Most productivity software companies fail because they can't solve one fundamental problem: people are terrible at valuing their time. But what happens when you crack the code on making time itself a shared resource rather than a personal asset?
Matt Martin, CEO of Clockwise, turned this insight into an AI scheduling assistant used by Netflix, Pinterest, Uber, and OpenAI. After raising $45 million in Series C funding, his company has proven that the secret to productivity isn't just better tools—it's treating time as a coordination problem that software can actually solve.
In this deep dive, Martin reveals the counterintuitive lessons from building a product-led growth company: why they didn't monetize for nearly three years, how product-market fit is never truly "found" but constantly rediscovered, and why the biggest growth features must usually stay free.
Watch the full interview now on EO's YouTube channel! Below is the complete transcription of the interview. Minor edits have been made for clarity and readability.
Key Highlights:
"The biggest question we had was, Can this even work? Like, we want to optimize calendars automatically with an algorithmic approach. Is that even plausible?"
"There's kind of like no replacement for doing monitored user sessions. We would ask users to come to our office, we'd come to them and we just sit down and watch them use the product, and it's just like wildly rich with information."
"We wasted a lot of thought cycles on do we have product market fit or not. But looking backward, we had a few key metrics that we were oriented on that were way more impactful to guiding us."
"We probably monetized too late. Any time spent developing features for users who are ultimately not going to pay us, that doesn't either fuel the product growth engine or work on helping to convert free users to paid users, it's kind of wasted time."
"Product market fit is both a factor of staying very in touch with what your customers' expectations and demands are. And those expectations can shift because of outside forces like a market correction, because a competitor makes a competitive product, because an incumbent decides to enter your space."
"There's kind of like no replacement for doing monitored user sessions. We would ask users to come to our office, we'd come to them and we just sit down and watch them use the product, and it's just like wildly rich with information."
"We wasted a lot of thought cycles on do we have product market fit or not. But looking backward, we had a few key metrics that we were oriented on that were way more impactful to guiding us."
"We probably monetized too late. Any time spent developing features for users who are ultimately not going to pay us, that doesn't either fuel the product growth engine or work on helping to convert free users to paid users, it's kind of wasted time."
"Product market fit is both a factor of staying very in touch with what your customers' expectations and demands are. And those expectations can shift because of outside forces like a market correction, because a competitor makes a competitive product, because an incumbent decides to enter your space."
The Coordination Problem That Started Everything
How did you initially discover this problem as something that was worth solving as a business idea?
Matt Martin: I was at a company called RelateIQ and I was a front-end engineer and an engineering manager. That company was acquired by Salesforce, and I was at Salesforce after the acquisition, managing my software team, and just seeing how difficult it was for me to get time to be proactive about work.
It felt like I was constantly in a reactive mode. I was jumping from meeting to meeting, I was jumping from problem to problem, I was helping out in a one-on-one, but I didn't have a lot of time to sit down and actually make forward progress on larger projects. And I was also observing that on my team.
Among software engineers, colleagues on design and marketing, people were having a difficult time getting time in their workday for really important work. In that environment, I was just seeing like, there's a really deep issue here, because these are really intelligent, really motivated people, they want to deliver great work, they want to be able to sit down and help deliver great high impactful product for the company, but their schedules are kind of conspiring against them and getting in the way.
What I think led to the founding of Clockwise is one key insight, which is that really, if you started to pull apart people's schedules, the issue wasn't necessarily that there wasn't any time. The issue is that the time wasn't being spent in the right ways, and if you looked at how it was structured, it was just a coordination problem.
People would go schedule a meeting at the time they could find, which happened to be a really bad time for the four people they were scheduling with, or somebody would send a Slack message right in the middle of when somebody's trying to go heads down working, distracting them. And so, all that work could probably be done effectively, if there was just something that was helping to coordinate, and helping to coordinate across all the teammates.
It felt like I was constantly in a reactive mode. I was jumping from meeting to meeting, I was jumping from problem to problem, I was helping out in a one-on-one, but I didn't have a lot of time to sit down and actually make forward progress on larger projects. And I was also observing that on my team.
Among software engineers, colleagues on design and marketing, people were having a difficult time getting time in their workday for really important work. In that environment, I was just seeing like, there's a really deep issue here, because these are really intelligent, really motivated people, they want to deliver great work, they want to be able to sit down and help deliver great high impactful product for the company, but their schedules are kind of conspiring against them and getting in the way.
What I think led to the founding of Clockwise is one key insight, which is that really, if you started to pull apart people's schedules, the issue wasn't necessarily that there wasn't any time. The issue is that the time wasn't being spent in the right ways, and if you looked at how it was structured, it was just a coordination problem.
