Day in the Life of a Remote Company: Tortuga

The possibilities are endless when it comes to setting up shop as a remote-first company. Take Tortuga as a stellar example. This month, we spoke with their co-founder, Fred Perrotta about what it’s like to sell tangible products as a distributed team. Tortuga helps travelers avoid the cost and hassle of checking luggage with carry-on-sized travel backpacks.

As much as they are advocates for travel, Tortuga also champions for remote work through their writing, both as a company and as individuals, and through speaking at travel and remote work conferences.

“When we choose partners to work with, we don’t just focus on travel; we also work with groups like Location Indie and the Rural Online Initiative to bring location independence and remote work to more people.”
–Fred Perrotta, Co-Founder

As a distributed team of 11 that spans across 9 cities in 3 countries (US, Canada, and China), how do they manage their operations and function as a company? Find out below!

Why and how did you decide to go remote?

“By the time that we started to hire employees, we had been working remotely for years. We decided to make it official, encode it in our values, and hire for skills and fit, not for location.”

We went remote by accident. When my co-founder and I were starting the company, we lived in different cities. I was working at Google in San Francisco, and Jeremy was at film school in Los Angeles. We started the business as a side project. We did not intend to move to the same city and rent an office.

When we needed freelancers, we hired whoever we could afford on Upwork regardless of where they lived. By the time that we started to hire employees, we had been working remotely for years, and companies like Basecamp and Buffer were writing about their success with a remote set up. We decided to make it official, encode it in our values, and hire for skills and fit, not for location.

How is Tortuga structured?

Historically, we’ve been a flat organization with everyone reporting to me due to our small size. However, we recently hired a General Manager to help build out our team and coaching infrastructure. Our next step is to grow into a “team of teams” rather than a completely flat org. Each team will have its own Coach (what we call a manager) who will report to the GM.

What does a typical day look like at Tortuga?

Our team spans both North America and Asia so one continent’s day ends when the other’s begins. We’ll start at the end of the day Pacific time.

6pm As the workday is ending on the west coast of the US, the day is beginning in China. Our Production Manager heads to the factory to check on the latest samples and ensure that our current production order is running smoothly.

5am Evening in China is when our east coast team in North America starts their day. Teammates in the US and Canada respond to customer emails that came in over night, put the finishing touches on our latest gear guide, write copy for our next product launch, design a product that may be two years away from market, and schedule 1:1s with their direct reports.

8am Midnight in China. Late morning on the east coast. The day begins on the west coast. Our teammates in California and Washington are talking to our podcast partners, designing a new homepage for our website, and forecasting sales for the next holiday shopping season.

6pm As the day draws to a close on the west coast, it’s 9am in China. A new day begins.

How do you address common remote challenges for your employees?

“The real benefit is spending time together in person. Retreats help to bring us back together. They’re also an important part of onboarding new hires. We can nurture relationships online but we need that in-person time to start new relationships.”

Communication and visibility are the biggest challenges for us. Every team member has, at a minimum, a weekly video 1:1 with their Coach (manager). Many of our team members also have regular 1:1s with peers. For example, our Industrial Designer and Web Designer meet regularly despite not being in the same team meetings.

A combination of 15Five and Slack has helped us to improve communication and keep everyone apprised of everyone else’s work. Every Friday in 15Five, we update the progress on our OKRs and say if we’re on track, behind, or at risk. Then we share what we accomplished that week, our priorities for next week, and the biggest challenge we’re facing in our work. 15Five delivers this report to each person’s Coach where they can add comments. The updates are also shared to Slack so that the team can see what everyone else is working on.

Outside of our daily/weekly processes, we use biannual retreats as a way to bring the entire team together in person. We have talks and working sessions during the retreat, but the real benefit is spending time together in person. Retreats help to bring us back together. They’re also an important part of onboarding new hires. We can nurture relationships online but we need that in-person time to start new relationships.

Aside from working sessions, we always do a team activity on the first day, schedule big team dinners each night, and often travel together before or after the retreat when we meet outside the US. Our previous retreats have included Montreal, Lisbon, New Orleans, and Prague.

What kind of benefits do you offer your employees to ensure they are comfortable in their role and working remotely?

“Documentation is important, but you also have to ask and talk to your team about how they’re making the transition. This responsibility falls to their Coach and new hire buddy.”

