Episode 31

How to find product/market fit before you start building — UserLeap’s Ryan Glasgow

UserLeap founder & CEO Ryan Glasgow stops by to share tactics for validating startup ideas, approaching early customer conversations, operationalizing product principles, and teaching yourself founder-led sales.

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Ryan Glasgow: [00:00:00] I think as founders, everyone really leans into their own intuition far more than their shed. And I think a great outcome for any business or product or new feature that you're working on is that you invalidate in the very beginning or as soon as possible that it's not worth spending resources and time on. And there are just so many ways to really invalidate by asking those tough questions with actual customers who you hope to serve.

Brett Berson: [00:00:35] Welcome to in depth, a new show that surfaces tactical advice, founders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, a partner at first round, and we're a venture capital firm that helps startups like notion, roadblocks, Uber, and square tackle company building.

Through over 400 interviews on the review, we've shared standout company, building advice, the kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast. In-depth you can listen into these deeper conversations every single week. Learn more and subscribe today@firstround.com

today's episode of in-depth. I'm really excited to be joined by Ryan Glasgow. Ryan is the founder and CEO of user leap, a product research platform that helps PMs, user researchers and growth marketers launch micro surveys to uncover customer insights faster before founding user leap in 2018, Ryan was a PM, an early team member at Weebly, which was then acquired by square and verb, which was acquired by snap.

In his previous roles, Ryan noticed a gap between the fast pace of release cycles and the difficulty in getting high quality search quickly. So with user leap, he set out to build the tool he had always wanted. And so it's clear that he's built something pretty special. His team recently announced that they've raised $38 million on the heels of a $16 million series, a fundraise only six months ago with off the charts demand and a client roster of more than 500 companies, including Dropbox square, Opendoor, and loom.

This team is off to the race on a personal level ever since first round invested in user leap seed round. I've been incredibly impressed, not only with the company's trajectory, but also with Ryan as a founder, as we discuss later on in this episode, I describe him as an intense learning. In our conversation today, we start by rewinding the clock back to the six month period before Ryan started the company.

When he was validating his idea and addressing the crowded market from how he approached segmentation and early customer conversations to common product market fit mistakes. There's so much advice in here for aspiring entrepreneurs. We also get into the product itself, including what the first version looked like, how they think about adding new features today and how user leaps three product principles are used day to day.

Since Ryan's a self-described product guy. I thought one of the most interesting parts of our conversation was on how he taught himself. Founder led sales. He shares the specific tactics that made the biggest difference and walks us through how he's refined his approach into a repeatable plan. From the question he always asks in customer meetings to the books that have had the biggest impact on his development.

There's a ton of really tactical nuggets in here for founders and product leaders alike. I really hope you enjoy this episode. And now my conversation with Ryan. Well, thanks again for joining us, Ryan. I'm really excited about this conversation. 

Ryan Glasgow: [00:04:13] Thanks Brett. Thanks for having me on the podcast. 

Brett: [00:04:15] So I thought one place we could start is by talking about the absolute earliest stages of the user leap journey. 

Brett Berson: [00:04:21] I think the six months leading up to starting a company is some of the most interesting time in the least understood or open sourced in technology. And so maybe we could go back and you can talk about the founding story before you built the first version of the product. And then maybe a little bit about how you thought about building the early version of the product.

Obviously what you're working on is a big multi-year vision and multi-year build. And so we'd love to learn more about how you unpack. Where you want her to go over 10 years in a kind of the first 10 weeks of product building, 

Ryan Glasgow: [00:04:53] taking a step back my career, the first four companies that I joined, it was really pre-product. And a lot of them, they didn't have company names. They were writing their first lines of code or had not even written any code yet. And it was often coming in as front end, engineer designer, product manager, really helping these companies get off the ground. And all four of those went on to be acquired.

One of those was verb that when tech crunch disrupt and was acquired by Snapchat, but I wanted a different experience after that. And so I joined Weebly as the first product manager. And help scale that company from around 40 people to around 300, over a three-year period. And I really wanted to experience that hyper-growth phase of what it's like to grow a company and really see that hyper-growth and work with a larger user base.

Having previously only worked in that zero to one space and at Weebly, I really did gravitate towards a lot of the zero to one initiatives and bringing a lot of the new products and features to market. And after three years Weebly, they were going through a pivot to e-commerce and asked me to lead.

Development of the new e-commerce product line. That was going to be the core of the company, which is now square e-commerce today. And I was burnt out. I needed a break. And so I took a year off to travel and part of the goal was to really explore maybe areas that I didn't quite know. And so when I started to really look at the shift from the downloadable files that are on our computers, to the cloud-based documents, saw an interesting trend in the market and started to really explore that space.

And when I first tried Figma, it really clicked on me if. Downloadable design file can now be fully cloud-based that this is a pattern worth, really exploring. And I started to experiment that space and saw that. First of all, I wasn't going to be a great business because saving people time is often not a great business.

And I got a little bit stuck getting that company off the ground and realizing that wasn't working and came across a book called outcome-driven innovation by Anthony Olwick. And it really broke down the process of thinking through the outcomes that customers are looking to solve. And it really dawned on me of how, just how powerful surveys are gives you is really using the survey based approach to bring innovative new products to market without even writing a line of code.

And I thought that was such a powerful concept and ended up being powerful in two ways. One, because I realized how powerful service could be, but to help me really uncover and think more clearly about an even bigger opportunity than cloud-based collaboration, which was really helping other companies better understand their customers through research and surveys as a technique.