People would go schedule a meeting at the time they could find, which happened to be a really bad time for the four people they were scheduling with, or somebody would send a Slack message right in the middle of when somebody's trying to go heads down working, distracting them. And so, all that work could probably be done effectively, if there was just something that was helping to coordinate, and helping to coordinate across all the teammates.
Building in the Kitchen: The Early Product Decisions
How did you prioritize which features to focus on when there are all these different problems that you see?
Matt Martin: There's always more feature requests and more things to build than you have time to do. What can separate out really excellent execution from mediocre execution is focus and making sure that you're spending time in the areas that really matter in terms of moving the business forward.
It's really about prioritizing what's gonna yield the most impact for your business as you try to validate and progress it, and that changes with stage. Take you back all the way to the early founding days of Clockwise when just me and my two co-founders on my kitchen table. The biggest question we had was, Can this even work?
We want to optimize calendars automatically with an algorithmic approach. Is that even plausible? And so that's what we prioritized doing first. What you're making from a business strategy decision standpoint is, what's the biggest risk that I need to de-risk in order to get to the next milestone for the business.
In those very early days, one of the biggest milestones was getting it live in customers' hands. So you take a step back, what do I need to de-risk in order to actually get it in customers' hands? Well, I need to figure out if this actually works at all. I need to go get live calendar data. I need to find a friend who's willing to share their real calendar data. And then we need to run a bunch of experiments on it in memory to see if we can actually get this thing to run.
It's really about prioritizing what's gonna yield the most impact for your business as you try to validate and progress it, and that changes with stage. Take you back all the way to the early founding days of Clockwise when just me and my two co-founders on my kitchen table. The biggest question we had was, Can this even work?
We want to optimize calendars automatically with an algorithmic approach. Is that even plausible? And so that's what we prioritized doing first. What you're making from a business strategy decision standpoint is, what's the biggest risk that I need to de-risk in order to get to the next milestone for the business.
In those very early days, one of the biggest milestones was getting it live in customers' hands. So you take a step back, what do I need to de-risk in order to actually get it in customers' hands? Well, I need to figure out if this actually works at all. I need to go get live calendar data. I need to find a friend who's willing to share their real calendar data. And then we need to run a bunch of experiments on it in memory to see if we can actually get this thing to run.
Do you think you took a different approach than other competitors in terms of making you stand out and be more innovative?
Matt Martin: Because it's a pretty popular space, and it's pretty densely populated with tools, it really benefited us to have an opinion at the start, and to have a little bit of an edge to what we were providing, so that we could entice and find those early adopters that were passionate about it.
If you try to push out a general purpose product that appeals to everyone, you're gonna stretch yourself too thin, you're not gonna find that initial niche that really advocates for you, and you need that. You really need that in the early days.
For us, our strong perspective is that everybody needs deep work. Everybody needs time for deep work, and deep work is meaningfully different and substantively different than just little blocks of 30 minutes or 15 minutes on your calendar. Cal Newport, a professor at Georgetown, wrote a whole book about this, and so we kind of piggyback on some of that messaging to find those people who that really resonates with, and it turned out to be a lot of software engineers.
We found that initial core audience in order to break through the noise a little bit, and then you can start to tailor your outreach and your conversation and your materials towards that initial audience.
If you try to push out a general purpose product that appeals to everyone, you're gonna stretch yourself too thin, you're not gonna find that initial niche that really advocates for you, and you need that. You really need that in the early days.
For us, our strong perspective is that everybody needs deep work. Everybody needs time for deep work, and deep work is meaningfully different and substantively different than just little blocks of 30 minutes or 15 minutes on your calendar. Cal Newport, a professor at Georgetown, wrote a whole book about this, and so we kind of piggyback on some of that messaging to find those people who that really resonates with, and it turned out to be a lot of software engineers.
We found that initial core audience in order to break through the noise a little bit, and then you can start to tailor your outreach and your conversation and your materials towards that initial audience.
The User Feedback Paradox
What do you do at Clockwise to gather feedback from users and incorporate it into product development?
Matt Martin: One of the tricky parts about Clockwise is that the promise of the product is to automatically give you more time in your schedule. And so, one of the things that allows us to break through that noise is not just have an opinion about what the product provides to you, but also that, hey, for a very low investment, you can get pretty high ROI in the background automatically.
Now, I mentioned that because that means customers kind of don't want to talk to you. The whole promise of the product is we're not gonna bug you, and that it's automatic and it's easy to set up. For very complicated products and for products that are high implementation cost, you have an excuse to talk to your user or customer. For us, most people just wanted to use it, set it, forget it.
