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🌐 How Deel Does Global Compensation. An interview with Jessica Pillow, Global Head of Total Rewards at Deel.
🔐 Bootstrapped Exit, Compliance Tech & Raising From Accel. An interview with Girish Redekar, Co-Founder and CEO of Sprinto.
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HOUSEKEEPING 📨

I’ve been on a serious health and wellness kick lately. I have always been generally fit, healthy and active, and recently started training hard again as a weightlifter, but I am now back doing cardio 5 days a week and even bought myself a sauna which literally sits behind my desk in my office (see me watching my mate Charlie’s YouTube from Sweat City, USA). It’s been great, actually, and I seem to have also unlocked a cardio cheat code.

The image you see above is from a workout today, where I spent ~80% of the workout in zone 2 or higher. For those unfamiliar, this is a great place for heart health and overall wellness. The workout: ball throws. I literally pick up a 15kg ball and I throw it down the length of the gym and back for 30 minutes. It’s insanely easy on the body, and I just potter along listening to a podcast or audiobook while I do it. The up and down motion of picking the ball up works your heart like crazy. If I were to do sled pulls for 30 minutes like this, I would sit between zones 1 and 2 the entire time. If you are looking for a great workout to add to your busy days, give something like this a try. It works wonders. Anyway, here is today’s piece!

INTERVIEW 🎙️

Matt Martin, Co-Founder & CEO at Clockwise

Matt Martin is the Co-Founder and CEO of Clockwise, an AI-powered time management platform that helps organizations optimize their schedules, which he founded in September 2016 alongside fellow RelateIQ alumni Gary Lerhaupt and Mike Grinolds. He holds a B.A. from Dartmouth College (2006) and a J.D. from the University of Pennsylvania Law School (2010), and previously worked as a civil litigator at an Am Law 100 firm in Minneapolis before transitioning into technology.

Before founding Clockwise, Matt gained valuable tech experience as an Engineering Manager and Software Engineer at RelateIQ (acquired by Salesforce for $390 million in 2016) and as VP of Product at LegalReach. Under his leadership, Clockwise has grown to serve over 40,000 organizations including Netflix, Twitter, Atlassian, and Asana, raising $76 million from top-tier investors like Greylock, Accel, and Bain Capital Ventures, including a successful $18 million Series B during the pandemic.

Tell us about the problem you're trying to solve? Why this?

It's a big question actually. I'm a software engineer by background, and the last company I was at got acquired by Salesforce. We had problems with time management even before being acquired, but all of a sudden we went from being a 70-person team down in Palo Alto to being part of this huge organization—I don't know how many people are there now, but at the time it was about 30,000 people.

The difficulty of me and my team finding time to actually do our most impactful work struck me as astoundingly wasteful. The pithy version of what we're trying to solve is the battle that every knowledge worker engages in actually getting time to do their work. You get put in a corporate environment of any complexity, you're pinged on Slack all the time, you're interrupted by meetings, things that people schedule with you. And it just strikes me—you're in the talent space—we spend so much time and energy hiring, recruiting, and training amazing people. Then they get in the company and you go, ‘Okay, now you manage your time and anybody can schedule with you.’ Another PM, a colleague, a boss—it doesn't matter. Your day gets chunked up and it becomes difficult to do impactful work.

We're trying to get people breathing room so they can actually do the work they're hired to do, have more impactful days, and then go home and have their time with their family.

Do you have any quantifiable metrics around engagement and/or wellness?

The wellness side of it is interesting and difficult to quantify. Clockwise is a product where ultimately we sell into businesses, but because we come in via the individual, the individual user's satisfaction with the product is really essential to us since we're coming in bottom-up. So we do look at user satisfaction quite a bit, and we look at engagement and retention as proxies for that satisfaction. But the actual happiness lift, I wish I could give you a stat around that, but it's tough to quantify.

One of the things that's been difficult for us is that prior to the zero-interest-rate bubble popping and the money spigot turning off, the competition for employees was really intense. A lot of companies were in a battle to create a better employee experience. We would get purchased by companies for two reasons: one is that we make the employee base more productive in a measurable way—it delivers impact—but also simply because employees just liked us. We can balance their schedule with their personal life, we can make sure they have time for lunch, etc.