We provide new hires with a “remote work set up” bonus for gear, but I don’t think that benefits are the best way to ensure people are comfortable working remotely. Instead, we provide guidance through our internal wiki and from teammates. Since we started growing the team, we have written advice for new hires on how to maximize productivity and how to avoid the pitfalls of remote work. Everyone on the team has contributed their thoughts on productivity and work/life balance.

We encourage people to be mindful of how they spend their newfound time and flexibility. For example, remote work can be isolating, so we suggest getting out during the day to meet a friend for lunch or to go to the gym. We let our team know that it’s okay to have some busier days and some shorter days. They no longer need to sit at their desk for a set number of hours or to try to look busy when things are slower. Even more importantly, we discuss all of this with them. Most of our teammates were new to remote work when they joined, so they had an adjustment period. Documentation is important, but you also have to ask and talk to your team about how they’re making the transition. This responsibility falls to their Coach and new hire buddy.

What cultural practices do you proudly promote?

“As a travel company, time off to recharge and to explore the world is important to us.”

We put a heavy emphasis on autonomy and allowing individual contributors space to do deep work. Remote work lends itself to deep work, but not everyone takes advantage of this structural benefit. We want Tortuga to be a place where people can do the best work of their careers.

We emphasize communication and documentation for projects so that everyone knows what we as a team and they as an individual should be working on. Then we minimize meetings to create space to do deep work. The last piece is to emphasize that Slack and email are asynchronous communication tools and that quick replies are not expected. We want people doing the work, not checking Slack.

To counterbalance this deep work, we have weekly video 1:1s, biannual retreats, and unlimited vacation policy. As a travel company, time off to recharge and to explore the world is important to us. Traveling is the best way for us to experience the same problems as our customers so that we can figure out how to solve them. Our vacations are also research.

Trusting employees is a big part of hiring remote candidates. How do you ensure your team is staying on task and engaged with their work?

We use Asana as our “single source of truth” for projects and 15Five for weekly status updates and for tracking progress towards our OKRs. 15Five also has a question to poll our team’s mood or feeling each week so that we can look for red flags and monitor changes.

How do the current tools you use serve your employees?

Remote teams must be intentional about using communication tools and creating processes to remain aligned and to fill in the “gaps” of communication that would work in an office but may get missed when working remotely.

Our tool stack should be lightweight but feel indispensable. Work should feel easier after we add the right tool. Our tools should never feel like a pointless task one has to do for someone else’s benefit.

We want our tools to serve our employees by making their lives easier. They should always know where the information they need is or who to talk to about a given issue. They should always know what’s going on across the company even if they’ve never spoken to anyone about it directly or attended that team’s meetings.

Tool Stack:

Asana is our single source of truth for shared projects, individual OKRs, and to do lists. Before the quarter starts, we add our projects and OKRs into Asana so that we can focus on executing during the quarter.
15Five is where we track OKR progress, share weekly updates, and manage biannual reviews. We like 15Five because it connects the week to the quarter to the biannual review.
Slack is our watercooler. Yes, everyone uses Slack but not everyone uses it well. We put an emphasis on Slack communication being asynchronous. We want our team to turn off notifications and to log out of Slack when they're in deep work. Our best practices and recommendations are all documented in our internal wiki so that new hires read this on Day 1.
Traction is an important tool for us even though it isn't software. Traction is a book that documents the Entrepreneurial Operating System. The planning processes and meeting structures outlined in the book have helped us to improve our planning and problem-solving.

What advice do you have for companies who want to go either fully remote or hybrid?

Going fully remote is probably easier than being a hybrid. For a remote team to succeed, the company must be built around asynchronous communication and extensive documentation. Having an all-remote team, rather than a partially-remote team, is a stronger forcing function. You would never build the systems necessary to work remotely unless most of your team is remote. Then those systems become vital to your survival and success.

Why do you believe remote work is here to stay?

Decentralization is the future. Working remotely will make us both happier and more productive, two variables that aren’t always correlated. The colocated office is a remnant of top-down, command-and-control organizational design leftover from the industrial era. Remote work is a more humane way to work as it allows us to integrate work into the rest of our lives rather than forcing us to build a life around our work. We should each get to live where we are happiest and work where we are most productive. Individuals, not their employers, should dictate the terms of their lives.

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