Brett Berson: [00:07:41] Did you go from there? You had an aha moment in reading the book and he thought, oh, maybe there's a new opportunity for a new type of product in the category. And then what happened, 

Ryan Glasgow: [00:07:52] what I noticed is that this could be a new technique for other companies to think more clearly about their own customers. And when I looked at the outcomes that a digital product development team is looking for in a qualitative research solution, Really defined those outcomes and talk to other product managers and founders. What are you looking for in a qualitative research solution and outcomes like low efforts to create surveys low, to no efforts for analyzing all the data, a systematic way to reach out to customers without having to go to my database.

And when I looked at the outcomes that the product management and research and designers that I was talking to, what they were looking for in the market found that the two dimensions fans are really reading those outcomes of satisfaction. And these are all really important outcomes to these teams, but they are highly unsatisfied with the existing tools on the market.

So this was a market that's underserved. And if I can deliver on this set of outcomes that are important to this audience of product managers, designers, and researchers, and I can deliver a product that they are highly satisfied with these outcomes based on what I've built. Then that was really the definition of product market fit before I even had to really build the product.

And so at that point, it was a set of very ambitious outcomes and it took some time to really build and develop that product to achieve those outcomes. But what people will see today with what we've developed with user leap is something that's far different than anything else on the market. And the technology that we've built is highly unique and differentiated, but it all started by thinking around the outcomes and needs of this market.

That's underserved that didn't have a solution that uniquely solved the goals that they were looking for. 

Brett Berson: [00:10:01] I'd be interested to understand what gave you the conviction to build a new type of surveying product. And you're kind of getting at this by these customer conversations, but I'm interested in going back because as a founder that was iterating on different ideas, I would have imagined that you land on the survey opportunity. And then you're like, wait, there's literally 10 or 15 monster companies that have been created just in surveys. It's incredibly crowded. I would assume you talked to a bunch of early angels and investors, and they were like another surveying tool. And obviously what you landed on is an insight that was many clicks deeper than we're just going to grade a modern serving tool.

And so I'd be interested. Do you have any thoughts about that or insights around landing on that idea and maybe not being concerned that there's 20 companies that are doing some version or some taste of what you're trying to. 

Ryan Glasgow: [00:11:00] It was certainly a concern. But when I did the market segmentation, this specific audience of product managers and really looked at the needs of a product manager saw just this huge opportunity of this underserved market.

And this market was growing really fast. Product management is one of the fastest growing roles right now. It's becoming increasingly important for a company's success. And I saw all the tools out there and was familiar with those solutions, those traditional survey platforms. And if you look at their own story, many of those companies were started over 20 years ago now.

And what was really innovative about those technologies is bringing that offline survey online. And that was at the time a very key innovation. But when you look at how we have this rise of continuous deployment and development today, And thinking back to my experience as a product manager at companies like Weebly and Pryor, I didn't feel like there were any solutions on the market that were built to solve the needs that I had.

And through that own experience. And I think any entrepreneur will start a company in many ways to solve his or her own challenge or pain. And this is exactly one of those stories where thinking back to my times as a product manager, I didn't have a great tool set or platform to really communicate with those customers in that systematic way.

And in the early days, it was difficult to really get that conviction. And when I did the segmentation specifically, I saw that the most underserved product management market segment was actually with the larger companies. And so when I think back to the first four companies that I helped build that were eventually acquired and were successful.

There was honestly less of a challenge around the qualitative data because you can almost talk to every customer. But when I thought about my experience at Weebly and we ended up with 50 million accounts, by the time I left, I saw this really incredible challenge of gathering and understanding customers at scale.

And so the premise and hypothesis around user leap was that the underserved market is not only in the product management space and not as a product management as a market, but was even narrower in the high growth two at-scale companies. And let's build a solution that specifically meets those needs up market with these high growth and at scale companies.

And usually from day one was really designed for that specific market and nothing that I had uncovered and really searched around for. Was specifically built for that specific market segment. And I think any time you enter a, what many fill is a commoditized or mature space, you really need to think through your differentiation and your product strategy and your market segmentation to really find where that underserved opportunity is and where you can build that highly differentiated product, that uniquely suits that specific customer segment.

Brett Berson: [00:14:16] There's a bunch of interesting jumping off points from what you just shared. Ryan, I guess one interesting place to go would be to go deeper and better understand how you conducted those early conversations with customers. And I think somebody that's in the surveying and question asking business, you probably did it in a pretty methodical and intentional way.

And so maybe you could take us through some of that early customer discovery, how you thought about figuring out your ICP, which customers to spend time with. And then more importantly, how to spend that time and what to ask so that you can get the most insight as it relates to who to build for and what to build for that person.

Ryan Glasgow: [00:14:59] I started at hypothesize and design with mock-ups and really a lightweight sales stack showing this product. And one of the key learnings that I had early on is to never involve people that you personally know in the customer development process. And I think that folks that have an audience, even a larger audience, you know, an extreme example might be Gary V ever reaching out to their own audience to for customer develop it's often misleading. And so I actually started to cold email founders and product managers at Y Combinator companies. And I had no relationship with them and see if they would respond to my emails. And I was able to get several of them to respond and take meetings with me. And in the very beginning, I really wanted to test and validate whether this was worth working on by seeing of people that I didn't know were willing to spend time with me to help co-create and develop this product.

Because if I'm truly solving a pain that they're experiencing, then they will spend time. And what I noticed with B2B is that time is more valuable than money if you're selling to someone because it's the company's money, but it's their individual time. And they're often very busy with a lot of different priorities.