The thing that's become a little bit more difficult is that while competition for top talent is still fierce, the broader labor market has cooled a little bit. It has become more employer-friendly, and employers no longer place as much emphasis on employee experience.

What was the most difficult thing when going from zero to one?

There are so many things that are really difficult. If I had to say one thing, it would be distribution. That's a very common answer for startup founders. I think distribution is difficult for everyone for different reasons. Ours was difficult for a very particular reason, which is that we help optimize schedules and help optimize time so that you can do more impactful work and get a schedule that works better for you. But we're not a calendar.

The startup world and the software world is littered with the tombstones of calendar companies.

So for us, it was this unique challenge of how do we get distribution in a low-friction, high-velocity way while not trying to compete directly against calendar systems themselves. That was tricky from a positioning standpoint, tricky from a technology standpoint, but it was also tricky just from a product standpoint because ultimately, our first product that gained traction was a Chrome extension so you can layer it side-by-side with the calendar. But all of that was very tricky and involved a lot of different hacks along the way and a lot of failure.

What were your first go-to-market bets that bombed? Where did you first see traction?

Clockwise is a company where we've never had a really big pivot in the lifetime of the company. The through line on the idea and the vision has remained the same. Our vision is to give every knowledge worker a schedule they love, and that really has stayed consistent from day one. What's evolved a lot is how the hell do we do that?

The very first version did look like a calendar. That really never came out of internal alpha because we didn't want to be confused with a calendar or compete with existing calendar systems—high bar of entry, also a long tail of features that we don't want to build.

Then we went into early beta testing with a product called Meeting Defender. What it would do is look at your meetings, then help you decide which meetings are really critical that you want to make sure happen with everybody available. But it was really tedious. You had to go through a lot of onboarding that was not frictionless. Another difficult thing about our product is that there's a time delay to value. Every product wants to try to get the delay to value as tight as possible—you want to give them that shot of joy in that first session. For us, you have to set it up and get the value over time.

We eventually landed on a Chrome extension. I dragged my heels on it because Chrome extensions put you in a box and put you in a corner. You're seen as an extension instead of a full-blown application. It turned out to be the best way to deliver it, and that allowed us to augment the existing calendar. Then we had to tinker with a bunch of different methods to get usage actually up so that we got that right to deliver value over time, which is very tricky.

If challenge number one was distribution, challenge number two is how do you get embedded into a user's week so that you get the right to show them value over time? Clockwise, at its core, helps move meetings to create more space in your schedule. We're not going to move all your meetings out from under you on day one—we're going to watch, observe, and make them better over time.

Tell me about raising money in this space?

When you're raising money, ultimately, the story that you're telling is a hero's journey. It's like, ‘Here's the world today. Here's our observation about how it could be different. And here's how we're going to make it way better. And here's what it looks like when it's way better.’ If you're in the VC world—and not every company needs VC funding, I think people make that mistake—but if you're going for scale, if it looks like it could be a huge impact, then ultimately you want capital in order to scale up.

For us, the advantage we had was always that this could be a very large market because ultimately our market is every knowledge worker on the face of the planet. We're not going to capture all the value we deliver in terms of time savings, but a fully loaded software engineer in the Valley is going to cost you anywhere from $200k on the very low end to $500k. And if you're at Meta, I guess a billion these days. But the hourly rate on that is a lot.

The value proposition is always that VCs could look at our story and go, ‘Hey, probably a long shot on success, but if they can hit that mark where they complete that hero's journey, this is a transformative product for a market that is enormous.’ And so you can capture a lot of value. I think that's a lot of what got us into conversations. We had a unique angle on it; we're not another calendar company. We're exclusively focused on the business market. Huge TAM.

At every fundraise, my job becomes telling the story of the progress we've made towards that outcome and towards that hero's journey. And what is it that we have significantly de-risked that makes this outcome more likely. We raised a lot of money before we even had a dime of revenue. We were focused on distribution. We didn't turn on our paywalls until after the Series B. So we raised a seed, A, and B with zero dollars of revenue. The B was a tough one. We were not as far along as I had hoped we would be at that point. We got it done, but I was worried about that round for sure.

How many users did you have at Series B?

