This Is How I sold my product to 40,000 companies

In this interview, Matt Martin explains how Clockwise's monetization path, from consumer and business distinctions to enterprise expansion and evolving product market fit. Readers will learn how the discussion connects that problem to concrete decisions about customers, product, teams, and growth. The conversation offers practical guidance for founders and operators on testing assumptions, responding to evidence, and choosing the next step when the path remains uncertain.

My name is Matt Martin. I am the co-founder and CEO of Clockwise. We are a time automation platform that helps individuals, teams, and companies get schedules that they love. Sometimes we land in five people companies. We land in a company that might be 500, 1000, 10,000 and Clockwise starts to grow inside that company, and it allowed us to mature into places where like Uber, Netflix, Pinterest, Instacart, where we have these large deploys that are powering a huge component of their organization. That continues to be a huge driver for us today.

So if you think about monetization, one of the first things that you have to ask is the really basic level is, is this consumer or is this business? I've seen companies make this mistake before where it's a business product, but they're selling to individual end users and ends up looking a little bit more consumer. And the reason I draw that distinction right now is because individual users or consumers are really cheap, and they're pretty bad at valuing their time.

And so in a consumer world, if you're purely consumer and you're selling software, you need a huge, huge, huge volume of users in order to convert a small subset of them to a pretty low price. If you're in a business environment and you're actually talking to somebody who is rational about the value of the product and can reason about it and understands the value, you can charge a pretty fair price for that.

That's more attractive. But and this is where the pitfall is, if you're in a business environment, by just selling to kind of the prosumer end user in a business context, you can end up being more consumer than you think. And now you've really constrained yourself because you're selling to a much more limited audience. It's not just a broad, huge swath of general consumers.

It's a specific context of business usage. But then also those users are still cheap and bad value product. So you have to look at ultimately, does the purchase get a is the purchase going to be made on a corporate card, or is it going to remain on a personal credit card? And I think that starts to define a lot of the parameters of how you think about monetization.

And from there I can go way deeper. But that's the base level that you got to ask when you're thinking about pricing and packaging your product in the initial phases, I would say just don't reinvent the wheel. Your try something that you see from a competitor in terms of their packaging. If you respect them, you like them.

You could probably get a meeting with them to ask them, but the odds are they've thought through a lot of this. All of us have thought through this endlessly, and we and you end up having to price and repackage constantly as you learn new information. But if you can go find somebody that pattern match off of that you think is like pretty good at it, that's a great place to start.

You're going to end up iterating, you're going to end up revising. But don't reinvent the wheel from the outset unless you have really good reason to do so. There's a reason that in the SaaS software space, especially the product line growth space, you end up seeing free personal team and enterprise because there's a progression there of how the product grows and there's a progression of the buyer in free, you know, the buyer, you're just trying to utilize those users in order to grow the possible additional user base.

In personal, you're kind of in that early phase in that possible downside false signal where you're getting individual users that are willing yet to pay a lot for the product, but you do want to monetize them because they end up supporting you to further your journey on that team and enterprise plan. And they get a really good signal about where your power users are at.

But if you're bread and butter is that personal plan, you probably have a long term problem and then you can press up to the team. And there you start to get interesting. Now you're talking to people who actually are seeing team wide value in a company context, because if you're buying multiple sheets, that's not going on a personal card.

As nice as a person as I may be, I'm probably not buying 5, 10 seats for my colleagues. And so now you're firmly in a business context, and you can talk to somebody who's thinking about that team level value and then an enterprise. You're now talking about a larger purchase, either at the department level, maybe even organization wide level.

And that's where, regardless of whether your product line growth or whether you're direct sales, most companies that's going to end up being by revenue the majority of your revenue. It's just those large deal sizes end up becoming what drives a lot of your revenue growth. It's much, much easier to go from 5 million to 10 million or 10 million to 100 million off of 100k, 1 million deals than it is by rolling up a lot of smaller deals.

