zero-to-one person. But when you're a 2,000-person company, it's different. You need experts in scaling, and there are fewer and fewer zero-to-one people. So, identifying them is key. I would say, first, start with a very small team. Even if you have a grand vision of making a huge business from this new product, you’ve got to start super small. Two people, maybe three. I don’t like having just one person start on their own; two people bring accountability and collaboration. 

The second marker is they need to be full-stack. What does full-stack mean? It depends, but, for example, it could be an engineer who also does product, an engineer who also does design, a PM who also does design, or even a marketer who can do product management and customer support. You need people who aren't constrained by a single box, but who can think expansively. Finally, they need to have a chip on their shoulders—motivated, hard workers who want to get it done. They need to feel like founders. They’ll pull all stops to make it happen. That’s for the team. Now, how does a big company enable a small team to be successful? That’s another question.

(26:27) Carlos 
Well, let’s dig in. How do you ensure they feel supported by leadership but still manage expectations when they achieve success, especially in relation to the overall success of the core product?

(26:29) Tomer London 
Right? Yeah, that's a great question. Because if you put yourself in the shoes of a large company's management team, even if you have a small team that’s reached a million dollars in revenue in a year—which, in the startup world, would be amazing—if you’re making a hundred million or a billion dollars a year, it’s not even a conversation. So you think, “Hey, there’s this talented group of engineers. Why don’t we put them on the big stuff?” It’s so easy to get this wrong, and most companies do. We're all trying to get better at this, including Gusto—we're not perfect. 

Here are some things that help us do this well. First, start with a small team. Second, carve out resources. Carving out means that during the budgeting process in the product or engineering organization, these resources are untouchable. You can’t move resources between zero-to-one efforts and the bigger ones. It's a top-down decision at the beginning of the year: X amount of resources are carved out, and you can’t touch them. Next, set goals and milestones ahead of time. We use something similar to the venture model. Here's the milestone for the seed round, the milestone for Series A, and the milestone for Series B. Each has a timeline, like six months. Let’s say Carlos and Tomer are going to build this new business. In six months, they need to have a working prototype and 30 customers excited to buy it. When they hit that milestone, they get one more engineer. Then, for Series A, they’ve got another six months to a year to launch a product and reach $300,000 in ARR. When they hit that milestone, they get five more engineers. 

This helps align expectations for the small team and the big company. When we review the team’s progress at the end of the round, we can say, "Here’s what the team did, and here were their goals." It gives leadership confidence that they’re meeting their goals, even if they’re small goals compared to the core business.

(29:26) Carlos 
I think Google had a good model for assessing the maturity of a product and deciding when to "graduate" it and give it "adult" treatment. I think they phased it in a way that good experiments didn’t die just because they weren’t overnight successes.

(29:43) Tomer London 
Yeah, exactly. The adulting phase is interesting. When we started the benefits business, it was literally two or three people working in a basement with no windows—I was one of them—and it was super fun. We built the benefits business and hit milestones. When we reached tens of millions in ARR, the team was about 40 people. At that point, we had to graduate them and bring them back into "Big Gusto." That process was much more complicated than I thought. In my mind, I was straddling both worlds: Big Gusto and this new venture, which we called Hawaiian Ice. I thought we’d just wake up one day and all work in the same office, but what happened was the small team had its own culture, tools, ceremonies, and ways of doing things. Bringing those together was harder than expected. 

Looking back, I’d say don’t wait until you’ve reached 40-50 people to bring the teams together. Try to do it earlier, maybe when you’ve got 20 people. By then, you’ll have a nice scale in terms of revenue, and it’ll be easier to merge teams.

(31:36) Carlos 
Well, let’s talk about what’s next for you. I know you recently released Gusto Embedded. I’d love to hear more about the rationale behind not just enabling services for your current customers, but leveraging them as a channel for their customers as well.

(31:52) Tomer London 
Right, yeah. Well, Gusto Embedded is the part of Gusto that I'm most excited about today. I think it represents the future of the whole industry. Gusto Embedded is built around the idea that if you are a small business platform—like a big bank, Chase Bank, or an accounting technology company like FreshBooks that has tens and hundreds of thousands of customers—or if you're a vertical SaaS platform, like Vagaro, which does vertical SaaS for spas, you want to offer an all-in-one solution for your small businesses. Your solution becomes stickier, more valuable, and provides better economics. 

Payroll is one of those things you’d want to offer to your customers, but it's just so hard to build. There are 15,000 new rules and regulations every year, right? Gusto is an expert in that. So, what we’ve done is build Gusto Embedded, which allows these platforms to go in and build their own payroll product. For example, FreshBooks Payroll, Vagaro Payroll, or Chase Payroll. Their customers can click on the tab and run payroll, and everything is connected. It looks exactly like it’s part of their platform, but behind the scenes, it's powered by Gusto. 

This is something we’re very excited about because I believe it’s the right thing for the customer. If you're already relying on one of these platforms to run your business, it makes so much more sense to bring more functionality into it. Everything is connected: time tracking, payroll, reporting, banking—everything. This is a huge part of Gusto’s future, and it’s going really, really well. I believe this is the future of the industry.

(33:44) Carlos 
Yeah, and as I think about this as a framework for all types of products, I’ve seen many evolve from being a feature into a product, then from being a product into a multi-product or platform. What you’re describing is truly becoming an ecosystem where other businesses on top of your platform can benefit and create their own economy.

