How we planned our Norwegian team offsite as a remote startup

We just returned from our sixth and best team offsite to date set in the scenic fjords of Norway. If you're wondering why we chose such an obscure destination, it's because we had an opportunity to rent out the one-of-a-kind landscape hotel where the movie Ex Machina and the HBO series Succession were filmed.

But we're not here to brag about our latest adventure.

Instead, after organizing six offsites in three years, we feel like we've finally found our groove and have some insights worth sharing. We're hoping that by writing this retrospective, we'll help other remote teams avoid much of the trial and error we had to go through when we first started planning offsites.

Why we go on offsites

Offsites are expensive, time-consuming, and difficult to plan. But just like raising children, the juice is worth the squeeze. Before we get into the planning process, let us share some of our reasons for investing so much in two team offsites per year.

The first reason is that they're fun!

If this sounds obvious to you, consider yourself lucky. For most people with office jobs, the word "offsite" refers to a two-day seminar in a Sheraton meeting room learning about the conjoined triangle of success.

It doesn't have to be that way. Being a small, young team has enabled us to visit destinations such as Norway, Santa Fe, Ireland, Buenos Aires, Lake Como, and Tulum. And because we're a remote company, simply spending time together fosters natural team building without any contrivances.

The second reason is that offsites are invaluable to recruiting, onboarding, and retaining a high performance team as a remote company.

Talented individuals want to work for companies where they'll be surrounded by other talented individuals helping them both grow and develop long-term relationships. We're as bullish on collaboration software as anyone, but Slack, Zoom, and email just don't cut it for cultivating these kinds of professional bonds.

As a result of our offsites, however, it's safe to say that every member of the team has made genuine friendships within the company that will outlast their tenure at Readwise. Speaking of tenure, the offsites certainly don't hurt retention either!

The third and final reason is that offsites offer an opportunity to align the team and get everyone (excitedly) rowing in the same direction.

In writing about how Jeff Bezos ensured his company's strategies were universally understood within the Amazon organization, Eugene Wei came up with a test of how strategically aligned a company is: "Walk up to anyone in the company in the hallway and ask them if they know what their current top priority or mission is. Can they recite it from memory?"

In a remote company, this kind of alignment tends to drift quickly. The offsite is the perfect opportunity to course correct, ensuring everyone on the team understands what we're working on and why. You can feel the effects of this alignment immediately following each offsite. Those first few months are without fail the most productive of the year.

There are other benefits, of course, but fun, team building, and strategic alignment are those most important to us.

Let us now share our planning process in the hope that you can adapt some of it to your situation.

How we plan offsites

If you've ever organized an international trip with a group of far flung friends and family – each flying in from a different place at a different time, and each with their own travel preferences – you have a taste for what it's like to plan a team offsite for a remote company. Now imagine that only one or two individuals are tasked with the responsibility of ensuring a good time for five times the number of travelers. That's offsite planning.

It's taken us some trial and error to figure out how to manage all this complexity. Fortunately, we've finally developed a repeatable process that works reliably enough to be worth sharing. Like all startup advice, you probably don't want to cargo cult exactly what we do for your own situation, but we hope this example serves as a helpful starting point in developing your own process.

At a high level, here are the steps we follow for each offsite:

• Hold potential dates after polling the team on availability.
• Set destination parameters after surveying the team on preferences.
• Source potential venues with availability on those dates within those parameters.
• Let the team vote on a handful of narrowed down options.
• Reserve the venue.
• Book flights and ground transportation.
• Plan activities and meals.
• Finalize the itinerary and share with the team.
• Design a commemorative pin.
• Buy and brand location-inspired team swag.

We'll walk you through each of these steps using our Norway offsite as a case study.

But first there's one other very important consideration you must figure out: who within your company will lead the planning process?

Who is responsible for offsite planning

In a traditional corporate setting, the burden of travel planning is typically shouldered by an executive or administrative assistant. In a modern tech company with fewer than 50 employees, however, admins are rare. (At least, it's our opinion that they should be rare.) This means we need to pull someone off their day job to organize the offsite. But who?