And so when I started to see who is really willing to spend time with me, and there was a product manager at Hotwire for an example, and he spent probably the course of 12 weeks every week for close to an hour co-creating and providing feedback. And this is someone that I didn't know at all. And when I started to see who is responding to these cold emails, who is following up on those emails and booking time, there a product manager at Intuit as well in the QuickBooks team, very early on in the company.

Spending time and providing feedback on those mock-ups and that deck that I had created. And I started to really hone in and see, okay, I'm starting to validate that these high growth and at scale companies with people that I don't know, this product management segment are willing to spend time and provide feedback.

And they're very interested in the solution because it resonated and it solved a problem that they're experiencing in their lives because the existing solutions to them were in fact, broken. 

Brett Berson: [00:17:09] Talk a little bit about what those meetings looked like. You know, you mentioned there were someone at Hotwire that maybe you spoke to a weekly over 12 weeks. 

How did you structure it and what was going on in those? 

Ryan Glasgow: [00:17:21] I had a deck and it had the screenshots and the different outcomes and features that I was looking to build. And every week we would have this meeting and it was really just showing the progress around the product direction. And the progress that I was making as a product, realistically, we did some demos with his team, but we were very early in our journey and we didn't have a security posture.

We didn't have product that could scale and ended up not being someone who turned into a customer. He's now at a different company, but. It ended up being someone who was providing that feedback along the way and saying, Hey, this isn't really resonating for me. This feature that you designed, or this feature that you're telling me about.

Because if you think back to the beginning, when I thought through the outcome driven innovation, it tells you the outcomes that are important to the audience and the segmentation of where the market is underserved. But then as a product manager or founder, you have to think through how to actually achieve the outcomes that are important to the audience with a high degree of satisfaction.

And so you can't rely on your customers on what to build. They can really only tell you what outcomes they're looking to achieve. And so it was really around the iteration, working with Israeli customers, testing and sharing pain, and really showing them these mock-ups in this different set of functionality and features as on a weekly basis, I was iterating on how to actually solve those outcomes.

Brett Berson: [00:18:50] Do you mind doing a recap or giving us the cliff notes version of this concept of outcome driven innovation and maybe how it's similar to lean startup ideas or other more well-known concepts? 

Ryan Glasgow: [00:19:03] One of the frameworks that is really popular right now is product market fit. And if you look at the most recent iteration of product market fit with the four question survey, and if you use that to find product market fit, they will actually be often a very painful journey for you as a founder.

And I've seen founders spend years measuring product market fit and building an iterating and measuring product market fit, trying to really understand how to get there and they get stuck. And if you take a step back to see the origins of product market fit, it was Sean Ellis who pioneered the framework for product market fit.

And he was a marketer who was looking to join startup. That already had products that customers loved. And so he, we use that question of how disappointed would you be to validate whether companies had product market fit? What I recommend a founder today is using a different framework for discovering product market fit.

Because as a founder, if you're only validating product market fit, it could take you five, 10 years, 20 years of testing a hypothesis. But what if you can actually understand it and what your customers are looking for and measure product fit without actually having to build a product. And so that was really critical for me.

When I came across the outcome driven innovation framework and the quick summary there is first really looking at. The broader market that you're looking to serve. In this case, it could be people building products, researchers, designers, maybe marketers, product managers, and then asking them what are all the outcomes that are important for a solution that delivers qualitative insights and they'll provide maybe 20, 30, 50 outcomes of what they're looking for.

And these are stops. What, what are all the dimensions of a solution and maybe it's insights delivered in 24 hours. It could be something like not knowing how to create a survey and having those really provided for you. It could be not knowing how to analyze survey data and really having a solution that also does that for you.

And once you get those outcomes and then it's serving a broader set of customers, usually 200 to let's say 400. Having them measure those outcomes by the, those two dimensions of satisfaction and importance with the solutions they use today. And so if you surveyed a product manager on Typeform today, and it's a high growth company or at scale company, and you say, Hey, what's important to you.

And what are those outcomes that are important to you with a qualitative solution? Here are the 20 outcomes rate. Each of those by satisfaction and importance, what you'll likely see with a solution like Typeform is that the important outcomes they'll rate those as unsatisfied because it's not meeting her needs as a product manager because she has a unique set of needs.

And so by using that framework, I think it's a great way for founders, particularly early to actually uncover and find product market fit before they even need to develop that product. 

Brett Berson: [00:22:39] And can you maybe talk a little bit about how you figured out in this process who you were building for in the sense that, was it a designer?

Was it a user researcher or was it a product manager? 

Ryan Glasgow: [00:22:52] When I looked at my experience at Weebly and I talked to other founders and product managers, what I saw was that it was really the product manager who was mostly responsible for the success and failure of the product. And most of the research was being really provided to the product manager to empower her decision-making.

And when you think around delivering insights directly to the decision makers for countries that don't have a user research team, it really dawned on me. And when I was talking to these at scale companies that had user research teams, that they were looking for, that solution that made that qualitative data much more accessible.

Because at these larger companies and ad experiences that we believe is that the user research data was very valuable data, but it was often delivered in slide decks. And anyone in particularly today strongly would prefer data to be delivered in a platform or a product where they can really explore.

And first round was the seed investor in Looker. I think that's a great example of allowing the decision-makers to explore the data that they can then form their own conclusions around and conduct their own analysis. And so when you think around the segmentation of who to build for, and who's ultimately making those decisions, I found that the product manager was that decision maker who often didn't have that qualitative data and where they were looking for.

