How UserLeap Landed Over a Dozen Enterprise Customers on a $700K Pre-Seed (Interview with Ryan Glasgow)

Host Introduction and Ryan Glasgow's Background

Nathan Latka

00:01Hello, everyone. Nathan here. My guest today is Ryan Glasgow. He was previously on the early team at Weebly, obviously acquired by Square, also at Vurb, which is acquired by Snap. He was also at Extrabux, which is acquired by Ebates, Livefyre by Adobe, and Graph Science by Centro. You can probably guess he's based in San Francisco. That's how you get that kind of history, Ryan. Now you're working on UserLeap. You're ready to take us to the top?

The Problem Behind UserLeap

Ryan Glasgow

00:23Yeah. UserLeap, a sixth startup here now and helped quite a few other companies get started, and really grow, and launch, and build out their customer base. And, you know, one thing that I always found particularly at Weebly is that companies at scale, it's always this continuous journey of understanding those gaps between what your customer wants with your product, and that marketing product experience that you're delivering. And it's not something that just early stage companies need to

00:48figure out. It's a continuous journey, you know, even beyond IPO, and to continue to grow from there. And just found out that it was incredibly difficult, particularly for companies at scale, more or less, even early stage as well, but companies at scale, very, very difficult. So it is a problem that really resonated with me in my past.

Business Model: Pure-Play SaaS and Revenue Model

Nathan Latka

01:06Hold on, hold we jumped ahead of the problem here. So tell people what UserLeap does, and and are you pure play SaaS? Like, what do you think the revenue model is gonna be?

Ryan Glasgow

01:15Yeah. We are a SaaS business. What we do is we help companies understand using microsurveys, their product and marketing experience, and how it actually is able to fulfill the customer need and and what that customer is looking for with that product or service.

Nathan Latka

01:29Yep. And now you told me beforehand, so you're just now launching. So you're pre revenue. Right?

Ryan Glasgow

01:34We do have paying customers. We are live. We're launched with, we are live with customers.

Nathan Latka

01:40Okay.

Ryan Glasgow

01:40You know, right now, we're still staying low and and really focused on delivering amazing customer experiences. And so we're, you know, gonna be sharing more details publicly in the future.

Nathan Latka

01:50Yeah. No. That's great. So so... Okay. I guess put this on a timeline for me, then I wanna get more into patterns you've seen at the experiences you've had. So you launched the company in what year?

Company Timeline and When Customers Came On

Ryan Glasgow

01:59Started UserLeap last year, early last year in in around February. And since then, we've building it out. We, you know, really started working with customers last summer.

Nathan Latka

02:10Okay.

Ryan Glasgow

02:10And they went live with the product. They started to see a lot of value out of it, and started to build out that initial early set of customers as we continue to build out the product offering.

Pricing Strategy and Enterprise Focus

Nathan Latka

02:19Okay, that's great. And then what have you I mean, how did you know, it's a beautiful moment to go kind of figure out your initial price point you're gonna market with. And this is very much like an art, I'd say not a science. You've done a lot of pricing being at, know, six different companies. So what price point did you decide to go to market with for UserLeap?

Ryan Glasgow

02:36You know, early on, it was really about asking people to pay something that was meaningful to them. For every business, it was different. You know, there are different sizes, different revenue points, and it was really a one on one conversation with all the companies. And a lot of it was through my personal network saying, hey, how big of a problem is this for you? How much would you pay? And it started with there.

Nathan Latka

02:56This is, I mean, it sounds good though in theory, but this is very difficult to actually quantify, right? You're going, Hey Nathan, I'm going, Yeah, I want to use UserLeap, Ryan. I love you. I worked with you at Weebly, man. I want to support you. And you're going, Great. How are, know, how big a problem are customer surveys at your company? I'm going, Right, I don't know how the hell to quantify that, but I want to

03:11pay you to support you. Right? It's like, I mean, how are you actually quantifying that?

Ryan Glasgow

03:16Yeah, in terms of quantifying, our goal is to actually help drive funnel conversion from homepage to churn. And so what we can do with our pilots is actually...

Nathan Latka

03:25Hopefully not churn. Right? What do you mean what do mean by that?

Ryan Glasgow

03:29So improve churn. Yeah, So improve every point of their conversion funnel, you know, including churn, and actually preventing churn. And so, you know, what we do is with the pilots, and a lot of times even leading up to a subscription, is saying, you know, what does this mean for you? What if we can increase that conversion by 5%? What if we can reduce churn by 2% or 10%? And you can start getting the numbers and actually

03:53model out what the impact is on their business, and actually, you know, well, it'll hold us accountable what we think that we can do.

Nathan Latka

04:00Yeah. You're basically arguing, take the mechanics of how a funnel work. Right? And if you change a... Even a couple percentage points increase at certain things because of how a funnel works, you actually get massive output in terms of value if you improve these things. That's essentially the sales pitch. Is that accurate?

