8 Product Hurdles Every Founder Must Clear — This PM-Turned-Founder Shares His Playbooks

8 Product Hurdles Every Founder Must Clear — This PM-Turned-Founder Shares His Playbooks

Repeat PM turned first-time founder Ryan Glasgow addresses the tough product questions every founder faces, from segmenting the market and iterating on early MVPs, to finding product/market fit and spinning up a second product.

Narrowing in on a market and finding the right customer. Building out the first version of the product. Teaching yourself how to bring it to market. Trying not to get lost on the journey to product/market fit. Sticking to a consistent vision, even as you eye new markets and product ideas.

These are just a few of the challenges that pave the path of the PM-turned-founder. Ryan Glasgow knows it well. He started his career as the founding product manager at five different startups, including Vurb (later acquired by Snapchat) and Weebly (later acquired by Square). It was in these roles where he spotted a gap. Release cycles moved quickly, but getting high-quality research was a slog — from the struggle to find participants and the pain of getting ghosted in interviews, to waiting on an overtaxed in-house research team at larger companies and wishing he had one at smaller startups.

So in 2018, he left the life of a serial early-stage PM behind and set out to build the tool he’d always wanted. As the founder and CEO of Sprig (formerly UserLeap), Glasgow and his team have created an all-in-one product research platform that helps PMs, user researchers, and growth marketers launch microsurveys, test concepts, and conduct video interviews to uncover customer insights faster.

As seed supporters of Sprig (and users of their product — see if you can spot it in action in our newsletter), we here at First Round have had an inside look at the product’s journey from a PM’s idea on paper to a tool used by more than 500 customers like Dropbox, Adobe, and Loom.

In this exclusive interview, Glasgow takes us through that trajectory, tackling the tough questions product builders face in every stage of getting a startup off the ground. We start by rewinding the clock back to the 6-month period before he started the company — when he was validating his idea and assessing the crowded market. From segmentation and initial customer conversations, to iterating on early product versions and surfacing feedback, Glasgow shares the tactics and questions he leaned on most in his 0 to 1 days. He also outlines the consistent mistakes that founders tend to make on the voyage to product/market fit, digs deep into how he approached pre-Series A founder-led selling, and offers up advice for expanding beyond the initial product. Let’s dive right in.


For PMs with the itch to take a spin in the founder’s chair, the first step is coming up with the big idea. “I joined Weebly as the first product manager because I really wanted to experience that hypergrowth phase and work with a larger user base, having previously only worked in that 0 to 1 space. After helping to scale the company from around 40 to 300 people over a three-year period, I was burnt out and needed a break, so I left in 2017 and took a year off to travel. And part of the goal was to really explore areas that I didn't quite know as well,” says Glasgow.

“I started to look at the shift from the downloadable files to cloud-based documents. When I first tried Figma, it really clicked for me that if downloadable design files can now be fully cloud-based, then this is a pattern worth exploring,” he says. “But as I started to experiment in that space, I got a little bit stuck getting that company off the ground and realized that it wasn't working.”

That’s when Glasgow came across a book that shifted his perspective: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services. “Anthony Ulwick really breaks down the process of thinking through the outcomes that customers are looking to solve,” he says.

The cliff notes version is to start by looking at the broader market that you're trying to serve, collecting all of the outcomes that these target customers say are important in a solution — essentially jobs-to-be-done. With those 20-40 outcomes in hand, get a set of customers to measure them against the two dimensions of importance and satisfaction with solutions they use today — the important items that are unsatisfied are your sweet spots of underserved opportunities.

For Glasgow, this was impactful in two ways. “One, I realized how powerful surveys could be — because the book was really about using the survey based approach to bring innovative new products to market without even writing a line of code,” he says. “But two, it helped me uncover and think more clearly about an even bigger space than cloud-based collaboration, which was helping other companies better understand their customers.”

If you're struggling to come up with startup ideas, start by thinking around the needs of a group that doesn't have a solution that uniquely achieves the outcomes they're looking for.

With a new specific idea in sight, Glasgow talked to a broad set of product managers, researchers and designers about what a product development team is looking for in a qualitative research solution — and unsurprisingly, several outcomes bubbled to the surface. “Maybe it's insights delivered in 24 hours. It could be something like having survey creation or data analysis done for you because you don’t know how. Or a systematic way to reach out to customers without having to go to a database,” he says. “I found that these were all really important outcomes to these teams, but they were highly unsatisfied with the existing tools on the market — so this was a market that was underserved.”