But so you're in a plg company, monetization is always going to look like a huge kind of winnowing acquisition curve where you have all those free users, some of them pay, some of them get to team, but then a bulk of your revenue gets made up by those enterprise sales. So you got to think through whether you're monetizing.

What are the dynamics that allow you to continue to push up that curve while still maintaining growth? In the early days where you start the company, you're thinking about this moment where you're going to have product market fit, you're like that old mate. That'll all get easier. The reality is that product market fit is not static. And so you have to constantly ask, do I have product market fit?

Do I have product market fit with this larger audience? Do I have product market fit such that I can go up the tier two and enterprise tier? Is there a problem there? And so I would really advise founders to get away from the thinking that product market fit is going to be static. There is a question of do you have fit right now in this moment with this specific market that's going to change over time?

But for us, in terms of timeline, we went from founding the company and getting our early seed round in 2017 to feeling like we had some product market fit around when we launched in 2019, because we were starting to see that compounding growth, we were starting to see people come in. And again, there was a market fit with an early adopter crowd of software company employees, but we hadn't.

And then from that 2019 launch, we did monetize. We did start asking people to pay for the product until 2021. So there's a two year bake period and then 2021. We turned on that modernization engine, we went from 0 to 100 K very quickly. We went from 0 to 1 million. In a matter of months. We went from 0 to 5 million plus in a year, maybe a year and a half.

Because of that initial period where we were acquiring users, we were able to spin up and move pretty quickly on that monetization growth curve. However, word of caution is that's not a reason to monetize late. I think it actually created some little pockets and bubbles inside the company that were difficult to iron out at higher scale. That would have been easier had we monetize earlier.

Clockwise. It was a little bit strange. We're primarily a product led growth company and we are free for a very long time. We are free for too long. That's actually one of my lessons. And we had built up this large user base that had grown very organically and rapidly. And then we turned on monetization of the paywalls, and then we started to charge.

And so that initial 0 to 100 K million up was pretty rapid for us. And I think the lesson in terms of when to monetize, when to price, when to start asking people to pay for us doing this at a later stage where we already had a large user base, it created some wrong signals to the business that growth in revenue was so rapid, it was so exciting that we started to plot ourselves along that curve farther ahead than we should have.

We also let some things ride that would have required more attention had we priced earlier. There are mechanisms in our paywalls that were just off. They were creating weird circumstances, but there were so much revenue coming in the door that were like, not a problem. We're not going to fix it right now. And so it's nice to say, in retrospect, I'm sure a lot of people would like to have that problem, but I think that we should have priced earlier and paid attention to how that pricing worked and the incentives and dynamics that it created in the business, so that we can sustain the longer turn growth a little bit better.

We had to redo a lot of that at a later stage where we had a lot of paying customers, and that's more difficult to pull off for SaaS companies that are thinking about when to price and when to monetize. There's no single right answer, but I would say that the default is the earlier the better. At the very least, you should always be highly attuned to asking the customer what they would pay and then discounting that a fair amount because people will be nice and they may not pay you.

But the reason I say it early is because there's just no replacement for putting up a paywall and asking somebody to put down their credit card. You get so much signal in terms of do they actually value the product? What features do they value? What's the price point that they're willing to hit? You can have conversations with that customer that you weren't able to have before, because either they're not converting and you reach out to them.

And in the early days, I think it's it's so information rich, getting that information and putting it back into the business is insanely valuable. So I would say that, you know, after you feel like you have a product that is viable, like minimal viable product, some people are seeing value that you put up pricing and even a paywall pretty shortly thereafter.

The most important thing by far is to stay connected. And who buys your software and understand their pain points. It's advice that's so common that it's almost trite, but it's incredibly true. When you think about the SaaS ecosystem, what's different about it than a consumer ecosystem is that you largely get to define a subset of who you're going after in the business sphere and build a close connection with that buyer, because depending contract size, there's a concentration of power in a relatively small set of buyers.