(34:09) Tomer London 
Yeah, exactly. That progression you described is typical, and every industry has its own way of doing it. For example, look at the cloud business—Google, Amazon, and Microsoft all created cloud businesses. Initially, they built this technology for their own needs, and then they realized other people could use it. So, they made it into its own business line and product. 

For us, it’s similar. We’ve built all of this technology and compliance infrastructure to use for Gusto. Now, we can take all of that and embed it in other companies’ offerings so they can offer it to their customers. I believe this will make a big difference out there.

(35:06) Carlos 
I don’t think this would be a good interview if we didn’t talk about artificial intelligence. In all seriousness, I’d love to hear about specific use cases and how you’re thinking about integrating this new technology into your product.

(35:18) Tomer London 
Yeah, totally. I’d say there are two areas we’re looking at today: one is customer-facing, and the other is internal-facing. We already have a lot of confidence and results in the internal-facing side. On the customer-facing side, we’re still experimenting. 

For example, on the internal-facing side, we have an AI assistant for every person in our customer care and operations teams. It helps them do their job better—ensuring consistency in how we speak with customers, providing the right information at their fingertips when connecting with customers, auto-completing tasks, and automatically scanning documents and routing them to the right place. These tools supercharge our ability to serve customers well. 

I mentioned earlier that, in the small business case, the service experience is as important as the software experience. Both are equally important to us, which is why we invest heavily in internal tooling and technology. We’ve seen metrics like improved customer satisfaction (CSAT) scores, faster response times, and an increased number of customers that a single person can serve at once. These are the metrics we track, and we’ve seen improvements. 

On the customer-facing side, one of my favorite use cases is when people want to upload a CSV file—a spreadsheet—and just dump it into Gusto. We then figure out how to read that data and apply it to payroll, time tracking, accounting, and more. It used to be really hard to do; we’d provide a template and tell the customer to use it, but they’d say, “I don’t like this template. My business needs something different.” Now, we have this really cool feature where customers can dump their CSV files into Gusto, and we figure out how to read them—hours worked, bonuses, overtime—and show it back to the customer for verification. The accuracy of this feature is over 90%. It’s really, really cool. 

We’re also experimenting with large language models (LLMs) for several other interactions in the product, but those are still in the early stages.

(38:07) Carlos 
I can imagine you deal with compliance a lot, not just for your customers but internally as well. As a product person, I’ve often found that compliance or legal teams aren’t the first ones you put in the classic Venn diagram of product, design, and business. So, how do you think about bringing those teams closer and using them as a secret weapon to build better products without slowing you down?

(38:34) Tomer London 
Yeah, exactly. We hire builders in all the departments you mentioned because our business is helping customers stay compliant. If they’re not compliant, we’ve failed. Now, you’re right—legal, compliance, and risk management are about mitigating risk, and the best way to avoid risk is often to not do anything at all. So, for example, how do you avoid the risk of crossing the street? Don’t cross it. 

We don’t want that mindset here. What we look for and help develop is a builder mindset in our legal and compliance teams. Step one is understanding the risks and putting them down on paper. What are the risks we’re taking? What are the risks our customers will take? Step two is offering options for mitigating those risks because we want both our customers and Gusto to stay compliant. 

Step three is bringing together the compliance, product, design, and engineering teams to build a product that solves these issues for our customers. Usually, it involves giving customers options, making risks clear, and setting defaults that make the best choices easy when they’re building their companies.

(40:28) Carlos 
Tomer, I just found an article on your website that you wrote in 2015 about the five product principles. I’m going to read them because I think they’re incredible. Number one: Show users how much we love them. Number two: Be opinionated, build a future you strongly believe in. Number three: Only do things that are worth doing really, really well. Number four: We are sherpas, make sure the team gets to where they want to. 

(40:45) Tomer London 
Yeah.

(41:01) Carlos 
And number five: Listen, great ideas can come from anywhere.

(41:07) Tomer London 
Yeah. Thanks for sharing that. These are some of the principles we’ve stuck with. One thing I didn’t mention earlier when we talked about different chapters of product management is design. Throughout this entire time, I’ve led product design and data science. At Gusto, product management and design overlap significantly. 

The first principle—show users how much we love them—has two parts. One is understanding, empathizing, and caring about our customers. We spend time with them, care about their outcomes, and aren’t just building tools. The second part is showing that we care. We pay attention to details. When customers notice the care we put into the craft and details of their experience, they think, “You didn’t have to do that, but you did.” That attention to detail shows that we understand and care about them. I love this principle, and we still use it today. I can give you an example.

(42:29) Carlos 
What I like about using principles instead of just values is that principles are ways to put values into action. It makes it easier for someone to fully understand what they mean, rather than just seeing words like “transparent,” “hardworking,” or “smart” on a wall.

(42:46) Tomer London 
Yeah, that’s a great point. We have company values that focus on how we treat one another, how we treat our customers, and what we value as a company. Principles, on the other hand, are how we put those values into action.

(43:18) Carlos 
Tomer, it’s been a pleasure spending time with you and learning from your experience, building from scratch to incredible scale. Thank you so much for your insights.

(43:26) Tomer London 
Thank you. Thanks so much, Carlos.