In this insightful interview, we had the pleasure of speaking with Szokratesz Kosztopulosz, Events and Operations Manager at Toggl Track, a fully remote company known for its innovative time-tracking solutions. Szoszo, as he’s affectionately called, has been instrumental in organizing Toggl’s company-wide retreats and meetups, ensuring team cohesion and productivity in a distributed workforce. Over the course of our conversation, Szoszo shared his thoughts on the challenges and rewards of managing a globally dispersed team, the importance of building meaningful relationships through in-person meetups, and how these gatherings have become a core part of Toggl’s company culture.

From his experiences with retreats to the role of leadership in embracing remote work, Szoszo offers a wealth of knowledge on building team unity, especially in a remote-first environment. Whether you’re a company leader considering a shift to hybrid or remote models or simply curious about how remote teams thrive, this interview provides valuable insights into the strategies Toggl employs to maintain strong team dynamics across continents.

Can you tell us a little bit about your role at Toggl? How did you start working there, and was it your first experience with remote work? How do you feel about it now?

I joined Toggl six and a half years ago. At that point, Toggl was already a fully remote company. Interestingly, I had a friend, Dajana, who worked at Toggl before me. We actually applied for jobs at the same time, but she got the role, and I didn’t. A year later, the workload became overwhelming for her, and they reached out to see if I was still interested. I was, and that’s how I started my journey here.

This is my first experience working remotely full-time, and I haven’t worked for other companies that are even partially remote. Before Toggl, I did have the occasional work-from-home day, but it was rare, and I had to beg my manager for it. At that time, it felt like I had to fight to work from home just to get things done.

When I first started working remotely at Toggl, it took some time to adjust. The culture was still transitioning. For example, back then, we used to greet each other on Slack every morning at around 9 or 10 a.m., just like you would say good morning in a physical office. In the afternoons, we’d say goodbye or let the team know when we were heading out for lunch, as if we were all in the same space.

Over time, the culture shifted. We stopped doing that because we realized it was unnecessary for a remote environment. It felt like a subtle pressure to align everyone's schedules, almost as if we were pretending to be in a physical office, but distributed. Nowadays, some teams might still do it, but overall, we’ve moved towards encouraging people to work on their own schedules.

Toggl is not just remote-first; we are a fully remote company. Everyone is trusted with their own time management, and we give people the freedom to create a work-life balance that works for them. Of course, there are meetings to attend, but overall, our team members are accountable for managing their own time and responsibilities. This trust and flexibility are key to fostering a healthy remote work culture.

Does that mean you’ve also changed the way you work? It sounds like you moved from being more work-oriented—where everyone has to work at the same time—to being more project-oriented, where you focus on inputs rather than when the work gets done. Of course, there are situations where some things can’t wait, but in general, has this shift occurred?

Yes and no.

As a remote company, we’ve always had people working from different time zones—Europe, the Americas, East Asia—so we never really had complete time overlap. It was never about everyone working at the exact same time. For example, I’m not a morning person, so starting work at 10 a.m. was never an issue as long as it resembled a workday.

We’ve always been more interested in the results than in the number of hours worked. It’s funny because our main product, Toggl Track, is a time-tracking solution. But it’s never been about how many hours you worked—it’s about understanding how much time a certain project takes and analyzing what consumes more or less time. The exact hours don’t matter; it’s just data that helps us improve.

In fact, we have a very strong anti-surveillance ethos. Our support team often shares funny stories with me about this. For instance, some companies ask us if we could add a feature in Toggl to take screenshots of their employees’ screens to make sure they’re working. Our support team is polite, but they basically tell them, "That’s not the way to do business. If you don’t trust your people, no tool on earth will fix that."

We’ve transitioned from informal practices to an official policy called RAFT—Results and Accountability First at Toggl. We even have a well-structured FAQ for employees, which is a public document, to make everything clear. It’s a pretty solid system.

Does this mean that having good documentation is essential for a successful remote working environment?

If everything is accessible to everyone and new hires are properly onboarded within the first few days or weeks, it makes all the difference. We’re always improving our onboarding process, but we make it very clear from the beginning that we care about results. However, this is a double-edged sword. If we say we’re only interested in results, and then someone ends up working 14 hours a day, seven days a week, we’ve missed the point.