While certainly there were a lot of patterns where I would email people if I saw a new logo come in that I thought was interesting, I would try to loop them in. Early adopters love to talk about product. They'll love to feel like they have an inside track to what you're building, and they have an influence. So I'd usually use that as an excuse.
We had to look at a lot of automated methods. So we use a variety of tools to actually watch sessions, to look at a lot of the quantitative data to see how things were trending, and to really be able to troubleshoot what users were doing and feel in their shoes.
There's kind of no replacement for doing monitored user sessions. We don't do as many of these anymore, but in the early days when we had lower volume users, we would ask them to come to our office, we'd come to them and we just sit down and watch them use the product, and it's just like wildly rich with information.
Now, I mentioned that because that means customers kind of don't want to talk to you. The whole promise of the product is we're not gonna bug you, and that it's automatic and it's easy to set up. For very complicated products and for products that are high implementation cost, you have an excuse to talk to your user or customer. For us, most people just wanted to use it, set it, forget it.
While certainly there were a lot of patterns where I would email people if I saw a new logo come in that I thought was interesting, I would try to loop them in. Early adopters love to talk about product. They'll love to feel like they have an inside track to what you're building, and they have an influence. So I'd usually use that as an excuse.
We had to look at a lot of automated methods. So we use a variety of tools to actually watch sessions, to look at a lot of the quantitative data to see how things were trending, and to really be able to troubleshoot what users were doing and feel in their shoes.
There's kind of no replacement for doing monitored user sessions. We don't do as many of these anymore, but in the early days when we had lower volume users, we would ask them to come to our office, we'd come to them and we just sit down and watch them use the product, and it's just like wildly rich with information.
Rethinking Product-Market Fit
What were some initial signs that suggested Clockwise was resonating with the target market?
Matt Martin: Product market fit is tricky. It's ill-defined, even though everybody thinks they have a definition. I would say just pick one, pick a metric that you're really oriented on, and pick a metric that you think is a leading indicator for your business. Maybe stop asking the question about product market fit for a second, because I think it's really amorphous, and it can be a kind of a black hole distraction for people.
In the early days, we wasted a lot of thought cycles on do we have product market fit or not. But looking backward, we had a few key metrics that we were oriented on that were way more impactful to guiding us on our journey and getting us to product market fit than this kind of weird question about do we have it?
In the really early days, that was, are people inviting other people? If we get one user in, are they pulling other people in inside their same organization, which we just looked at the domain. So we have a user at Lyft.com. Are other users from Lyft.com joining now or not? That's a sign of something, and it's a leading indicator of something that's really important to our business.
The second one is, are people adopting a critical feature that unlocks a lot of the power of Clockwise, which is called flexible meetings. If you're building a product, what's your most critical feature that's a leading indicator that that user is going to be a successful user of your product? If they use this, the odds of them being a long term successful user go way up.
The final layer, which I think you do need to actually know whether you have product market fit, didn't come till a lot later. For a productivity PLG company, we have user growth, we have adoption of key features, we have engagement, we have retention. Are they going to pay for the thing and are they going to keep paying for the thing?
In the early days, we wasted a lot of thought cycles on do we have product market fit or not. But looking backward, we had a few key metrics that we were oriented on that were way more impactful to guiding us on our journey and getting us to product market fit than this kind of weird question about do we have it?
In the really early days, that was, are people inviting other people? If we get one user in, are they pulling other people in inside their same organization, which we just looked at the domain. So we have a user at Lyft.com. Are other users from Lyft.com joining now or not? That's a sign of something, and it's a leading indicator of something that's really important to our business.
The second one is, are people adopting a critical feature that unlocks a lot of the power of Clockwise, which is called flexible meetings. If you're building a product, what's your most critical feature that's a leading indicator that that user is going to be a successful user of your product? If they use this, the odds of them being a long term successful user go way up.
The final layer, which I think you do need to actually know whether you have product market fit, didn't come till a lot later. For a productivity PLG company, we have user growth, we have adoption of key features, we have engagement, we have retention. Are they going to pay for the thing and are they going to keep paying for the thing?
The PLG Paradox: From Users to Enterprise
Can you tell us about the transition from targeting individual users to expanding to the B2B side?
Matt Martin: For the last probably five years or so, there's a lot of buzz and excitement around product-led growth companies. Canonical examples here are companies like Slack, Dropbox, Atlassian. The advantage of that model is that you can go out and acquire users at scale, and you can use additional users to acquire more users.
