This is How Top Engineers Manage Their TimeㅣClockwise Matt Martin (1/2)

In this interview, we sit down with Matt Martin, the founder of Clockwise, the revolutionary AI scheduling and calendar automation tool. With Clockwise, organizing your time becomes effortless, whether you're managing your own schedule or coordinating with your entire team. Discover how Clockwise has transformed the way over 40,000 organizations operate, enabling them to prioritize what truly matters.

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.

There are a lot of things that I'm proud of about what we've accomplished at Clockwise, but I think the biggest achievement is creating an engine, a scheduling engine that can take in information about how you work, your preferences, what's happening in your day, what's happening in your organization, and automatically move meetings to create a better schedule. That's something when we first introduced that idea to the world and we were pitching investors, a lot of people laughed us out of the room because it sounds crazy, and it is a little bit crazy, but being able to do that reliably, effectively, in a way that empowers our users is probably our crowning achievement. And we moved 17 million plus meetings so far in Clockwise history.

So I'm a time nerd and I love productivity software. I love calendar audits. I was working with my engineering team, and I was questioning why the number one complaint I get is that they don't have enough time to go heads down, because you go look at their calendar and it's like, well, relative to my calendar, it looks pretty good. You've got to unpack that problem a little bit more, because if you just look at what's going on at the surface level, you're not getting the whole picture.

And after pulling that thread for a while, what we came to is the conclusion that time inside of these organizations becomes so networked. It's not just the calendar system where literally somebody can reach out and grab time for me by just looking at my calendar, but also people are sending emails or sending Slacks. They're sending Jira tickets, they're sending messages on Confluence. We're asking each other for time and attention all throughout the day.

This gets a little bit philosophical, but I think it's a really important piece to understand what we do with Clockwise, which is: if you have a really valuable resource, and nothing's more valuable than time (both philosophically but also as a brass-tacks matter, payroll is the number one expense inside of most knowledge worker organizations), you have this really, really valuable resource. It's become a shared resource, but nobody's regulating it, and that creates a classic tragedy of the commons. This goes to an economic principle where you have a shared resource, and it gets eviscerated because nobody's actually regulating it. The classic example is everybody can spot pollution in the air; unless you have a regulator to actually mandate for the public benefit, you can end up with a bad result.

But time is similar to that, where everybody's thinking about how they need to get their stuff done and just grabbing from others. So you need to have something that comes in and helps actually coordinate amongst everyone, for the good of the whole team, for the whole organization. At the core, that's our philosophy at Clockwise: we want to help that individual get the best schedule by looking out for them across the team, across the people they meet with, across the organization. And we also think that unless you do that, you're going to end up in a bad outcome.

One thing that I would advise everybody to do, if you just take away one tip: it's not easy, it might feel like a luxury, but just spend a little bit of time at the start of your week asking, what are the most critical things for me to accomplish this week? And that list should only be three items, maybe five. Then look at whether you have the time to do it. And when I say look at the time, let's say I need to knock out this presentation and I need to spend some time talking to customers, well, then look at your calendar and see when that's going to happen. Just in broad buckets. You don't need to schedule out the exact time, just check whether you have the heads-down time to accomplish that. And if you don't, move things around and make sure you do, and block it off.

Some people love time blocking. They love to take that specific item and say, I'm going to do this presentation Wednesday afternoon. If you want to do that and it works for you, awesome, I say go for it. But for me, it's hard to plan out exactly what I'm going to do and when. So I take those broad priorities and I just make blocks of focused time that say, hey, if I have these blocks and I have my task list, I'll at least have enough time in the week to get my most important priorities done.

The idea of helping people get a better schedule, getting a better, more productive work environment, really spoke to me as a manager. It spoke to me as an engineer, but it also spoke to me just as a human who's been focused on productivity software my whole life. And it's one of those rare ideas, I think they're very rare, where the value for the end user and the value for the buyer align directly, in a way that creates a high degree of focus and clarity for what sort of product you have to deliver.

And for us, if we deliver a great product that really gives you a better schedule, that's going to help that team work better, that's going to help that company work better together. It's going to help them ship faster. It's going to help them deliver more for their customers. The value for that end user, the team, and the company are all aligned. So we can focus on just delivering something that really helps that user.