Ryan Glasgow

04:15Yes. That is it.

Nathan Latka

04:16Interesting. Okay. So are you... I mean, give me a general price point. Right? I mean, since it sounds like you have a couple customers here, are you talking kinda $10 a month or, like, $10 a month? Or you... What space do you think you're gonna be playing in? Small, medium, or or enterprise?

Ryan Glasgow

04:28Yeah. We're very focused on the enterprise. I mean, values are an annual basis between 50,000 up to, you know, 500,000. You know, this is really the top of the market. That's where the unmet need is in the market, and that's what we're focused on as a company.

Nathan Latka

04:42Okay. So yeah, so that's it. By the way, congratulations. I mean, that surprises me a little bit that you're able to convince people to spend this kind of money on these things. It sounds like you've done a really good job at actually modeling the value the funnel is losing because they don't have this kind of thing installed. I mean, is that really a one on one kind of coaching call where you're articulating the potential losses? Or

05:01do you have some tool like WebsiteGrader that says your SEO sucks, now pay us to do your SEO?

Ryan Glasgow

05:06Yeah. You know, it is really those one on one conversations. A lot of times we'll get under NDA, they'll share their numbers, we'll know exactly how their business is doing. And then from there, we can dig into specifics and say, you know, what would a few percentage points look like if we move the needle here, or if we made this type of impact on your business? And on our side, it's really around just a spreadsheet and

05:26modeling it out and coming back to them and saying, this is that revenue impact, and here's what we think we can do.

Fundraising: Why Raise and How Much

Nathan Latka

05:32Talk to me a little bit about history so far. It sounds like you have fundraised. Why'd you make the intentional decision to fundraise instead of bootstrap?

Ryan Glasgow

05:40Yeah. You know, with every company, it's really around finding the right talent. And with San Francisco, it's a very expensive place to live. Wanted to really bring on people who, you know, were the best at what they do. I mean, our data scientist has a PhD. He has eight years of experience with AI. When you want to attract the type of talent You're talking Kevin? Yes. Yeah. Kevin and Joe, Joe has over twenty years of experience.

06:04He's our lead architect and came from another AI company down the street from here. When you wanna attract this type of talent, they wanna see investors bought into that vision and that business model. And it really gives a stamp of approval for that. A lot of these people in Silicon Valley to move forward and take that step and join particularly early stage companies.

Nathan Latka

06:22So how much did you end up raising? How much in the company to date?

Ryan Glasgow

06:26We did technically what's called a pre seed. The terms keep changing every couple years. But we did a pre seed right around $700,000 and I put in some money myself as well. And And it was really getting people who were committed to that enterprise story. You know, if you look at SMB surveys and SMB, it's, you know, there's a lot out there. If you look at Product Hunt, you'll see a lot of survey tools. You know,

06:47we're not really focused on that. And so it's finding the right investors we're saying, hey, we actually understand there is an opportunity at the top of the market. It's gonna take a little bit longer to get there, but we believe in you and we really want to invest in what you're doing.

Nathan Latka

07:00Yeah, mean, by the way, SurveyMonkey's been on and I mean, you see a kind of Typeform's bond, which you could argue is kind of in the space. I mean, there are all kinds of kind of whether they're starting off at freemium $10 a month plans. I haven't heard of someone, will say this, I haven't heard of a product like this starting off enterprise. So it's... I'm excited to keep chatting here for another five, ten minutes

07:18to figure out kind kinda the thesis here. And it may... It sounds like you actually saw that opportunity. I mean, this is like a very intentional thing.

Ryan Glasgow

07:23Yes. Yeah. Enterprise space, there are a few customers at the top end of the market in the enterprise survey tooling. And, you know, the challenge though is that if you take the same product like SurveyMonkey, and you add a sales model, and you really bring that to market, you know, the companies at scale have very specific needs, and they have millions and millions of users using their product. And so what does it look like to actually

07:46help run and conduct surveys, and analyze all that survey data at scale across hundreds of thousands or millions of users? It's a very unique challenge that a lot of the small businesses don't face. And so that's why for us, our strategy was entirely at the top of the market for the largest software companies. And we're currently onboarding some of the largest software companies in San Francisco right now who came to us and said, we have, you

08:11know, 10,000,000 monthly active users. We wanna understand why they're coming to our homepage and not signing up, or canceling our subscriptions, or, you know, where we're not meeting their needs with our core product offering. Can you help us do that? And that's really what we're focused on solving.

Nathan Latka

08:26Yeah. No. It makes a lot of sense. I And know you're early, but what it sounds like you've onboarded, what, like, one or two kind of customers today? Are you closer to kind of 10 or a dozen?