The seedy underbelly that nobody tells you about is that it's way easier just to go sell the dang thing. With product led growth, what you're doing is creating a product that's good enough to pull people in the front door, convert them to users, and then ultimately convert them to paying users, and scale that into the business.
All these PLG companies are fundamentally B2B companies. It's just, it starts in a way that looks like it's B2C, because anybody can go to your website and sign up. But really the fundamental engine of their revenue comes from larger organizations buying a lot of licenses.
We have never had a purely B2C version of Clockwise, in that, everybody who signs up actually has to use a calendar address that is associated with a business account. So if you try to go sign up for Clockwise with Hannah at gmail.com, it actually doesn't work. We will reject you at the start.
It hurts our virality, but we really don't, from a revenue perspective, ever make much off of single seat users. So by only taking in users that have some capacity to scale into the larger organization, it helps to filter at the top users that actually can be customers.
The seedy underbelly that nobody tells you about is that it's way easier just to go sell the dang thing. With product led growth, what you're doing is creating a product that's good enough to pull people in the front door, convert them to users, and then ultimately convert them to paying users, and scale that into the business.
All these PLG companies are fundamentally B2B companies. It's just, it starts in a way that looks like it's B2C, because anybody can go to your website and sign up. But really the fundamental engine of their revenue comes from larger organizations buying a lot of licenses.
We have never had a purely B2C version of Clockwise, in that, everybody who signs up actually has to use a calendar address that is associated with a business account. So if you try to go sign up for Clockwise with Hannah at gmail.com, it actually doesn't work. We will reject you at the start.
It hurts our virality, but we really don't, from a revenue perspective, ever make much off of single seat users. So by only taking in users that have some capacity to scale into the larger organization, it helps to filter at the top users that actually can be customers.
Product-Market Fit Is Never Static
How were you able to conclude that product-market fit is not something that's static?
Matt Martin: I can think of several moments in the journey of Clockwise where I'm like, we got it, we got product market fit, and then you go get it again. When we first saw users inside an organization scaling up with that nice hockey stick curve, we're like, holy crap, we've got it. And then we're like, well, we gotta get a lot more of them.
When we started to see it spread across other companies, we're like, oh, we've really got something. And then we had, but none of them were paying, and so we had to put in a monetization model that worked for everybody. Let me tell you, we were scared. We had gotten through that first one, and then we're gonna go ask people to pay, and we're like, is this gonna work? Like, is anybody gonna pay?
Then that started working, and we're like, oh my God, we are off to the races. But then you get to that next hurdle. It's like, OK, we got people to pay, how do we start to scale this out into larger enterprises? And then something like zero interest rates stop being reality. Budgets tighten, the software ecosystem goes through what I think is fair to qualify as a mild recession.
You have to relearn product market fit. All of a sudden, that benchmark by which people are saying, yes, Clockwise is valuable enough for us to pay pretty good money on a sustained basis, that got moved up because all those businesses have tighter budgets and are more strict about what they're spending money on.
The process of finding product market fit is both a factor of staying very in touch with what your customers' expectations and demands are. And those expectations can shift because of outside forces like a correction of the market. They can shift because a competitor makes a product that's competitive to yours. They can shift because an incumbent decides to enter your space.
When we started to see it spread across other companies, we're like, oh, we've really got something. And then we had, but none of them were paying, and so we had to put in a monetization model that worked for everybody. Let me tell you, we were scared. We had gotten through that first one, and then we're gonna go ask people to pay, and we're like, is this gonna work? Like, is anybody gonna pay?
Then that started working, and we're like, oh my God, we are off to the races. But then you get to that next hurdle. It's like, OK, we got people to pay, how do we start to scale this out into larger enterprises? And then something like zero interest rates stop being reality. Budgets tighten, the software ecosystem goes through what I think is fair to qualify as a mild recession.
You have to relearn product market fit. All of a sudden, that benchmark by which people are saying, yes, Clockwise is valuable enough for us to pay pretty good money on a sustained basis, that got moved up because all those businesses have tighter budgets and are more strict about what they're spending money on.
The process of finding product market fit is both a factor of staying very in touch with what your customers' expectations and demands are. And those expectations can shift because of outside forces like a correction of the market. They can shift because a competitor makes a product that's competitive to yours. They can shift because an incumbent decides to enter your space.
The Three-Year Monetization Mistake
You mentioned that you waited almost two years to turn on monetization. Can you elaborate on this lesson that you gained?
Matt Martin: We started this company at the very tail end of 2016. We really got off the ground in 2017. We were building in private beta for a while, it took us a while to figure out the mechanics of the product, get it working, get it to scale, and we didn't release it publicly really until 2018, 2019. Then it started to rip, and we pushed on monetization really for the first time in 2020. So like three years into the company.