We’re not just about results—we’re about getting results while staying true to our culture, which means you shouldn’t be working 14-hour days. You mentioned earlier that sometimes projects need immediate attention. Well, at Toggl, our rule on Slack is that you have 24 hours to respond.

We’re big on asynchronous communication and working at your own pace. There's hardly ever an emergency so urgent that it requires immediate attention. If something can wait for 24 hours, it should.

My role can be different, sometimes requiring a quick reaction. But we’ve even adjusted that, because constantly reacting to things just creates more tension. The essence of working remotely at Toggl is simple: do your job, collaborate with others, bring results. No one cares if it's done at 10 a.m., 10 p.m., on a weekend, or from a beach.

We even have a Slack channel called My Office Today where people share pictures of their workspaces, whether it's from a nice location or just wherever they are. Why would you hide that you're working from the beach if you're delivering results? It makes no sense.

Thankfully, our board and CEO are very supportive of this approach. Our CEO, Alari Aho, who is also the founder, is deeply invested in the idea of deep work—uninterrupted, smarter work. We used to have a T-shirt that said exactly that: “Work smarter, not harder.”

Our whole philosophy revolves around getting results without worrying about traditional logistics. But there's an important balance here—we don’t want anyone to burn out. It’s not about squeezing every last drop of productivity. It’s about results while maintaining a healthy work-life balance. If someone can't achieve results within normal working hours, we need to rethink the workload or hire additional help.

It’s all about trust and accountability in a remote culture. You can work when and where you want, but you still have to deliver. You can’t just sit on a beach for weeks and do nothing—it’s about trusting employees while also holding them accountable for their work.

Many reports mention that results are closely tied to team cohesion. Considering that your teams work across different time zones and regions, how do you ensure team cohesion? Have you noticed this as a challenge, and how do you address it?

We tackle this challenge through meetups or retreats—whatever term you prefer. As I mentioned, we have colleagues spread across the globe: Europe, East Asia, New Zealand, Australia, South America, North America, and some in Africa. So, we’re very distributed when it comes to time zones.

For some roles, like our support agents, being distributed is actually beneficial because it allows us to offer near 24-hour support to our customers. We might have a small gap in coverage, but it’s pretty close.

For other teams, it makes more sense to hire within specific time zones—like Europe—so there’s enough overlap during the working day to coordinate and discuss things in real-time.

But the real secret to ensuring team cohesion is meetups and retreats. Bringing everyone together for a week helps foster and nurture relationships. When they return home and get back to work, those personal connections make remote collaboration smoother and more effective.

Many companies organize retreats retroactively, once they start noticing issues within teams. However, Toggl has integrated meetups into its strategy, making them regular events. Can you share your thoughts on this approach, and how often do you find meetups to be most effective?

We've experimented with different setups over the years. When I joined Toggl, things were much different. Originally, Toggl was a traditional Estonian company with an office where about 15 to 20 employees worked from 9 to 5. But as the company began hiring internationally, it became obvious that Estonia’s talent pool was too limited, and we shifted to hiring remotely.

Initially, there was a need for everyone to meet face-to-face, so we organized one company-wide meetup each year. Fast forward to 2015-2016, Toggl became fully remote, and meetups became a crucial part of the company’s culture. In the early days, we had two full-company meetups and two team meetups each year. Over time, that evolved. We started having department meetups, team meetups, and eventually settled into a structure of two company-wide meetups and one team or department meetup.

What makes our approach unique is that we don’t plan meetups just to solve a problem. Meetups are a core part of our culture. The primary goal of a meetup is to meet and build relationships—everything else comes afterward. Once the logistics of a meetup are in place, we decide on the specific goals or projects for that particular gathering.

Team leads have the freedom to decide whether to focus on a special project, discuss topics that fell through the cracks, or simply bond. Some meetups are more work-focused, especially larger ones where we have Q&A sessions with management or discuss cross-departmental initiatives. But smaller team meetups can be more laid-back, like our support team spending a week in Croatia doing their regular work while enjoying time together.