Again, let me look at the outcomes is solution that met those outcomes so that they can make more informed product decisions. You talked a little bit about how you, I ran this process of talking to early customers and looping back over and over again, as you were iterating on what the early version of the product would be.

Brett Berson: [00:24:50] Can you pick up that thread and talk about what you learned ended on terms of the first, fully featured version of the product and how you utilize customer feedback to inform that? Cause I assume you're having a lot of different customer conversations. There's some overlap in some needs. There's other areas that are divergent and you have to pull all of this together into something that you're eventually going to put into someone's hands.

Ryan Glasgow: [00:25:14] Given that the underserved market was really the high growth or at-scale companies. I found it to be incredibly important to only work with companies in that market. Because the hypothesis that I really tested was that these companies with larger user bases, thinking back to my experience at Weebly and talking to other product managers and founders, that was really the underserved market in the qualitative space.

And so when I had those early conversations, I actually kept it to a very small set of customers. And through the wheelie connection was able to start working with square and it worked with the square team and some of the early customers that we had, like plan and thinkable and square, they all had a user base of at least 500,000 users using their product on a monthly basis.

And given that it is difficult and it takes time to build a robust platform for a high growth or at-scale company. What I had to do was only develop the piece that I couldn't manually do myself. And so the only, the first vision of user leap was only the STK. It was a piece of code that these companies could add into their product.

And there is a place to log in to view the raw data. There are responses, but everything else was completely manual by myself and the people at the company. And so to launch a survey, you wanted to change a survey question. You want it to stop a survey. You wanted to choose where that survey, where it appeared in your product, or you wanted all that analysis of that data.

I was doing all that myself and the team at usually if we were all doing that ourselves and customers would say, we want to launch a new survey, we would go into the product and change the code. And through the STK that was installed in their product, we would update all the configuration and then it would update.

The STK and what was actually being displayed in their product, but on a weekly and monthly basis, I was building out Dax and analyzing the data for them. They were getting me as their product manager and researcher building Dax saying, Hey, I look through 2000 survey responses and I've analyzed everything for you.

Here's a deck with all the analysis for you. And when I started to really see through all of this manual interventions, what was really working and what was clicking and where the positive feedback was, we started to focus our development efforts on those areas. And so we started to hire a PhD data science team started to bring in engineers who had built infrastructure at scale, started to build out custom surveys and changing survey questions and dynamic targeting.

And the Israel features that took at least a year to build because they're incredibly complex to build at scale. But by doing that manually at the beginning, It allowed us to really validate the product that we are building was solving those outcomes that we had originally set out to solve. That makes a ton of sense.

Brett Berson: [00:28:26] That's very cool. Did you ever get concerned that you would fall into the trap? The classic? Oh, that's great. But you're basically a consulting company really haven't proved anything.

Ryan Glasgow: [00:28:36] It was certainly a thought in the beginning and some people in the beginning thought, are you a service? Are you a product?

But as a product manager, I knew that we could build everything that we are really doing manually. It would just take resources. And that really served as some of the conversations with investors saying that we're delivering these really key insights for these customers in unique ways. We're starting to really see this product work, but we've only built 5% or 10% of even an MVP for a company of this size.

And it's going to take more resources to really continue to build out this product and to continue on this mission and really serving these product managers and researchers for these at scale and high growth companies. And so I'm the type that will always do things that don't scale, particularly in those zero to one phases.

And this was absolutely one of those examples and something that really helped us get to an incredibly strong product foundation that we have today. A lot of these early conversations going back and effectively creating results or reports in Google slides versus in the product. 

Brett Berson: [00:29:48] Were there specific questions that you would ask in those meetings that you found particularly illuminating?

Ryan Glasgow: [00:29:54] I don't think there are any particular questions or breakthroughs, but it was really just spending time with them and seeing next week. Help us understand what's working or not working here. I still do this today. I met with one of our largest customers yesterday and asked what are the highs and lows with our product right now.

And I treat customer development as really a one-on-one with a direct report. And any time you're having a one-on-one or your meet with a customer, you just want to ask the hard questions, ask the customer yesterday, one of our largest customers, right on the call. This is the head of product zero to 10.

How satisfied are you with usually as a company and help me understand what we could do to get you to a 10 and asking product market fit questions to validate right now we're running product market fit and user leap to validate whether we have product market fit. And the good news is we do have product market fit.

And so I don't think there's any really innovative questions to ask, but it's really just digging in and asking the tough questions to make sure that customer. Really cares and that you're really learning both the positive and the negative more importantly, the negative about what's working with what you've built so far.

Brett Berson: [00:31:11] One of my theories around why founders don't spend more time with customers or seek critical feedback is that it's an incredibly unpleasant experience that, you know, people criticizing your baby is very unpleasant. And at the same time, that's where a lot of the best insights come from. Is there anything that you do to manage that discomfort or does it just not bother you?

Ryan Glasgow: [00:31:39] I'll was hesitant in the beginning of my career and when I first came across. The product market fit framework from Sean Ellis. About 12, 13 years ago, I was at the first startup that I had worked at as that really early stage designer product manager. And I went to the founders and said, I want to ask this question, this product market fit question.

And they said, no know they were honestly, they didn't want to know whether we had product market fit. And I thought to myself, I'm spending all this time at this company and we don't want to ask the tough questions. And if your team isn't able to ask the tough questions, then why are you there? Why are you spending all of your time on this product?

If you don't even know if it's worth your time. And so I think that you have to lean in to ask those tough questions. Otherwise, why are you there? Who are you building for? If you're not willing to ask those tough questions. So you think you're probably wasting your time and there's a good chance you are wasting your time.

