Managing a remote team in a startup: learnings from Woola
In the fast-paced world of start-ups, managing a remote team effectively can be a complex yet rewarding challenge. For example, here at Woola, our workforce is spread across multiple European countries, with some working from home, others preferring the office, and a factory team who cannot work remotely at all. Finding a balance that works for everyone is essential.
Here’s how we navigate this unique work dynamic and build a cohesive, efficient team.
1. Establishing clear communication channels & leveraging technology
One of the biggest challenges in remote work is ensuring smooth communication across different time zones and work environments. The right tools can make all the difference. While overcommunication can be a risk, we aim for high transparency — so when in doubt, we communicate.
Here’s how we make sure communication flows across our team:
We use a mix of asynchronous (Slack messages, project management tools) and synchronous (Google Meet calls, team meetings) communication. Some examples of rules we've agreed on regarding communication: email is only for external communication, and we never email each other internally. Slack channels are mostly public, and we generally aim to keep information flowing freely across the team.
We’ve also set clear expectations for response times. While there’s no strict rule like "respond within an hour," the general expectation is to reply as soon as possible, at most within a couple of hours during the workday. We understand the importance of focus time, but as a small team, we rely heavily on each other, so messages should be answered by the end of the working day.
To promote transparency, we hold regular meetings over video call. Every Monday, we meet for "Weekly Updates" to share what everyone’s been working on. We also host "Monthly Updates" (our version of an all-hands meeting) to review progress toward bigger departmental goals.
2. Creating a strong company culture
A strong company culture helps remote and in-office employees feel connected, even when they don’t see each other daily.
Here’s what we have put in place to make sure our company culture has space to flourish:
We organise virtual team-building activities and occasional in-person meetups. On Fridays, we block off time for a virtual coffee break — a space to chat about non-work topics. Sometimes, team members present photos from their recent holidays. At least twice a year, we bring the whole team together in Estonia for our Strategy Gaala (our version of a strategy day paired with some fun) to align on goals and spend quality time together.
We also make sure every employee feels heard, no matter their location. Once a month, our Chief of Staff meets 1-on-1 with each team member to check in on both work-related and personal topics, helping surface issues that might otherwise go unnoticed.
And when it comes to recognition, there’s no such thing as too much. We regularly celebrate each other’s wins to boost morale. Most of us are our own toughest critics, so a little public praise goes a long way. One example of this is our bi-yearly awards ceremony, where employees vote for each other in different categories, to bring out the stars that are shining especially bright.
3. Aligning schedules and workflows
Managing a distributed team means navigating different time zones, work habits, and personal preferences. To help coordinate efforts across teams and locations, we’ve established some internal rules:
We’ve agreed on core working hours (10 AM to 3 PM Estonia time) when everyone has to be available and reachable for work topics.
While we’re quite flexible with our time off bookings, any holidays longer than a week need to be requested at least 1 month in advance, so we can plan our team’s work accordingly. We also avoid taking long holidays during our peak business seasons.
4. Supporting both remote and in-office employees
Balancing remote and in-office work requires thoughtful policies and a flexible mindset. At Woola, we offer as much flexibility as possible while also acknowledging the realities of our business model and ambitious mission. While our office team works in a hybrid setup, our factory team, understandably, cannot.
If someone figures out how to move factory operations to a home office — huge kudos in advance (and please let us know as well!)
To support our remote employees, we:
Provide stipends for home office setups. This is mainly reserved for, and especially important for, employees abroad who don’t have the option to work from our office.
Ensure in-office workers have access to ergonomic, well-equipped workspaces. Every new hire receives a computer of their preference, keyboard, mouse, laptop stand, and external monitor.
Offer hybrid options to allow team members to choose the environment that best supports their productivity. Some prefer working from home, while others come into our cosy Tallinn office almost daily. This just means that everyone gets to decide how they work best, and which environment supports their productivity the most.
5. Bridging the gap with the factory team
Factory employees, who can't work remotely, may feel disconnected from the rest of the company. We work hard to maintain a unified culture, but we’re also realistic about the challenges.
Here’s how we include and support our team in the factory:
Share company updates regularly. Our Chief of Staff visits the factory in Paldiski to provide updates, ask for feedback, and hold 1-on-1 check-ins.
Celebrate milestones just like we do in the office — birthdays, work anniversaries, and new hires.
Offer a consistent benefits package, regardless of location. Everyone at Woola gets birthday PTO, three additional paid days off per year, stock options, and sports compensation.
6. Fostering trust and autonomy
In our experience, trust is the foundation of any high-performing team, especially a remote one. Some points we live by:
Micromanagement is a recipe for disengagement, especially in a remote setting. In fact, it’s almost impossible if you want to continue pushing forward. Who has time to wait for your manager to approve and control everything from afar if they can’t even look over your shoulder? Not us.
We set clear expectations and trust our employees to manage their work independently. We’ve hired talented, experienced professionals — true specialists in their fields — and we believe they’re more than capable of making the right decisions.
Encourage regular check-ins without being intrusive. In addition to the monthly 1-on-1 with the Chief of Staff, most department heads also have regular 1-on-1 meetings with their direct reports. We also operate with a truly open-door (or rather, open-message) policy. If something needs attention, we make sure to address it with the urgency it deserves.
When it comes to trust, consistency matters. If someone’s actions violate our shared values, we react and give them feedback on it. If it happens more than once, we also address it appropriately. At the same time, we don’t let one person’s mistakes shake our trust in the broader team or the systems we’ve built.
Final thoughts
A remote-flexible culture can thrive simultaneously with in-office and “in-factory” formats in one company. All you need to do is have the right communication, culture, and tools in place.
By embracing flexibility and prioritising inclusion, start-ups can successfully manage a diverse team and build a productive, engaged workforce, no matter where they’re based.
We’ve seen it work at Woola, and we wouldn’t have it any other way.