At Toggl, we firmly believe that relationships are built in person and maintained online. You can’t create strong bonds just through virtual meetings. Our retreats are designed to foster those bonds. For example, we used to have something called the Toggl Challenge, where we’d divide the company into teams and do something completely unrelated to work, like a hackathon. It was a great way to unwind and build camaraderie.

While our setup has changed over the years, the core philosophy remains the same: trust, collaboration, and fostering meaningful relationships. We’ve found that after meetups, productivity tends to skyrocket. People return feeling more connected and energized, and that reflects in their work.

After a meetup, do you measure certain things to evaluate how it went? What metrics do you look at in follow-ups or analyses? What are the key things you focus on improving, and how do you measure those?

Szoszo: That’s an interesting question. When I first started, I was given KPIs and tasked with measuring logistics and overall satisfaction, but to be honest, it's not rocket science. It’s just about ensuring everything runs smoothly, and while that takes skill, it's more about knowing the people and getting things done well.

For example, when our meetup satisfaction reached 93%, we had discussions like, “Should we aim to raise it to 95%? What does that even mean in practice?” We gather data on logistics, content, and general feedback through post-meetup surveys, and honestly, the scores are really high, often above 90%.

However, instead of obsessing over raising an 88% to 92%, we focus more on qualitative feedback—what people actually say in their responses and in direct conversations. Sure, if the score were 70%, it’d be worth investigating, but when things are already going well, it’s more about understanding the nuances of what worked and what didn’t.

One area we’ve improved over time is our travel policy. When I first started, I would simply book plane tickets for people, often with rigid itineraries like a 6 a.m. Sunday flight, without caring about preferences. Now, we’ve created a much more flexible and generous travel policy. People can come earlier, stay later, do some sightseeing, and book flights that suit their personal schedules. We have a self-service platform for them to choose within a budget, and I just approve for logistics.

Our goal is to make logistics invisible. If logistics are visible, something’s gone wrong. We also aim to strike a balance in the meetup schedule—yes, we plan structured activities, but we give people plenty of free time. For example, during a week-long meetup, we might rent out a co-working space from Monday to Friday. It allows people to drop in and work as they would in an office, without the restrictions of a typical office environment.

Seeing people doing their regular jobs at a shared table in a co-working space is always a bit unusual for us, since we don’t have a central office. But this setup helps maintain the balance of work and socializing while reinforcing the core purpose of meetups: building relationships.

It’s interesting that you mention free time. A lot of companies tend to overload their meetup schedules from early morning until late in the evening, which is generally not advisable. It sounds like you’ve realized on your own that free time is actually one of the most important aspects of the meetup.

Absolutely. We are very mindful of that, and we recognize that this is still a work trip for people, many of whom have families. So, typically, we start things on Monday afternoon with maybe a town hall or Q&A session for the whole company, which lasts a couple of hours. After that, we have a company-sponsored dinner on Monday evening.

For the rest of the meetup—Tuesday, Wednesday, and Thursday—we just provide the environment, like renting a co-working space or meeting rooms in a hotel. It’s then up to the team leads or heads of departments to organize whatever work they need to do. People set up meetings amongst themselves, but I’m just providing the background and facilities for that.

Some teams may pack their schedules too tightly, but when we get feedback that this is happening, we step in. We talk with the team lead or department head and tell them, “Hey, stop doing that. It’s not productive. You need to allow more free time in the schedule. You shouldn’t be doing 9-to-5 back-to-back meetings—that’s ridiculous.” And that usually resolves things.

In practice, people might work a bit in the morning, grab lunch together, and work again in the afternoon. On one of the days, we usually have optional team-building activities in the afternoon, where people can sign up for whatever they want—or not sign up at all. Participation in anything, including the meetup itself, is never mandatory.

Of course, some people opt out entirely, whether because they just don’t feel like attending or they have personal reasons, like a guy who had a sick child and couldn’t come. We never question anyone’s reason for skipping. That said, 85-90% of people do attend at least part of the meetup, even if it’s just for a few days.

And those few days are worth it. We see a massive productivity boost afterward, which usually lasts for about a month or two. Then, we plan the next meetup to get things back on track again.

How long do you see the effects after a meetup last? And how do you keep that energy going?