Because you're probably going in the wrong direction. If that's uncomfortable for you to ask 

Brett Berson: [00:32:44] on a related note, you've sort of touched on this in different ways, but when you reflect on your own journey and you look across all the super early founders that you spent time with, are there consistent mistakes that you think that founders tend to make maybe specifically around this voyage to product market fit, or maybe it's just building early products?

Ryan Glasgow: [00:33:06] I think as founders, everyone really leans into their own intuition far more than they should. And I think the, a great outcome for any business or product or new feature that you're working on is that you invalidate in the very beginning or as soon as possible that it's not worth spending resources and time on.

And so I have worked with founders where there is strong intuition around building a product where a feature and bringing that to market and. There was no real user research process and no difficult, uncomfortable questions were asked very early on. And, you know, again, I think that it's just an incredible mistake in disservice to everyone involved is I recall it when company where the founder had very strong intuition and inclination around bringing a new feature to market.

And it took this team about four people a year and a half full time working on this feature. And there was no user research that was done. And when we launched it, we actually didn't even launch it. We launched the landing page for the feature and we linked from the homepage to this feature. And no one clicked over to that landing page and no one opted in to even try that future.

And we are weeks away from launching after a year and a half and we just shut it down. And there are just so many ways to really invalidate by asking those tough questions. With actual customers who you hope to serve with those features. And I just think that it's something that we, as an industry and as founders and product managers use to ask those questions to really challenge those that are responsible for asking those uncomfortable questions, to ask those on your behalf.

So you can get those answers to really understand is this worth spending time on and really validating or invalidating that theory or hypothesis that someone has to bring that product or feature to market. 

Brett Berson: [00:35:11] Can you talk a little bit about the way in which you build products in each one of these phases?

Now that you're a much more mature company, you talked a lot about what that loop looks like when you're like a three person team talking to customers, doing things that don't scale, creating these insights and dashboards in Google slides. And then the first version of the product that instantiated those insights in the actual product.

And maybe you could pick that thread up and talk about what that loop looks like. 

Ryan Glasgow: [00:35:39] Now, I would say that in many ways, there are a lot of patterns to the early iteration and feedback loop and user research process. And for an example is that it's very customer driven and we had a product manager join a few months ago and I made a promise to her that usually it will be the most customer driven company you'll work at.

And we have shared slack channels with, for many of our enterprise customers. And I'm constantly joining customer calls, joining customer success calls, doing skip levels as CEO, meaning directly. Those had a products, head of user research and really hearing what's working and not working for them, but the bringing new features to market, it still comes back to talking to customers and understanding what they are looking to achieve.

And in many ways, once you have a core product that is solving a problem, the best way is to look at the other vendors and products that someone is also using and think about ways that you can uniquely solve those. And so maybe you're not exactly doing what that other vendors doing, but you think around the outcome that your customer is looking to solve and achieve with those other vendors.

And think how as a company, can we build something that actually solves that same job or that outcome in a way that's unique and. True to us as a company. And I think if you look at fig jam, I think that's a great example from Figma, how they're taking this concept of virtual white boarding and they built a feature around it.

And I'm sure they saw a lot of their customers were using Figma for high-fidelity design and prototyping, but that ideation phase in design, they using other vendors. There's a lot of virtual whiteboard solutions out there. And they saw that there's such a high attach rate to Figma with other virtual whiteboard solutions like Miro or a mural that let's think about how we can uniquely solve this outcome of this ideation and discovery process in the design phase so that our designers don't have to switch tools.

And when you look at the customer jobs flow, there's typically about eight different steps in the customer jobs flow of someone starting an action and completing an action. And you can really apply that to anything. Product that you're working on and look at the steps that you're solving today. And then look at the ancillary steps that you're currently not solving and think around how you can build out and solve other steps or other jobs that are ancillary to your core product.

And so that's really where we're focused on right now with our latest funding round is thinking on how we can solve ancillary jobs, that our customers are also looking to utilize the usually platform for 

Brett Berson: [00:38:41] this gets into one of my favorite topics, which is mano product companies versus multi-product companies.

And if you look at the really durable, special companies, they're all massive multi-product companies. And you're at this kind of inflection point where we have this core product, that just the core thing that you're doing, you could spend 10 years working on and consume all of your resources. And at the same time, you know that at some point you have to be a true multi-product company, if you want be one of these iconic companies.

And so can you tell, talk a little bit more about how you figure that out? Do you start with the most near adjacent opportunities that you hear from customers? Do you zoom all the way out and think more holistically about everything in and around and what you're currently doing? Or do you think about things that maybe are slightly unrelated, which seem like the hardest thing?

Ryan Glasgow: [00:39:35] It's certainly a very difficult problem. And I think that companies that achieve and find product market fit for their first product, you have to find to hit that next phase of growth. What is really that next innovation or what's that next job that you can solve for your customers? And I have seen many companies get this wrong, where they build something that is perhaps tangential to what they're doing today.

But they don't end up seeing the inflection point of growth that they're ultimately hoping for. And the two fundamental rules that I think is really required to expand from a single product to a multi-product is first looking at the category that you're in today. And we are in the research category and there's a lot of different jobs that our customers are using usually and other vendors, for addition to use leap, to really solve various qualitative insight jobs that they might have to build better product experiences.