With his course set, Glasgow looked ahead. “It was a set of very ambitious outcomes, and I knew it would take some time to build and develop the product to achieve them,” he says.

Photo of Ryan Glasgow smiling
Ryan Glasgow, founder & CEO of Sprig (formerly UserLeap)


Of course, the surveying and product research space wasn’t a new category — in fact it was a market that looked rather crowded. To convince investors, he’d have to go many clicks deeper than a “We're going to create a modern surveying tool” pitch.

“I saw all the tools out there and was familiar with traditional survey platforms,” he says. “But if you look at their own stories, many of those companies were started over 20 years ago now. And what was really innovative about those technologies was bringing that offline survey online. At the time, that was a very key innovation. But since then, we now have this rise of continuous deployment and development,” says Glasgow.

Figuring out who to build for:

“When I did the market segmentation and looked at the needs of this specific audience of product managers, I saw this huge opportunity of an underserved market — and one that was growing really fast,” he says. Part of this work also entailed tapping into his own experiences as a repeat-PM. “Many entrepreneurs will start a company to solve their own challenges or pain, and this is exactly one of those stories,” he says.

“When I looked at my own experiences and I talked to other founders and PMs, 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 provided to the product manager to empower her decision-making. But thinking back to my experience as a product manager at companies like Weebly, I didn't feel like there were any solutions on the market that were built to solve the needs that I had. I didn't have a great toolset or platform to really communicate with customers in that systematic way,” he says.

Figuring out where to play:

But a research tool for PMs wasn’t targeted enough. “When I did the segmentation, I saw that the most underserved product management market segment was actually with the larger companies.” This also tracked with his own experiences. “When I think back to the first four companies that I helped build, there was honestly less of a challenge around qualitative data because you could almost talk to every customer at that size,” he says. “But when I thought about my experience at Weebly, where we ended up with 50 million accounts by the time I left, I saw this incredible challenge of gathering and understanding customers at scale.”

Glasgow notes that waiting for research results at this scale wasn’t always possible with a team that was shipping every few weeks — on the other hand, a lack of training and know-how meant he was hesitant to conduct tons of research flying solo, for fear of introducing bias or walking away with the wrong conclusions.

Figuring out what they need:

But there was a more specific challenge as well. “It really dawned on me when I was talking to these at-scale companies with user research teams: Product managers were looking for a solution that made that qualitative data much more accessible. Because at these larger companies — and I'd experienced this at Weebly — the user research data was very valuable, but it was often delivered in slide decks,” he says. “And anyone in product today strongly would prefer data to be delivered in a platform or a product where they can really explore on their own. Looker is a great example of allowing the decision-makers to explore the data so that they can then form their own conclusions and conduct their own analysis.”

In short? “When you think of segmenting around 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 they were looking for. So the premise and hypothesis around Sprig was that the underserved market is not only in the product management space, but was even narrower in the high-growth to at-scale companies segment. From day one, we set out to build a solution that specifically meets those needs up market, and nothing that I had uncovered in my competitive research was built for that specific segment,” he says.

Any time you enter what many feel is a commoditized or mature space, you really need to think through your product strategy and market segmentation to find where that underserved opportunity is — that’s how you can build a highly differentiated product that uniquely suits a specific customer segment.


With a specific product thesis and an ideal customer profile in mind, the next hurdle is figuring out exactly what to build. There are endless feature combinations to configure, and potential jobs to stack rank. As someone who’s in the surveying and question asking business, it’s no surprise that Glasgow approached this task in a methodical and intentional way. Here, he walks us through his early customer discovery conversations, and importantly, how he spent that precious time in front of prospects.

Keep it cold.

“I started to hypothesize and design with mock-ups and really a lightweight sales stack showing this product,” he says. “One of the key learnings I had early on is to never involve people who you personally know in the customer development process. Folks often reach out to their own audience for customer development — an extreme example might be Gary Vee — but I think it’s often misleading. Instead, I started to cold email founders and PMs at Y Combinator companies. I had no relationship with them, and I wanted to see if they would respond to my emails, because if I'm truly solving a pain that they're experiencing, then they will spend time. And I was able to get several of them to respond and take meetings with me.”

In the very beginning, I really wanted to test and validate whether this was worth working on by seeing if people who I didn't know were willing to spend time with me to help co-create and develop this product.

Glasgow notes that this is particularly important for B2B endeavors. “Time is more valuable than money if you're selling to someone here, 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,” he says.