Szoszo: It’s tricky—it really depends on the team. But generally, we see a productivity boost that lasts for a month or two after the meetup. We saw this especially during COVID, when suddenly there were no meetups. It was a hard time for us. I spent a lot of time canceling events that had already been planned, which was tough.

We tried to recreate some of the in-person dynamics online, but you just can’t replicate everything. Sure, you can do 100% of the work remotely, and I’m a big advocate of remote work, but forming meaningful relationships is just so much harder online than in person. That’s the reality.

It’s like the conversation we’re having now—why are we doing this over Zoom when we could be sitting somewhere nice with a beer, having a great conversation with no time limits? That kind of bonding doesn’t happen on Zoom. It only happens in person, and during COVID, we saw a dip in productivity that we couldn’t really counter. Only when we restarted traveling in late 2021 and early 2022, things shifted and we saw pre-Covid productivity and engagement levels..

Meetups are in our DNA. Our CEO, Alari, believes they are a very important part of our culture. And since he’s the final decision-maker, the one who controls the budget, the strategy, and the vision, it works because he believes in it. He also participates, even if just for a couple of days. Sometimes he flies out to join a team dinner or an event, like when the whole Toggl team, including Alari, was singing and having fun in a restaurant.

One of the big decisions we made was not to make meetups mandatory. We had internal discussions about whether we should, but in the end, we chose not to because it’s only a handful of people who can’t attend, and it’s important to respect that. Work-life balance matters.

People genuinely want to come. I think a big part of why it works is that we’re fortunate to have a CEO who really understands and values this.

New startups usually have this mindset from the get-go because they’re growing, hiring globally, and the internet makes that possible. But for companies that have been around for decades, there’s often resistance to switching models, especially from the top. And as any change manager will tell you, if there’s no real support from leadership, change won’t happen. It’s not enough to just say it on paper—the leadership has to actually follow through. If you were to switch to a company that’s hybrid or something like that, how would you convince the CEO to move to this model?

I don’t think you can convince someone who’s used to a very different model by just throwing numbers at them, like saying, “Hey, if you change to this, you’ll see a 10% increase in whatever.” I mean, I’m a numbers guy, but I don’t think you can measure this change in such a straightforward way. The impact becomes clear over time, like over a year, two years, or even five years, when you can look back and compare where you were and where you’ve gone.

What I would tell them first is to try it out. What do you have to lose? Yes, for many companies, budget is always a concern, but if you’re remote, you’re not paying for office space. You’re not paying, or only partly paying, for office equipment. You don’t have to maintain all that infrastructure. So, financially, it usually makes sense.

Plus, the money you save from not having an office doesn’t all have to go into retreats or meetups. Office space for a year is still more expensive than organizing meetups.

The way I see it, office space is a cost, but meetups or retreats—those are investments. It’s an investment with a return on investment (ROI). An office is just a sunk cost, pure and simple.

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Let’s say a company is remote or hybrid, but they don’t believe in retreats. What would you say to convince them otherwise?

First of all - try it. You’ve got nothing to lose. A good CEO is a visionary, willing to try things that others haven’t, and that’s how they make money. So, I’d say, use that same mindset for building your team and organization that you use for building your product. You’re likely not just a manufacturer, where remote work wouldn’t apply as easily. But in knowledge work, there’s flexibility.

Second, I’d encourage them to experience the difference themselves. Sit in on those in-person retreat conversations and compare them to a Zoom meeting. Participate. If the CEO or leadership doesn’t engage, it’s hard for them to see the value. Our CEO loves karaoke, and he’s out there with us, making a fool of himself in a fun, supportive way. It’s not forced—people stay because they’re having fun, building relationships, and bonding in ways that don’t happen on a Zoom call.

I can’t promise you a precise 17.5% increase in productivity because of retreats. I don’t believe in that kind of exact number when it comes to this. But I can say, from experience, there’s something magical that happens when people spend a few days together, having fun and bonding. Friendships form, and those relationships make a huge difference.

For example, in my PeopleOps team, I don’t just have coworkers—I have friends who are willing to go the extra mile, not for Toggl, but for me personally. That’s because we’ve shared experiences: we’ve done barbecues, we’ve gone paintballing, we’ve stayed up late talking about life. So when I need help in a tough situation, I’ve got people who are ready to jump in because of that personal connection.