I think a lot of companies might build, let's say in one category, but they look to expand into other categories. And a great example of looking at how categories really mapped today is even go to G2 crowd and look at how. A company like G2 crowd is categorizing and defining different categories. And if you're a company like Figma that is perhaps serving designers and you look to build a solution or a product that is in a different category, let's say Figma built a research product.

You know, let's say user leap built an analytics product, or if we built something in a completely different buyer, then that's typically where I see the failure is that you're not really building within your category because consumers today, they look to really spy vendors that solve one type of need.

And I think one example of perhaps a company that isn't doing a great job of this is Intercom and Intercom started out with this really great chat product. And everyone loved Intercom for the first three to five years. But they started to move into other categories. Like recently they've really focused on engagement around guides and tool tips and walkthroughs.

That's complete different category and they're really solving a product manager's needs by building guides and tool tips. And walk-throughs where their core product was in the customer success category. And I believe that if they had focused on the customer success category and built out other jobs and moved up market, that we be hearing much more about Intercom than we are today, because they've tried to span multiple categories and build a platform that is serving multiple buyers and it ends up diluting the offering because to move up market, you really need to serve one buyer, but continue to build a platform that can serve the more sophisticated needs of that buyer.

As the company grows. And so one is looking at the category you're in today, looking for the ancillary jobs within your category and look at how you can uniquely solve those jobs. And also looking at the products that they're also buying today as the biggest opportunity. And the second one is really looking at the market segments.

So at user leap, we are positioned right now on the high-growth and at scale tech companies. And we're really focused now on building for all market segments, small, medium, and large. So we're actually moving market in many ways. Most of our first customers and earliest customers were all high growth or at-scale companies.

And so as we move down-market, I'm now looking at what are the different features and jobs and use cases and outcomes that our customers are looking for that span all market segments. And so if you're a company that. Is perhaps starting in SMB and you're looking to move up market. Then it's looking at what are the features that our customers use today, but let's reach out to those larger customers, the buyers that we want to be serving in our current category and understand their needs and build their needs and then move up market.

And that's when you see companies like Datadog really have this explosive growth because they first serve SMB and they continue to build a sophisticated product that serve the needs of larger organizations. And they're able to grow as their customers grew. And now, you know, enterprise is one of their largest customer segments.

Brett Berson: [00:44:42] This touches on, I think, some of your ideas about the importance of establishing product principles throughout the company's life. And maybe we could use as an opportunity to talk about what your product principles are and maybe why you've chosen. 

Ryan Glasgow: [00:44:56] The three product principles that we have today at UserLeap. One is make it not feel like work and seeing the shift of the consumerization of enterprise. If you look at companies that we use today, many of us are using tools like notion, Figma air table, and I think they've done it. Incredible job of reaching those end users. And those end users are bringing these tools into the workplace.

And so really wanted to lean into that so that these end users are trying to use early, perhaps even with our personal Gmail accounts or personal use cases or personal projects, or maybe in very small use cases and really get excited about usually been, want to bring this in and introduce this company into their product.

And if you look at the broader research space, a lot of these companies feel more corporate and they feel more enterprise and Brett, as he pointed out, this is a space that is competitive and it does feel mature. And so how can we do something that's fresh and really modern? The second principle. Is designed for the first time.

And thinking back to my experience at Weebly, 60% of our customers were building their very first website. And so the usability at Weebly was so critical and everything that we did every line of copy, every pixel, every interaction we had to really make the website builder process incredibly easy so that someone who did, I didn't even know what a domain name or hosting or SSL, they did not know what any of these concepts, how can you really help them build their website and bring that to market.

And with user leap, many of our customers have never run a survey before. And so how can we make this research process approachable and accessible and easy. And with our land expand model, we see a product manager bringing usually into her workplace and she might invite an engineer and that engineer comes in and he lands on a setting screen or a connect screen.

He might not know what usually it is. He might not know anything about us as a company or a product, but how can we quickly orient and make that screen as easy as possible? And so our goal is when you look at every screen that we work on, how can you really make it? So that, that screen by itself, it is completely approachable and standalone that anyone can start on that screen and then navigate to other areas of the product.

And the third is consistency is key. When you look at the user to really build a product that reduces the cognitive overload, as much as possible, you have to reduce the mental models of the UX interactions and design patterns to as few as possible. And so consistency is key is not only applied to the design patterns within user leap, but I often encourage our design and product team to reach outside of usually.

And it, for example, when we're building out advanced permissions or team management, let's not reinvent new design patterns, let's find the companies that do it the best, and let's actually borrow and be inspired by what they've come up with, because we know that if someone's using notion and they're managing their team and notion, and we feel like that's a great experience and they come to user leap and they also need to manage their team, we've actually had a consistent experience between those products and they already understand that mental model of how to use that feature.

And so it really breaks down the barriers for learning new parts of your product. If you focus your innovation to only the core, most innovative areas that you're working on and thinking on how you can apply as much consistency across your own product, the modals and the interactions and the flows across your entire product, as much as possible.

But also to the consistency, to other products in non-core areas, they're not critical to the success of your business. 

Brett Berson: [00:48:53] That was a great overview. And so if I was a fly on your virtual office wall, what would it look like to operationalize these or make them applicable, or make sure that they're actually guiding everyone's work versus being something you talk about at the beginning of the year and never think about 

Ryan Glasgow: [00:49:11] it's something that is enforced in every decision and when I'm constantly reviewing design work, when we're iterating on designs and we're thinking through product specs, it's, let's really unpack what we've done elsewhere.

Let's look at the prior art that's already shipped and developed and provided to our customers. And let's see if we can really borrow from those principles or maybe we find a better way for that specific interaction. Let's apply it across. The entire platform so that we can maintain that consistency across all of the UX patterns that we've established.