He shares an example of some early potential customers who were willing to sink in that time as design partners. “There was a PM at Hotwire, for example, and over the course of 12 weeks he spent probably close to an hour every week co-creating and providing feedback. And this is someone who I didn't know at all,” says Glasgow. “There was a PM at Intuit on the QuickBooks team as well who spent time providing feedback on those mock-ups and the deck that I had created. And so I started to validate that people I don’t know in this product management segment at high-growth and at-scale companies were willing to spend time and provide feedback, because it resonated. It solved a problem that they were experiencing in their lives because the existing solutions for them were, in fact, broken.”

Stay focused on your outcomes and your segment.

More tactically, here’s what those early meetings looked like: “I had a deck with the screenshots and a list of the different outcomes and features that I was looking to build. And every week we would meet and I would just show the progress around the product direction. In the Hotwire example, we did some demos with his team, but we were very early in our journey and we didn't have a security posture yet, so it ended up not being someone who turned into a customer. Instead he was providing that feedback along the way, saying, ‘Hey, this isn't really resonating for me,’ or ‘I like this feature that you designed, or this feature that you're telling me about.’”

Glasgow brings it back to the outcome-driven innovation framework that unearthed the original idea. “It tells you the outcomes that are important to the audience and 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,” he says. “And so it was really through the iteration of working with potential Sprig customers, testing, sharing, and showing them these mock-ups of different sets of functionality and features on a weekly basis, that I was iterating on how to actually solve those outcomes.”

You can't rely on your customers to figure out what to build. They can really only tell you what outcomes they're looking to achieve

He also stayed laser focused on his segmentation work. “Given that the underserved market was the high growth or at-scale companies. I found it to be incredibly important to only work with companies in that market. And so when I had those early conversations, I actually kept it to a very small set of customers,” says Glasgow. “For example, through the Weebly connection, I was able to start working with Square and other early customers like Plann and Thunkable — they all had a user base of at least 500,000 users using their product on a monthly basis.”


With a sharper understanding of what customers are looking for, it’s time to build. Square one is sketching out the must-haves in an MVP.

“Given that it’s 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 first vision of Sprig was only the SDK. It was a piece of code that these companies could add into their product,” says Glasgow. “And there was a place to log in to view the raw data responses, but everything else was completely manual by myself and the early team. And so if you wanted to launch a survey, change a survey question, stop a survey, choose where that survey appeared in your product — we were doing all that ourselves. We’d go into the product and change the code, and then through the SDK that was installed in the customer’s product, we would update all the configurations and then it would update the SDK and what was actually being displayed in their product.”

Data analysis was also a key outcome for Glasgow to deliver on. “On a weekly and monthly basis, I was building out decks and analyzing the data for them. These early customers were getting me as their product manager and researcher, building decks saying, ‘Hey, I looked through 2000 survey responses and I've analyzed everything for you,’” he says.

“Through all of these manual interventions and a consultative approach, I was able to see what was clicking and where the positive feedback was, so we could focus our development efforts on those areas. We started to hire a PhD data science team, brought in engineers who had built infrastructure at scale, built out custom surveys and introduced dynamic targeting,” Glasgow says. “And these were all features that took at least a year to build because they're incredibly complex at scale.”

By doing everything manually at the beginning, it allowed us to really validate the product that we were building was solving those outcomes that we had originally set out to solve.

Of course, this do-things-that-don’t-scale approach is high-touch, and can present something of a trap. “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 were doing manually. It would just take resources,” says Glasgow. (We’ll note that Looker pursued a similar consulting-esque model in their early days.)

What’s more is that this approach proved doubly useful in Sprig’s early fundraising conversations. “In conversations with investors we could say that we're delivering key insights for these customers in unique ways, and 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,” he says.


As Glasgow wrote in a blog post way back in 2013, of the startups he’s helped launch, “the most difficult task has always been to take an alpha product and iterate until it begins to find traction.” Turns out that still holds true in 2021.

The key to unlocking this traction requires — you guessed it — talking to customers to get their take on what you’ve built so far. Here, Glasgow shares advice for getting more out of your own product feedback conversations with customers.

Treat customer development calls like a 1:1 with your direct report.

“The main goal early on was to help us understand what is or isn’t working here. I treat customer development as a one-on-one with a direct report — you just want to ask the hard questions,” he says. (Or as Review favorite Julie Zhou put it, strive to make sure that all your 1:1s feel a little awkward).