And in the process: I think there are companies out there that are charitable organizations, that are really driving big humanity-level changes, and I'm not going to sit here and pretend that Clockwise is a capitalistic endeavor. However, and this is really important to me, because of that value alignment between the individual, team, and company, we can still drive huge human-level impact. If you get a good day where you get to jam and do what you want to do, you go home happier, you live your life happier. And that gives me energy on a day-to-day basis.

Seven years after founding, we're in this early development phase where, again, we had the clarity of where we want to take this thing, but we just weren't sure how the initial product would manifest. So one of the first things we did is reach out to friends and family to figure out some places that we could test this out, and early on, we got connected with a high-up engineer.

I remember going in, and we had gotten a meeting with either a director or a VP level in the engineering organization, and they allowed us to connect Clockwise in a very secure, closed way to their corporate calendar. What we did is we used that in order to power a demonstration of what the optimization can yield. That was the initial question: if Clockwise is in our power system and we allow it to move our meetings, is there actually a benefit there? Because that was an unknown, people were convinced, but they hadn't seen it before.

So we connected to this power system. We had hundreds of people, and we ran it virtualized, we didn't do this in Google Calendar, but we took all the real data and ran an optimization of their whole calendar system in a way that we could show it to that leader. We ran it, and you could see all the meetings moving around. You could see what would impact people's schedules. You could inspect all of it.

And the result came back: we were giving them back thousands of hours, thousands of hours over the course of a couple of months. We were actually driving so much productivity for that organization. His eyes just lit up, and he said, yeah, if you can deliver that, I will buy it.

We raised our seed round from Accel Partners in 2017, and we were focused at that point on trying to unlock this initial version of the product that would deliver value and allow us to expand. When we raised our A round from Greylock Partners, we weren't quite there yet. We had some initial traction, and the results looked incredibly promising in terms of what we could drive, but it just wasn't there yet, so we hadn't released it publicly. We were still in very private beta, and then in the summer of 2019, for the very first time, we opened that up to all Google Calendar users.

At first, we had a bit of a waitlist experience where you had to get through, but more or less we unbound it, we allowed people to access it. And that's where you saw the effort that we put in, in terms of building that viral growth inside the company, start to spin out. We released the product. We saw those initial 1,200 or so users.

We got that initial traction, and it felt great, they were like, is that it? Is that going to work? But then week after week, it just started to spin up, and up, and up. And the important thing is that the growth was compounding: some of those initial 1,200 users seeded interest in their organization, others talked about it on social media, and it just started to spin. It's hard to express in words how exciting that was.

Clockwise is a product that focuses on driving value for the individual, and we had kind of a chicken-and-egg problem in the early days: the product gets way better when you use it with others. It's fundamentally about intersecting with other teammates' calendars and being able to optimize the whole. If you just have one person, we can deliver some value, but it's not as remarkable as if you use it with your team. So we had to figure out a way to pull that individual in and get them spun up such that it starts to spread to their team. That was the initial barrier: how do we get the product to start to spread inside of organizations?

It required us to do a few different things. We had to build that single-player value, frankly, a lot of these were bells and whistles around the real meat and potatoes, which is that team-based value of being able to optimize schedules. But we saw that user come in, and of course they want to see what you can do for them today. So we built out things like personal calendar sync, automatically color-coding your meetings, adding travel time, blocking off lunch. These features let people get that instant hit of value while we still drove them toward opting into the meetings they wanted Clockwise to automate.

We tinkered with this for some time, but ultimately found a calibration that allowed that user to come in, use the features, and gave us time to spread inside that organization. That was one of the biggest early unlocks of the company, that early unlock of viral growth inside the organization. That's always been a key driver of our growth.

So we tend to land inside of an organization. Sometimes we land in by people, companies. We land in a company that might be 500, 1,000, 10,000 people, and Clockwise starts to grow inside that company. That's allowed us to mature into places like Uber, Netflix, Pinterest, and Instacart, where we have large deploys that are powering a huge component of their organization. That continues to be a huge driver for us today.

So our mission is to help the world make time for what matters. It's been our mission since day one. We see that often the obstacle for people to get what they want done in the day or in the week is their work calendar; it's those meetings that get in their way. And our vision is to help give everyone a schedule they love.

We want you to feel that. We want you to feel that in your schedule, hopefully on a daily basis, at least a weekly basis. Clockwise helps organizations and teams get more productivity in the week: more time to ship, more time to deliver, more time with customers, more time with clients. That is ultimately what we're driving. But we always try to stay anchored to that vision: if we give you a schedule that you love, all the rest falls into place.