One specific example is that on our surveys page, we thought about, should we do a list view with the table, or should we do a tile view? And there is this discussion internally around the tile view, which allows to bring in colors and icons, and it would have this more playful feel to it. And if you look at the products that we use today, like a sauna and air table, and you look at the components, their default is actually the tile view and they'll have those colorful squares with those icons.

And when you look at that screen, it feels like something that's really drawing you in our engineering team actually felt very strongly about the list. And just having this kind of Excel style view, where you can sort and quickly scan and find what you're looking for. But when you want to make it not feel like work, do you want to make it feel like a spreadsheet?

And is that spreadsheet really something that's going to invite you in to the survey data? And so we went with that tile view. And if you look at our survey page today, it has all these colors and icons and we still have sorting and filtering. So people can quickly find what they're looking for, but it really embodies that consumerization.

And, you know, maybe it does take slightly a little bit longer, but we like, it was a consistent design pattern that we were seeing on other yeah. Products. And it really embodied that value of not making it feel like work. 

Brett Berson: [00:51:22] That is an awesome example to bring it to life. Thank you for sharing that. I wanted to switch gears a little bit and. Go from product to sales. And one of the things that I've been absolutely blown away in our time, working together over the past couple of years is that you're just this intense learning machine. And if you take something like founder led sales and figuring out sales for the first time, a lot of product and technical oriented founders, it's always sort of an Achilles heel and you, I think have done the opposite.

You've said, I need to be exceptionally good at this. And you've learned at this incredible pace around how do you bring a product to market for the first time? And so I was interested in maybe learning about how you approach learning this and how that translated into how you started to stamp it out from a go-to-market perspective and go from one customer to five customers to 10 customers.

Ryan Glasgow: [00:52:14] I had prior to usually never worked at a company that had a sales person. And so when I identified this underserved market of high growth and outscale companies, I knew that it would take. Sales approach. And we didn't publicly launched user leave until December, just six months ago, I was meeting with every customer who paid us any money until about six months ago when we started our sales team and it ended up allowing us to build this incredible foundation of a product and a company where we're really seeing the pain and the learning for me of figuring out how to sell the product and iterating on the product and meet with customers and making those changes to the product very early on.

And to your point, Brett , I jumped right into books. Anytime I don't how to do something and I get stuck, I immediately start reading books and I read probably six or seven books on B2B sales. And I read a lot of articles online about how other founders made the shift. The one though that really helped me understand how to sell.

It's, uh, it's an older book in a, fill it a bit outdated. If you read it, it's called you. Can't teach a kid how to ride a bike at a seminar. And that book really had a lot of the breakthrough concepts for me. And through that book and through some mentorship and advisors was able to really develop the sales process and sales skills up until our series a as a company and bring in some fantastic customers who are using our product today and enterprise logos through me learning how to sell and working with them to solve their problem.

Brett Berson: [00:53:56] So let's spend a little time talking about this. Maybe start by sharing some of the key principles that you took from you. Can't teach a kid how to ride a bike. Maybe we'll start there. And then we'd love to go into what your founder led sales process actually looked like in the early days. 

Ryan Glasgow: [00:54:12] One of the principles that I found was really fascinating was ensuring that there is no pressure on the individual that you're working with. And what that means is that every conversation that you have, you never want to create the situation where they feel like they have to make this big decision on the spot. And one of the tricks that I learned is that at the beginning of every meeting that you have with a potential buyer or someone who might use your product, the beginning of the meeting always let them know the decision they need to make at the end of the meeting.

And it's called  where you're breaking up this long, really big decision of whether to make potentially this annual or multi year commitment to your product. We are breaking up into these many decisions. And so perhaps that first call that you have with someone responds to your email and says, Hey, I'd love to learn more, starting the call and saying, Hey, nice to meet you.

Maybe share a little bit about who you are and say, by the end of this meeting, I like to know. And I'm going to ask you if you like. To set up a follow-up demo with me, and then everyone understands the goal of that time together. They're not buying something. They quickly helps them understand and orient around how to spend the next 30 minutes because they just need to get to that.

Yes or no decision. And it's a no is totally fine and actually encouraged if they don't want to move to that next meeting. But it ends up creating this process where there's actually no pressure along the way. And this individual knows that many decisions that she's making and at the very end, they will then potentially move into committing and making that larger decision of committing to a contract.

Brett Berson: [00:55:58] Can you share more about if you went back to the pre series, a founder led selling that you were doing, what a week look like, or what were the key activities you were doing to grow the customer base yourself as the founder?

Ryan Glasgow: [00:56:12] It was often relying on at the time the investor interest. So Brett from you and from bill and from mark and the first round team and our other investors who are really facilitating that process of bringing in people that, again, I didn't know, but it was a warm interaction and spending time with that individual understanding the challenge that she was having, and then showing a little bit about the usually product and seeing if there's any interest there.

And so a lot of it was filling up the calendar with these meetings of these product managers and user researchers at these high growth. And outscale companies to see if user leap could solve a product or business challenge that they are facing today. Maybe they didn't have a product business question that we could solve right now and let them know.

Keep us in mind for the future. And many times they came back and ended up becoming a customer, but it was quickly validating and qualifying and disqualifying, these conversations. And these leads that we're getting your investor network. And then when we saw the product manager, our researcher, where we could solve that challenge today, they were facing that onboarding drop off, or they were seeing that increasing churn with their subscription.