At the B, we might have cracked a hundred thousand, but we're not talking consumer scale. Those are 100,000 business seats. There's not a single consumer user in that bucket; that's not part of the way our product works. So they're a little bit more valuable, but the B was tough. It was all raised on good terms, we got incredible investors, but the B really was a tough one. We were not as far along as I had hoped we would be at that point. We got it done, but I was worried about that round for sure.

Is there an analogy for how you position yourself when raising money? Is it similar to Canva?

Yeah, it is. It's like a Canva variant because they have a little bit more of a consumer long tail—anybody can come in and use Canva. We're pretty similar to Slack or Figma. Very product-led growth—people come in, they use it, they bring it into an organization, it spreads. Both by virtue of the fact that it works on calendar systems and given how we built it, it is very viral once it gets inside of organizations. So it tends to land and spread. But yeah, similar to Slack, Figma, etc.

Tell me about your day-to-day job as CEO. What does it entail?

It is so weird. I'm going to take a step back before I take a step forward to answer your question. I probably have undiagnosed ADD. I like different challenges, and I like things getting thrown at me. I don't go around saying that I have a life motto, but to the extent that I do, it's: ‘Throw me in the deep end.’ I like figuring things out as I go and trying to cobble them together. I also really love software engineering, which is on the different end of the spectrum. I get a lot of joy from going in the zone and just building things, but I haven't been able to do that for years because we scaled up the company and other people, and again fortunately for us, we have other people that do software engineering.

Getting back to your question, the reason I start there is that my days are just very different all the time. As somebody who works in a time management space, what I've tried to do is push structure onto what is a very reactive job. I think that any founder CEO is going to be really shitty at their job if they live at either end of the spectrum in terms of being purely reactive or purely proactive. You've got to find a balance for that because my job is pointing the ship in the right direction and making sure everybody's rowing consistently in a line fashion. That does take planning and thinking ahead. But a lot of what you're dealing with once you've set the ship in the right direction is reacting and unblocking people and making sure things are moving, and when there's a tough decision that arises, somebody's making a call on it.

So I try to impart structure on this. For example, Thursdays are basically devoted to my leadership team. I'll have one-on-ones with the leadership team in the morning, we'll have a staff meeting in the afternoon.

Outside of that, customer calls—I still love to do customer research calls to connect directly with people to build my intuition—product strategy sessions where and when I'm needed, I'm still heavily involved in that. Investor relationships don't take up a lot of time, but board management, keeping people apprised of what's happening in the company, legal affairs, HR, the rest of it is kind of reactive, unless we're in a planning cycle.

What does your team look like? Who reports to you?

Right now, in this very moment, I have a Chief of Staff, a CTO, VP of Marketing, VP of Sales and CS, and VP of Design and Product. Those are the folks that are on my direct leadership team. And it's pretty straightforward from there.

What role does the Chief of Staff play?

I could write a whole book on this, because there have been many. It's one of those roles where it's such a broad term. I've met chiefs of staff who are great, but they really are admins—they're chief of staff in name, but they're operating as an executive assistant. And then I've met chiefs of staff who I would kill to have running my whole company. It's very broad.

What is your North Star metric today and why?

This is actually a split-brain response right now. We are on a sprint right now to deliver what we think is going to be a critical piece of AI infrastructure for any assistant platform. So we've more or less paused day-to-day work on core product in order to sprint after delivery of a first—the starting point being an MCP server that can plug into things like Claude, ChatGPT, and other systems to allow those assistants to reach out to Clockwise to connect. I am incredibly pumped about the work we're doing right now. It is so fucking cool. But that means that the North Star metric right now is really hyper-focused on that beta customer set that's testing that out. How many successful loops are we delivering to them?

In core product land—and this is still really important to us, but we're focused on delivering this MCP—we call it ‘high quality active users.’ At its core, it's a user count metric, but it is high quality because we have found over the years that the more we drive really deep usage, it has a very wide net in the organization. If you look at all the users in a given organization where we're at Clockwise, there are probably like 5 to 10% of them that are really deep users. And then the rest are either medium or casual users. They still get value from Clockwise and we charge seats for them and we're happy with them. But it's those really deep users that drive a lot of the adoption and usage. So that's where we focus our energy: making sure that those users are leading the vanguard and that we're developing around them.

How do you set goals? What frameworks and cadence do you use?

I think this is kind of a fascinating one. Your audience might like this because by virtue of the fact that we're on this kind of heads-down, really focused sprint right now to deliver a key technology, we've moved into really quick goal cycles.