And so as you think about your market definition, as you think about what product you're putting to market and who it serves, whether it's an end user or whether it's a department, whether it's a specific executive, you got to go build a relationship with who buys that software and really understand what keeps them up at night, what gets in their way, but also how do they work?

How do they spend their time during the week? What conferences do they go to? What gets them fired? What gets them promoted? If you can understand that deeply, you have better odds of success, not only because you can build a better product because you really understand your buyers problems, but also those relationships that you build will pay dividends over time as you're developing new products, as you're trying to go to market, as you're trying to market your product into the right ecosystem.

And so that would be my number one piece of advice, really get to know and understand your buyers. For us, this is a product led growth company. We're always highly attuned to how the companies that enroll over the long term. And so we look at things like decisions like pricing, packaging, monetization, those are even highly connected with our growth strategy.

And what we look to at Clockwise is making sure that features that are high growth are accessible and usually free. You know, if you think about a plg company, really all that you're doing is you're taking customer acquisition a bit away from marketing and pushing it onto the product, and it still has cost. You've got to develop those features.

You've got to support that customers that are using them. But that is your acquisition engine, and that's where you're putting your money in order to acquire users. And so for Clockwise, that means on the free product, we always look for the features that are driving growth and and push those forward in onboarding to make sure that people are engaging with them, to make sure that people are activating towards them, and then making sure that they're highly leveraged in acquiring other users.

And it'd be highly tactical for a moment. Largely how we do that is using the surface area of the network of the calendar in order to acquire more users. So if you have focused time and you're on a free plan, it's going to have a little bit of branding that says buy Clockwise so other people see it.

If your free and you use our slack sync, your status can be updated automatically, which is awesome, especially in a hybrid environment. But it's going to say buy Clockwise. If you're on that free plan, you send out a link to schedule time with somebody. It's going to say buy Clockwise. We're making sure to use that surface area in order to acquire that next user.

I think the biggest mistake that a fighter can make is collapsing their personal value with a company's value. Like this thing, when it is a journey, it's a wild ride. Sometimes it goes like nuts and you know it's everything you dreamed. Other days it's just like a nightmare. You're battling something that you never tackled before. Your question why you got into this?

And if you're attaching your personal value to that roller coaster ride, it's brutal. And I've seen a takedown, some founders where it's just, you know, it becomes unsustainable. It's really hard. And the last thing you want to do is tap out because you're not managing your personal psychology. And so I had some advice from another co-founder earlier today who had been on this journey, and he said to me, it is a long journey.

If you're traveling on the open seas and you're going through wave after wave, the distance traveled is much longer than if you can calm those seas and just continue on path. And so I think a lot of the advice that I give to founders is pay attention to that personal psychology, because if you can manage that, it makes everything else easier.

Giving advice to other founders that are looking to grow their company. My first piece of advice would be, which is why are you looking to grow the company? So I think that's a really important question to ask as founders, as entrepreneurs, I think most of us, if not all of us, have a growth mindset, both in terms of the meaning of that terms psychologically, but also in terms of we want to grow the company, we want to get that next win.

We want to get to that next height and mixer cocktail hour with a lot of other co-founders often asks, like, how big is your company? They're talking about headcount. That's fine. Like headcount is a proxy. And it also informs a lot of the structure of the team. So it's a good first question. But if you're just trying to grow, you create a lot of problems for yourself.

If you're using that headcount as a barometer of your success, you create a lot of problems for yourself. That growth has to be with purpose. It has to be tied to the performance of the business. It has to be tied to what's needed next year in order to succeed. And so when you're thinking about either headcount growth, revenue growth and you're planning out where you're headed, I would advise people in the first instance just ask why?

Why do I need to grow? How do I need to grow, and what's required at the core in order to power that? We're also environment where growth at all costs is are rewarded anymore. Ultimately, you have to get to growth that sustainable and profitable. And so it requires a little bit more diligence and scrutiny than we've had in the past and really questioning, how am I going to grow, why do I need to grow, and what's required in order to hit the next milestone in terms of revenue or company growth?