He shares some examples of his go-to questions:

  • What are the highs and lows with our product right now?
  • I was meeting with the head of product at one of our largest customers the other day, and right on the call I asked him, “Zero to 10, How satisfied are you with Sprig as a company? And help me understand what we could do to get you to a 10?”
  • What's one feature you wouldn't be disappointed if we removed?

But for Glasgow, it’s more about the “hard” part, rather than fixating on particular questions. “I don't think it's necessarily about asking super innovative questions. It's really just digging in and asking the tough questions to make sure that customer really cares and that you're learning both the positive — and, more importantly, the negative — about what you've built so far,” he says.

Invalidate ideas quickly by asking the tough questions.

This might seem obvious, but in his experience, many shy away from it. “At the first startup I worked at, I went to the founders and said I wanted to ask the product/market fit question. And they honestly said that they didn’t want to know. And I thought to myself, I'm spending all this time at this company and we don't want to ask the tough questions. You have to lean in to ask those hard questions. Otherwise, why are you there? Who are you building for? If you're not willing to ask those tough questions, there's a good chance you’re wasting your time, because you're probably going in the wrong direction if that's uncomfortable for you to ask.”

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?

The hard questions in customer conversations also correct for another common tendency. “Everyone leans into their own intuition far more than they should. I have worked with founders where there is strong intuition around building a product or a feature and bringing that to market, but there was no real user research process and no difficult, uncomfortable questions were asked very early on,” says Glasgow.

“I recall at one company where the founder had very strong intuition around bringing a new feature to market. It took a team of four people a year and a half full time working on this feature. And we actually didn't even launch it. We launched the landing page for the feature, which we linked to from the homepage. And no one clicked over and opted in to even try that feature. Here we are, weeks away from launching after a year and a half of work — and we just shut it down. And it’s a shame, because there are just so many ways to invalidate an idea by posing those tough questions to actual customers whom you hope to serve with those features.”

A great outcome for any business, 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.


With an early version of the product out there in the world, the next phase is proving out that people want to buy it — the elusive early traction that signals you’re really onto something here. In Glasgow’s experience, this is where things tend to get painful.

“One of the frameworks that is really popular right now is measuring product/market fit. I've seen founders spend years building, iterating and measuring product/market fit, trying to understand how to get there — and they get stuck,” he says. “If you take a step back to see the origins, it was Sean Ellis who pioneered the survey. And he was a marketer who was looking to join startups that already had products that customers loved. And so he used that question of ‘How disappointed would you be if you could no longer use this product?’ to validate whether companies had product/market fit. What I recommend to founders today is using a different framework for discovering product market fit,” says Glasgow.

Founders should recognize the difference between validating product/market fit and discovering product/market fit.

“Because as a founder, if you're only validating whether or not you have product/market fit, it could take you five, 10, 20 years of testing a hypothesis and only measuring your solution.”

As Glasgow has previously written, in his view it’s important to measure the severity of the problem you’re solving and your customers’ level of interest in solving the problem — customer/problem fit, if you will. In short, it’s about continuously iterating on your customer profile and the problem you’re solving (as Glasgow discussed in the sections above).

“Using the outcome-driven innovation framework is a great way for founders, particularly early on, to discover product/market fit,” he says. “In Sprig’s case, I thought that if I can build a product that delivers on this set of outcomes that are important to this audience of product managers, designers, and researchers, then that was really the definition of product/market fit before I even had to really build the product.”

If you can deeply understand what your customers are looking for, you can discover product/market fit without actually having to build a product.

Now with the product up and running, Glasgow and team ask the classic questions to validate whether they’ve hit that product/market fit benchmark of 40% of users who say they would be "very disappointed” without the product. “Right now we're running the product/market fit survey in Sprig to validate whether we have it, and the good news is that we do,” he says.


Okay, so this isn’t a product challenge in the strictest sense, but for product-focused and technical-oriented founders, figuring out sales for the first time can often be something of an Achilles heel. Going from an initial handful of early customers to a repeatable, fine-tuned motion has been the death knell of many a startup.

“Prior to Sprig, I’d never worked at a company that had a salesperson. But when I identified this underserved market of high growth and at scale companies, I knew that it would take a sales approach,” says Glasgow. “We didn't publicly launch until December 2020 — and I was still meeting with every customer who paid us any money until we started our sales team about eight months ago. That approach allowed us to build a strong foundation and really develop both the sales process and my own sales skills up until our Series A.”

Fresh from the founder-led sales trenches, Glasgow shares the tactics that made the biggest difference as Sprig went from zero to over 500 customers.

Submarine to reduce the pressure.