These kinds of relationships can save businesses, increase productivity, and help companies thrive in ways that can’t always be measured by KPIs. So my best advice is to just try it and see for yourself. There's real value in it that can make all the difference during those critical moments when you need people to step up, and that’s not something that gets captured in a productivity report.

Without this kind of cohesion, when something critical happens, it can turn into a disaster. Fixing it would require a lot of money, time, and effort. But with a stronger connection, these disasters can be prevented, and you wouldn’t even know how much time or money you saved until after the fact. These are the hidden benefits people often overlook.

Exactly. It’s like soldiers in a platoon. They don’t go through all that for big political ideas or for their country, at least not in the moment. They do it for each other—for their comrades, their friends. That camaraderie drives them to take care of one another. And I think if you can create that same sense of connection within a company, it’s much easier for people to go above and beyond.

They don’t do it for the CEO or the higher-ups—they do it for their team, their friends.

People aren’t going to wake up in the morning thinking, "I’m going to work today to make the CEO richer." But they will show up if they feel valued, if they believe in the product or the company’s vision, or even if they’re just motivated by not wanting to let their team down. It’s about having a purpose, a reason to care.

In my role, people can’t help me with logistics because that’s my area. But they help in other ways. Sometimes it's by listening to me when I’m frustrated, which is crucial when you work with 130 people—there are always challenges. Having a team to support you makes all the difference, especially when you need to vent or figure out how to navigate difficult situations.

Team building isn’t just about the structured activities, either. It’s happening from the first greeting in the morning until the moment you leave. Every interaction builds the team, strengthens connections, and helps individuals grow.

And the bonus is, people get to travel, visit interesting places, and have fun. What could go wrong with that?

Which activities work best for the Toggl team. Which ones are always a hit, and which ones didn’t go as planned, even though you thought they would?

That’s a great question. When I first joined, the approach was pretty structured—we had one activity per meetup, with a budget of around 80 euros per person. We did things like boat trips, food tours, go-karting, excursions, and hiking. I remember organizing a scavenger hunt in Budapest for 130 people, and it was a hit. Everyone loved it!

The following year, I organized another scavenger hunt in Warsaw, thinking it would be a similar success. But we ended up with the exact same tasks as in Budapest—things like "take a picture of a yellow car." People were smart and reused their pictures from the previous year. I was furious with the company we hired, and we never did scavenger hunts again after that.

Now, we’ve moved away from having one set activity for everyone. Instead, we collect options and let people choose what they want to do. There are options for more active things like hiking or paintball, and for more relaxed ones like food tours. People can choose what suits them best. I remember one hike we did in Estonia in October—it was freezing and raining, and we were out there for eight hours. My clothes were soaked, and I was envious of those who had the guts to lie and say their legs hurt to avoid the hike!

Since we’ve made activities optional and given people multiple options, participation has increased. Most people want to be involved, but they appreciate having the choice. However, it’s getting harder to find new activities that fit everyone. We try things like cooking classes, but organizing that for 130 people is impossible. Still, activities where people create something together tend to have the best impact. They foster stronger connections and team bonding.

For instance, karaoke has become a tradition at Toggl. It wasn’t something I planned—it just started happening at every meetup. Last year, we made it official by renting an entire karaoke place, complete with dinner for 130 people. It was great. Some people just ate and talked, while others sang, and a few even went to McDonald’s because the food was “too sophisticated” for them.

When it comes to food, we used to let people pre-select from three options months in advance, but no one remembered what they chose by the time of the meetup. Now, we only go to places with buffet tables, so people can choose whatever they want on the spot. This way, we avoid logistical nightmares and cater to different dietary needs—vegans, lactose-free, gluten-free, you name it. Toggl’s team has been very understanding about food choices, and I always make sure to accommodate everyone.

The key is to let people choose their activities and meals so they can have the best experience. Forcing people to do something they don’t enjoy leaves them with regrets. It’s also important to remind people that it’s okay to take a break. We even put it in writing that if they need to go to their room to recharge, they should feel free to do so—no guilt involved. IT guys, in particular, really appreciate that permission. They would take breaks anyway, but now they don’t have to hide it.

Ultimately, if people feel good, they’ll do good work. That’s the big idea here.

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