They're looking for ways to drive adoption for their product. Then we'd often move into a trial phase and I didn't even talk about pricing or try to sell them anything. It was really around getting them set up with the product and then having them install our STK into their product. Often before a contract was even signed, we need 

Brett Berson: [00:57:52] to put a bow on your ideas around this topic. If a founder reaches out to you today and says, Hey, I'm embarking on founder led selling for the first time we have an early version of the product. We have our first three customers. They seem to really be. Finding a ton of value. What should I be doing? Or can you teach me what I should be doing? What's sort of the playbook that you would be sharing with him or her.

Ryan Glasgow: [00:58:12] If we're starting to see traction and you have a cup of customers today, and you're really looking to accelerate and bring on more customers, the first is really generating the opportunities and the leads. And so where are you going to get those leads? You might want to hire an STR to help develop those leads.

Perhaps you want to rely on your investor network, provide those leads or opportunities. Perhaps you have your own network, although that's often, again, not recommended given that established relationship can lead you in the wrong direction, but look for ways where you can get that repeatable set of opportunities on a weekly basis so that you can have those conversations with those customers where you believe you have product market fit.

And once you start to find that repeatable way to develop those conversations, those initial discovery calls, it's really starting to develop that playbook. And every meeting I recommend starting a Google doc and writing down an outline for what you think that sales process is. And every meeting that you have write down, what's working and iterate and really remove the pieces that are not working.

And over the course of a year, nearly all of last year, I started with one way to sell the product. But over this 12 months, Was constantly adapting to what we have today, where right now the playbook is so repeatable that anyone really at user leap can look at what I'm doing and what I did last year and continue to replicate that now that we have a sales team and we're growing our sales team, and you want to see the consistency of who you sell to who is that ICP?

Is it a product manager at small companies, a product manager at large companies, is that what the user researchers at large companies, there are appealable ICP that you can go to consistently. And that repeatable process in your Google doc really saying first meeting, here's what we're going to cover in the second meeting.

Here's what we got the cover by the fifth meeting. Here's where we want to be in the process. And once you have that repeatable ICP and that repeatable playbook, then you know that you're ready to scale your business to the next phase. 

Brett Berson: [01:00:28] Just to bring that last point to life around the Google doc playbook and the way that it started at point a. And now it's at point B, for example, I think you just mentioned this a little bit, but if I open the doc, what specifically is it there? 

Ryan Glasgow: [01:00:41] What we have is all of the meetings that are required to get to the contract signature and within each meeting, what are the questions to ask and what are the main topics to cover and what is the decision that needs to be made with the prospect at the end of every meeting to continue to the next meeting.

So we think around the submarine approach, each meeting is as contained decision. So what are all the questions and the information that you need to provide to that prospect to help her reach that decision? Only at the end of that meeting to decide whether she wants to continue. To that next meeting. 

Brett Berson: [01:01:28] So I thought to wrap up in our time together, we can talk a little bit about other books or resources or things you've listened to or read that had an out-sized way on the way that you approach building user leap thus far, you already, there's two great resources that we explored a little bit in our conversation, but to wrap up, are there any other things that have had a really huge impact on the way that you think about any facet of, in addition to the two that I mentioned around sales and then bringing innovative products to market?

Ryan Glasgow: [01:01:56] The two that I recommend for a founder or product manager who is maybe earlier, but starting to see some traction, one is user story mapping. And this is one of my favorite books for anyone building products. And it really talks about a story of a founder who built this complex product. And it wasn't really landing and meeting customer's needs.

I think it's a great example.Kevin Systrom at bourbon, where he built this very complex social product called bourbon. And there's all these features, but there's only one feature that he saw customers really using one use case, and it was taking a photo and applying a filter. And when he deleted and removed all of the features that he had built and renamed the company to Instagram with just one feature, taking a photo and applying a filter, we saw one of the fastest growing products in technology history and user story mapping really unpacks the use cases and user stories that customers have and helps really break down and define the areas of where to focus your resources and where perhaps you don't, you're not really going to uniquely solve.

A customer's problem. And another one for companies that are perhaps further along, and this is perhaps the high growth phase is good strategy, bad strategy. And I think that product strategy and company strategy is one of the most underrated skill sets right now, because every year it gets easier and easier to bring a new product to market.

And you look at all the funding that's happening right now, all the new products that are launching every day on tech crunch, emergence of low code development of products. It's so easy to bring a product to market. And once you see that traction, you start to take off. You're quickly going to find yourself.

If you didn't start that way in a competitive. And so product strategy and company strategy is really a key skill set for a founder to know today, to be able to continue to grow and scale a business and win in any market. And so that's another book that I really recommend. It draws in more common examples like Southwest airlines or Ikea, and how they've built this defensible strategy that has not been replicated to this day.

And these were companies started 20, even 30 years ago and longer, but they're still highly differentiated and no one's been able to replicate what they do for a reason. And that's because they have fantastic thoughtful strategy. 

Brett Berson: [01:04:39] Well, that is a great place to end Ryan. It was an awesome conversation and I've had just a lot of fun and really been inspired, having the opportunity to work with you over the last couple of years.

Ryan Glasgow: [01:04:48] Awesome. Thanks Brett. Appreciate since, uh, first meeting you and the team and pitching you all and coming on board in the early days, it's been a lot of fun since then, and just really, really enjoyed past a little over a year and a half now, and we're just getting started. So really excited to see where this goes and you'll continue to hear from me.

I'm not going anywhere. 

Brett Berson: [01:05:09] Awesome. Thank you so much for joining us.