“Anytime I don't know how to do something and I get stuck, I immediately jump right into books. I read probably six or seven books on B2B sales, as well as a lot of articles online about how other founders made the shift. The book that really helped me understand how to sell though was ‘You Can't Teach a Kid to Ride a Bike at a Seminar,’” says Glasgow.

“It's an older book, so it'll feel a little bit outdated. But it really had a lot of breakthrough concepts for me. 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,” he says.

In every conversation you have, you never want to create this situation where a prospect feels like they have to make this big decision on the spot.

But how can founders deflate the pressure in these customer conversations — especially in the early days, when it feels like every potential deal falls into the make-you-or-break-you category? “One of the tricks that I learned is that at the beginning of every meeting you have with a potential buyer or someone who might use your product, always let them know the decision they need to make at the end of the meeting. It’s called submarining — you're breaking up this long, really big decision of whether to potentially make this annual or multi-year commitment to your product into mini decisions,” says Glasgow.

“And so perhaps on that first call with a prospect who responds to your email, start by sharing a little bit about who you are and say, ‘By the end of this meeting, I’d like to know X, and I'm going to ask you if you'd like to set up a follow-up demo with me,’” he says. “That way everyone understands the goal of that time together. They're not buying something. They just need to get to that yes or no decision. And a no is totally fine and actually encouraged if they don't want to move on.”

Make each sales meeting a contained decision. What are all the questions and information that you need to provide to that prospect to help her reach that decision?

Refine your playbook.

With that approach in mind, Glasgow moves on to explain the key activities of what that selling process looked like on his end.

“If you're starting to see traction with a couple customers and you're looking to accelerate and bring on more of them, the first step is to look for ways to get that repeatable set of opportunities on a weekly basis. For us, a lot of it was filling up the calendar with these meetings with product managers and user researchers in our segment,” says Glasgow.

“You might want to hire an SDR to help develop these leads. Perhaps you want to rely on your investor network to help provide those opportunities — with Sprig at the time we were often relying on customer intros from the First Round team and our other investors. Perhaps you have your own network, although again, that's often not recommended given that established relationships can lead you in the wrong direction,” he says.

The next step was validating that these leads fit his target customer profile. “It was quickly qualifying or disqualifying these conversations, seeing if Sprig could solve a product or business challenge that they were facing today. You want to see the consistency of who you sell to. Who is that ICP?” he says. “For the product managers or researchers who we could help, they were facing challenges like onboarding drop-off, increasing churn with their subscription, or finding ways to drive product adoption,” says Glasgow.

“Then we'd often move into a trial phase. I didn't even talk about pricing or try to sell them anything. It was really about getting them set up and having them install our SDK into their product, often before a contract was even signed,” he says. “As a product manager and someone who didn't have sales experience prior to this, I really thought, ‘Let's let the product do the selling for me.’”

Glasgow walks us through a real-life early customer example to illustrate what that founder-led sales process looked like. “I got an intro to the growth product manager at Code Academy. I set up a demo with him, showing him the product and talking about some of the areas he was looking to uncover. And from there started to get him set up an account with us,” he says. “So in that second meeting, I created an account for him and started to pick out those templates from our template gallery that I thought could solve the challenges he was facing at that time — again, solving the problem in that consultative way. By the third meeting, I let him know the exact steps to install Sprig into their website, and they went live and were quickly able to see the data and the analysis.”

Of course, there are several steps in between lead generation and inking deals. “Once you start to find that repeatable way to develop those conversations and initial discovery calls, it's about starting to develop that playbook. For every meeting, I recommend starting a Google Doc and writing down an outline for what you think that sales process is right now. After every meeting, write down what's working and iterate to remove the pieces that aren’t working,” says Glasgow.

“I started with one way to sell the product, but for nearly all of 2020, I was constantly adapting it until we got to what we have today. Right now the playbook is so repeatable that we’re growing our sales team and anyone really at Sprig can look at what I did last year and replicate that.”

Here’s what’s in Glasgow’s doc: “What we have is all of the meetings that are required to get to the contract signature. Within each meeting, it outlines the questions to ask, the main topics to cover, and the decision that needs to be made with the prospect at the end of every meeting to continue on to the next meeting. That way you know where you want to be in the process.”

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.


With product/market fit and a well-oiled GTM motion, it’s natural to start looking to the horizon of what’s next — the newest features, capabilities, or even entirely new product lines that you can introduce to take your company to the proverbial next level. But innovating while scaling the existing product is a highwire balancing act. To further mix our metaphors, the new bets you place don’t always pay off, and choosing an adjacent sandbox to play in feels somewhat like starting the startup ideation process all over again.