Customer Count and High-Touch Success Model

Ryan Glasgow

08:33You know, it's it's it's over a dozen right now. We have a, yeah, a small handful of of, you know, customers that we're working with, and it's really, at this point, just making sure they're happy. Our pitch is that we're an extension of their team. I'm always at their offices. It's great being in San Francisco to just walk over or take an Uber and stop by and ask what their goals are. What are they looking to

08:56accomplish quarter? What are they looking to accomplish in their upcoming sprint cycles? Or what are those questions that are top of mind in their funnel? And we look to take on those and tackle those challenges with them. So serving as an extension of growth teams, product managers, user research teams, you know, whatever those challenges are, we get into the trenches with them. We use the platform that we've built to help solve those challenges.

Nathan Latka

09:17Yeah. Yeah. I mean, by the way, you've got more than a dozen folks, told me a $50,000 ACV earlier. I mean, that puts you over $600,000 in terms of run rate in ARR today. Is that accurate, or were you discounting aggressively early on?

Ryan Glasgow

09:29There were some early discounts, but you know, don't want to get too much into the revenue, but you know, we're certainly on track to end the year in a really good spot.

Nathan Latka

09:38And Do you feel like we can break the kind of the million run rate at the... At that point?

Ryan Glasgow

09:43Yes. Yeah. It... We're certainly, you know, turning that direction, and and it's looking very positive at this point.

Nathan Latka

09:48As you No, come on, Ryan. I'm trying to get you to open up a little bit here. Does that goal freak you out, or does it feel very attainable?

Ryan Glasgow

09:54It feels very attainable for Okay. Yeah. Yeah. For us, it feels very attainable, the contract size. It's typically 6 figures, and the interest and demand that we're getting are from a lot of the top players. And for us, it's really around being able to control the destiny of the company, have the funding. A lot these companies do pay upfront, so it puts us in a very favorable cash position.

Nathan Latka

10:16Yeah. How... I mean, look, getting paid upfront is great. That means you could, on a GAAP basis, stay cash flow positive and and still spend one year of ACV to get the customer. And if you argue that whoever can spend the most to get the customer wins the customer, that puts you in a favorable spot. How are you managing your payback today? Are you comfortable with the twelve month payback period?

Ryan Glasgow

10:36The payback right now, it's less of a focus. We are still early stage. It's really those customer success stories, building out those testimonials and making sure the people we work with are really happy. The economics are starting to... It's starting to think about that a little bit more and ensuring that the margins are there and that we can support the full sales cycle. But that's still early in what we're starting to figure out.

Nathan Latka

10:59What's the team size today? How many people?

Ryan Glasgow

11:02It's a mix of full time and contract, and I've seen certainly a big shift for companies of any size being more open to working with contractors, working with remote workers. We really leaned in that model as well. We're over 10 right now.

Nathan Latka

11:17But three full time?

Ryan Glasgow

11:19It is more than three full time, but the total team size is right around a dozen for us.

Nathan Latka

11:25Okay, good. Sorry, how many full timers?

Ryan Glasgow

11:28For full time we have right around five.

Nathan Latka

11:31Okay, good. Yeah, by the way, I love the contractor model. I mean, I I'm hoping somebody soon, you know, goes public with one employee, right? I mean, that would be that would be amazing because we have some we you know, the the sharing economy allows us to leverage so many global resources to build these things. So I think that's great. Too early to talk about things like gross churn and expansion revenue?

Ryan Glasgow

11:51Yeah, a little bit early for us on, you know, those numbers. And and, you know, at enterprise, when you you do make that commitment is typically a longer time view as well.

Nathan Latka

12:00Let me talk to you about a little bit something different. The the hit on San Francisco is always like, raised too much money. They're doing no revenue. They burn a bunch of cash, use other people's money. It never works out. I mean, it sounds like you're actually driving some nice revenue here with not a ton raise. And the way I like to measure that is is the founders can keep kind of their ARR to funding ratio

12:16generally close to one to one. You hold leverage. You're not gonna get diluted out of the wazoo on your next round. That being said, you want to obviously burn some capital and invest in growth. Engineers are expensive. How do you manage your burn? I mean, I assume you're still burning obviously to drive growth.

Burn Rate and Cash Management

Ryan Glasgow

12:32Yeah. Yeah, Certainly, you know, still, you need to keep the lights on you to pay the team. But, you know, with the contract size, with the customers that we're working with, we're revenue generating with the insights that we create. So we come to these businesses saying, we will actually identify ways for you to increase revenue for your business. We will contribute to your bottom line. And, you know, when we're creating that type of value with our

12:55customers, it puts us in a good position as a business. And so in terms of the burn, you know, it's not something that worried about. I mean, you're right, companies do raise a lot of funding here. I think for us, it's been a very light funding model, given that we're heavily using an artificial intelligence. There's a lot of really interesting innovations that we're bringing to the market in the customer survey space, And you know, the talent

13:18is expensive, but you know, knowing that these contract values and this revenue is helping support that and drive that growth that it's not something I'm too worried about.