So weekly, there's a goal that has to be set in a way that we can say whether you hit or miss it at the end of the week. And then every individual has a weekly goal that they record, which is set against that project-level goal. It sounds like a lot, but it's very quick. It's very light. It's all in one place. It's not in Jira, it's not in Linear. It's just in a spreadsheet and it's just wash, rinse, repeat.

We spend time on Monday where each of the teams will have an extended standup where nobody leaves until everybody understands exactly what they're doing that week and what they're contributing to the larger goal. The reason that I say that I think this is really effective when you have clarity about deliverables is that this is not longer-term, strategic work with high error bars or ambiguity. We're going to ship this and we're going to ship it in this period, give or take maybe a little bit of ambition or slippage. So we know where we're going and now it's just about the drumbeat of making sure everybody knows what they're doing to contribute every single week.

How is your organization thinking about AI operationally and internally?

We're a highly engineering-driven organization, both by focus and also by headcount. So it probably comes as no surprise that we are heavy users of coding tools. The ones that we use right now with a fair amount of intensity; we all use Cursor. Claude Code is taking off quite a bit internally as it is everywhere. So Cursor and Claude Code are probably number one and number two. We also have Graphite in the stack for a variety of uses, but we use some of their AI tooling around PRs and pull requests. Those are the big ones.

In addition to the fact that everybody has a ChatGPT, and actually both a ChatGPT and Claude license right now by virtue of how we're pressing on MCP server stuff, we want to be able to dogfood all of it. So marketing, as you might imagine, is using ChatGPT and the like quite a bit for copy creation and initial drafts and stuff. So we're pretty focused there.

In addition to that, I've made it very clear to everyone that the L&D stipend is available. I think it's pretty clear to everybody, at least in our startup world, that the more AI-based skill sets they have, the better it's going to be for their career. There's innate curiosity on this team by virtue of the people that we hire, but I think it's also pretty clear—I try to be clear about this as well—if you are learning about these tools, learning how to use them, it's going to be better for your career.

One of the ways that I try to put my money where my mouth is is if anybody comes forward where they want to take a class or they want to use a portion of their L&D stipend for something, or they want to go after it, or they want a Claude Code license—no hesitation. I want to enable that to make sure that people have that available. So we have a couple people taking a course on evals right now and how to best do that. I think that there's good alignment if your employees see it as empowering and enabling instead of something that they have to trudge through. If somebody came to me as a software engineer and didn't have literacy in how to use tools like Claude Code and Cursor, it would honestly be a nonstarter for me at this point.

It’s funny because although I'm a techno-optimist—I love technology—I'm not a hype cycle guy. I was not big on crypto, probably due to my lawyer background; I'm a little bit innately skeptical. So it surprises me a little bit that I am so full-bore on people needing to learn these tools, but I think that the value and impact is there. You literally can do more. And so I just can't have skeptics.

How do you get the best out of yourself personally and professionally?

That's a really good question. There are some trite, canned answers that really are true, but everybody says them because they're so valuable. I always make space in my day for a workout. I try to get outside. I try to take a walk to be able to clear my head. I try to make sure that I can spend time with my family. The more interesting, longer answer is that it's been a journey. I've been doing this for eight years now. I think that early on in my founding journey, I got connected with a founder in a bit of a mentor context because he'd been through it a few times. He said something that I appreciated at the time, but not nearly as much as I appreciate it now, having been through the wringer.

He was saying, "Look, you're at the start of your journey and you're sailing an ocean and it's going to be full of waves. And the distance you travel is going to be way longer the bigger those waves are. So if you can control the waves, the ups and downs, your journey's going to be easier, because you're going to be wasting less time going up and down." What he meant is the psychological waves, controlling your own mental cycles and getting a bearing on them.

It never goes away. I think that if you're in this world, you're probably competitive. You probably have a screw loose and you take the losses hard and you take the wins with a lot. But what I've gotten good at or better at, at least, is observing the waves instead of riding them. I can see them. I can see the up and down and I'm a little bit better about not being so fucking in them.

And that’s it! You can follow and connect with Matt over on LinkedIn and Twitter, and don’t forget to check out Clokwise’s website.

HIRING ZONE 👀 

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