I say that we probably waited too long. It works for us, but it creates very weird incentives inside the company, if you don't have monetization as an element of how you build. If you're not asking users to pay, you can actually spend a lot of time building product and building features that only accrue value to users who are never going to pay you anyways.
There's no better filter for users and the ones that really matter and understand your product and ascribe value to it than asking them to pay for it. Those are the users that you need to grow. The other users, I love them to death, but if they're ultimately not going to pay us, they really don't matter that much for the business unless they're going to bring another user in.
Any time spent developing features or product for them, that doesn't either fuel the product growth engine or work on helping to convert that free user to paid user, it's kind of wasted time. Time is a very precious commodity, especially for startups. You are resource constrained always, all the time, and so you have to use those in the most focused way.
I just think you will have cleaner learnings, you will probably waste fewer cycles if you're incorporating that into the product from the start.
I say that we probably waited too long. It works for us, but it creates very weird incentives inside the company, if you don't have monetization as an element of how you build. If you're not asking users to pay, you can actually spend a lot of time building product and building features that only accrue value to users who are never going to pay you anyways.
There's no better filter for users and the ones that really matter and understand your product and ascribe value to it than asking them to pay for it. Those are the users that you need to grow. The other users, I love them to death, but if they're ultimately not going to pay us, they really don't matter that much for the business unless they're going to bring another user in.
Any time spent developing features or product for them, that doesn't either fuel the product growth engine or work on helping to convert that free user to paid user, it's kind of wasted time. Time is a very precious commodity, especially for startups. You are resource constrained always, all the time, and so you have to use those in the most focused way.
I just think you will have cleaner learnings, you will probably waste fewer cycles if you're incorporating that into the product from the start.
The Art of Pricing: Growth Features Must Stay Free
How have you structured the pricing plans for Clockwise, including how you decide which features are free based on their growth potential?
Matt Martin: You can't ever lose the vision. It's easy to start to look at a packaging page, and you can kind of slice and dice things into oblivion, and the product overall has to have a holistic perspective on what it's providing in the world. You have to anchor first and foremost in what is the value that we're providing in the world and what is our vision for this product.
In an ideal world, the massive drivers of value are behind the paywall, and the massive drivers of user acquisition are not behind the paywall. That's unfortunately not always the case. Slack's a good example. The deep value of Slack is becoming the de facto place where people message and converse, and where they have a rich history of information and a lot of integrations and tools that they use.
But you're not going to become the deep consistent record of truth until you have some scale of adoption inside the organization, and the way that you go and acquire other users to adopt them is you chat with them. So things like Slack Connect absolutely should be free. You should be incentivized to connect with more people, bring them onto the product, and to start chatting with them.
It's really nice if you have that deep driver of value that's very clear that you can charge for, and you have the drivers of virality and adoption that are free. It's rarely that clean, so you have to look across your feature set. It always ends up devolving into a gut call. You look at the user data, you look at what people are using, you inform yourself as much as you can, and then you just make a call.
What I'm looking at when we're pricing and packaging is, what is the most important value driver for Clockwise for this feature. If the most important driver of value is that this is something that spreads us out to the world, and we're in a growth mode, then I will invest in putting that in the free plan. I'm foregoing some revenue, but I'm gonna put an investment in the business by essentially making that marketing dollars.
In an ideal world, the massive drivers of value are behind the paywall, and the massive drivers of user acquisition are not behind the paywall. That's unfortunately not always the case. Slack's a good example. The deep value of Slack is becoming the de facto place where people message and converse, and where they have a rich history of information and a lot of integrations and tools that they use.
But you're not going to become the deep consistent record of truth until you have some scale of adoption inside the organization, and the way that you go and acquire other users to adopt them is you chat with them. So things like Slack Connect absolutely should be free. You should be incentivized to connect with more people, bring them onto the product, and to start chatting with them.
It's really nice if you have that deep driver of value that's very clear that you can charge for, and you have the drivers of virality and adoption that are free. It's rarely that clean, so you have to look across your feature set. It always ends up devolving into a gut call. You look at the user data, you look at what people are using, you inform yourself as much as you can, and then you just make a call.
What I'm looking at when we're pricing and packaging is, what is the most important value driver for Clockwise for this feature. If the most important driver of value is that this is something that spreads us out to the world, and we're in a growth mode, then I will invest in putting that in the free plan. I'm foregoing some revenue, but I'm gonna put an investment in the business by essentially making that marketing dollars.
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