Nathan Latka

13:27Yeah. I mean, Ryan, it seems like, are you comfortable? I mean, are you around five k burn, 10 burn, 100 burn per month or more than that?

Monthly Burn Comfort Level

Ryan Glasgow

13:36You know, it's less than 100.

Nathan Latka

13:39Okay. So you're comfortable with anything less than that?

Ryan Glasgow

13:42Yeah. Yeah. Right now, anything less than 100 is fine. And and, you know, early stage, it's not necessarily the cushy salary that I used to get in in previous jobs. But, know, it certainly pays the bills.

Competing Against Point Solutions Like Brightback

Nathan Latka

13:52Last question. There are point solutions, right, for what you've described raising just, again, way too much capital. Brightback is a good example. 18,000,000 specifically for the churn funnel, working with pilots on big enterprise accounts like Netflix. They actually have similar ACVs to you. How do you try and beat these people that are focused on a very specific point in the funnel doing what you're doing?

Ryan Glasgow

14:13Yeah, you know, different companies are focused on, I think, different types of problems, and also be embedded in

14:20you know, in the teams differently. You know, with us, we really focus on user researchers, and helping them actually better understand those customer experiences at scale. And so it's really around how can we have a flexible solution that can actually move around to focus on different problems that companies face. If you look at a large software company, one quarter they'll focus on churn, but the next quarter they'll focus on acquisition. The following question they'll folk... You

14:46know, the following quarter they'll focus on retention or activation. And so for us, building that flexibility into the platform to ensuring that we're continuously meeting the needs and answering the questions that those product teams have.

Famous Five: Favorite Business Book

Nathan Latka

14:58Yep. Very good. Let's wrap up here with the famous five. Number one, what's your favorite business book?

Ryan Glasgow

15:03Business book, Good Strategy Bad Strategy. I think one highly undervalued and underrated concept in tech is strategy. We live in an increasingly competitive environment. Anyone can create a company these days. You need to know how to compete, and you need to know how to win.

Nathan Latka

15:17Yep. I agree.

15:18Number two, is there a CEO you're following or studying?

Famous Five: CEO You Follow and Favorite Tool

Ryan Glasgow

15:22No one in particular right now. You know, I'd say generally enterprise businesses is one that I've any type of enterprise business I've really been focused on, and... But no particular CEO comes to mind.

Nathan Latka

15:33And number three, is there a favorite online tool you have for building your company?

Ryan Glasgow

15:37We have a pretty standard stack right now, and so nothing that would really surprise you. I will say though, that keeping it as simple as possible always is best. And Trello is something that we use at Vurb, in helping build that company, and now we're continuing to use Trello as well. And I think just keeping the tools simple and the information accessible.

Nathan Latka

15:57Number four, how many hours of sleep do you get every night?

Famous Five: Sleep, Personal Life and Age

Ryan Glasgow

16:01Last night, I got around five. I typically wish I can get more, but, you know, it's something that keeps, it's a problem that keeps me up at night, and I'm busy really And excited and it's something that is... It's honestly difficult to go to sleep.

Nathan Latka

16:13What's your situation? Married, single, kids?

Ryan Glasgow

16:16Single right now. Have a girlfriend in Los Angeles.

Nathan Latka

16:18Okay. And no kiddos running around?

Ryan Glasgow

16:20No kids.

Nathan Latka

16:21Alright. And how old are you, Ryan?

Ryan Glasgow

16:2331.

Nathan Latka

16:23Last question. What do wish your 20 year old self knew?

Advice to 20-Year-Old Self

Ryan Glasgow

16:2720 year old self.

16:31I think it's really around continuing to... You know, I I think early on, I joined a lot of really early stage companies. A lot of times they're the idea phase. I took some big bets. And, you know, I think that's something that, you know, has worked out for me. I think that isn't always true for a lot of people. But even if those ventures did not work out, and they did flop, they, you know, did fail, I

16:57think it would be, you know, it's just a rewarding experience. And I think it is really staying big picture. Keeping in mind that you know, the things that don't work out actually become the best learning lessons, and always keeping your head up.

Nathan Latka

17:11Guys, there you have it UserLeap working with 12 enterprise customers helping them understand at different parts of the funnel, what questions customers are asking really with the goal of increasing but you know, percentage points here or there, whether it's preventing churn, increasing trial to conversion, etc. Again, 12 customers pay on average call it $44,100 per month, about $50,000 ACV. So call it $50,000 a month right now in revenue with a million in sight. Hopefully this year, we'll

17:35see what happens $700,000 raised to date five folks on the team too early to talk about the other economics. But Ryan sounds like you're growing fast, man. Thanks for taking us to the top.

Ryan Glasgow

17:43Alright, thank you.