Here, Glasgow shares his advice (which is particularly fresh, given that just this week Sprig rolled out new concept testing and video interviewing capabilities).

Lean on this framework to find ancillary — not tangential — jobs.

“When bringing new features to market, it still comes back to talking to customers and understanding what they are looking to achieve,” says Glasgow. “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 maybe you're not doing exactly what that other vendor is doing, but you have to think about how your company can build something that actually solves that same job or that outcome in a way that's both unique and authentic.”

Glasgow offers up a specific example: “Figjam is a great example from Figma — they're taking this concept of virtual white boarding and they built a feature around it. And I'm sure they saw that a lot of their customers were using Figma for high-fidelity design and prototyping, but that for the ideation phase in design, they were using other vendors. There's a lot of virtual whiteboarding solutions out there, but they likely saw that there's such a high attach rate to Figma with other virtual whiteboarding solutions like Miro or Mural that they could think about how to uniquely solve this outcome of this ideation and discovery process in the design phase so that designers don't have to switch tools.”

If you’re hunting for your own promising patch, Glasgow offers up this advice: “There's typically about eight different steps in the customer jobs flow of someone starting and completing an action. You can really apply that framework to any product that you're working on and look at the steps that you're solving today. Look at the steps that you're currently not solving and think about how you can solve other jobs that are ancillary to your core product.”

When you find product/market fit for your first product, you have to hit that next phase of growth. What’s that next job you can solve for your customers? Unfortunately, I’ve seen many get this wrong by building something that’s tangential to what they're doing today.

Glasgow shares his thoughts on avoiding this trap.“There are a few fundamental rules that I think are really required to expand from a single product to multi-product,” he says.

Rule #1: Look at the category that you're currently in.

“If you’re not sure, look at how a company like G2 Crowd is mapping and defining different categories. We are in the research category and there's a lot of different jobs that our customers are using Sprig and other vendors for to solve various qualitative insight jobs that they might have to build better product experiences,” says Glasgow.

“A lot of companies might build in one category, but then look to expand into other categories. That’s typically where I see the failure. Consumers today, they look to really buy vendors that solve one type of need,” he says. "An example of this is perhaps Intercom. They started out with this really great chat product, but recently, they've focused on engagement around guides, tool tips and walkthroughs. That's more solving a product manager's needs, whereas their core product was in the customer success category. I believe that perhaps a better path would have been if they had focused on the customer success category, building out other jobs and moving up market.”

Trying to span multiple categories and build a platform that is serving multiple buyers ends up diluting the offering. When you move up market, you need to serve one buyer, but continue to build a platform that can cater to the more sophisticated needs of that buyer.

Rule #2: Revisit your segments and swim in the other direction.

“The second rule is about really looking at the market segments. So at Sprig, most of our earliest customers were all high growth or at-scale companies. And now we're really focused on building for all market segments — small, medium, and large. So we're actually moving down market in many ways,” says Glasgow.

“And so I'm now looking at the different jobs and outcomes of our customers that span all market segments,” he says. “If you're in the inverse position as a company that started with SMB and is looking to move up market, then it's about looking at the features that your customers use today, but then reaching out to those larger buyers you want to serve in your current category in order to understand their needs. And that's when you see companies like Datadog have this explosive growth — they were able to grow as their customers grew and now enterprise is one of their largest customer segments.”

Rule #3: Sink your teeth into the strategy

Glasgow steps back from this second-product-line spitballing to make a broader point.

“The ability to continue to grow and scale a business and win in any market is key for every founder today. A book I recommend here is ‘Good Strategy, Bad Strategy,’ It goes over examples like Southwest Airlines or Ikea, and how they've built this defensible strategy, 20 or even 30 years ago. And that's because they have a fantastically thoughtful strategy,” he says.

“If you look at all the funding that's happening right now, all the new products that are launching every day on TechCrunch and the emergence of low code development, every year it gets easier and easier to bring a new product to market. And once you see that traction, things start to take off. That’s why product strategy and company strategy is one of the most underrated skill sets right now.”

It’s so easy to bring a product to market now. If you didn’t start out in a competitive landscape, you're quickly going to find yourself in one.

This article is a lightly-edited summary of Ryan Glasgow's appearance on our new podcast, “In Depth.” If you haven’t listened to our show yet, be sure to check it out here.

Cover image by Getty Images / Simona Balconi / EyeEm.