After much experimentation, we've found that the ideal personality for managing offsites is the kind of detail-oriented person who knows their way around a spreadsheet, tricks out Notion dashboards in their spare time, and will herd cats to meet a deadline. Basically, a recovering investment banking analyst and/or MBA.

In our case, that's our Head of Bizops Fernando del Campo.

Of course, there's so much "culture" that goes into an offsite that the founders must remain involved at the visionary level, but hopefully you have someone on your team who can serve as operator.

You might be wondering: Can't you just hire an external resource to lead offsite planning?

We've tried that – multiple times – and we just haven't been able to find a solution that works. We've tried traditional travel agents: they just want you to go to a branded resort hotel where they'll get a commission. We've tried YC-backed offsite planning startups: they just want to jam you through an inflexible "tech enabled" productized service. And we've tried freelance offsite consultants: they just want to imagine warm and fuzzy team building activities rather than handle messy travel logistics.

If your company is approximately our size, our advice is to just figure out how to organize the offsite on your own. To help you up the learning curve, let's now get into the details of our process.

Step 1: Hold potential offsite dates

The first step to finding a suitable venue is knowing what dates your entire team is willing to travel. Like all travel planning, the sooner you start this process, the more options you'll have.

We shoot for one offsite approximately every six months, so after returning from Santa Fe, New Mexico in October 2023, we knew the next offsite would take place in April 2024, give or take a month. To identify potential date ranges, we send the team a Typeform survey around this date where each person marks particular days as "ideal" or "dealbreakers".

Each and every person on the team must complete the survey before you can confidently extract potential date ranges, so part of this process is aggressively nudging the stragglers. But once everyone has submitted, you hopefully have at least two weeks that emerge as candidate travel dates. For our Spring 2024 offsite, we had the weeks of March 18th to 24th and April 21st to 28th as candidates.

Step 2: Set destination parameters

The next step in sourcing venues is setting some search constraints.

One unexpected obstacle we ran into when planning our first few offsites was the paradox of choice. It's hard to find a venue that feels right when you're searching across all of Europe or all of the Americas. To focus the search, we have the team vote on what kind of destination they'd like to visit next.

We do this by imagining a variety of vibes with colorful labels such as Urban Getaway or Coastal Oasis or Mountain Retreat. We then generate a cover image for each and add them as a ranked-choice vote in the same survey where we poll for availability.

For our Spring 2024 offsite, the top two preferred vibes were Coastal Oasis and Mountain Retreat.

Step 3: Source venues with availability within those parameters

With dates and parameters, it's much easier to search the internet for potential venues that will delight the team. For our spring 2024 offsite, Fernando identified a half dozen options and then worked with Dan and Tristan to narrow it down to two: The Pine Cliffs Hotel in Algarfe, Portugal for Coastal Oasis or The Juvet Landscape Hotel in Valldal, Norway for Mountain Retreat.

Step 4: Let the team vote

Time for another Typeform survey. You could of course get away with making the final call at the leadership level, but we find that involving the team makes the entire process more fun.

As part of filling out this survey, we ask everyone to first check potential flights to each destination to ensure they're factoring the pain of travel into their decision.

Given how hard it is to get to Ålesund, Norway, which sits above 60° latitude (farther north than Iceland) and requires at least 20 hours of travel for those of us in the Americas, we thought there was no chance that destination would win. But lo and behold, the team overwhelmingly voted for Juvet Landscape Hotel. Another virtue of the survey process.

Step 5: Reserve the winning venue

Once the team has voted, you should swiftly put down a deposit to lock the venue. Contiguous blocks of space for a large group can be hard to find and there's nothing more frustrating than having to start over because another group moved faster than you.

As an aside, we've tried all kinds of different venue types for our offsites. In Tulum, we stayed in a large Airbnb. In Lake Como, we rented a villa. In Buenos Aires, we took over a block of city hotel rooms with a nearby "party house" Airbnb. In Ireland, we rotated between a boutique hotel in Dublin and a resort hotel in Kerry. In Santa Fe, we stayed at a resort hotel with detached casitas.

Each accommodation type has its various pros and cons, but on this Norway offsite, we finally found our Goldilocks venue that's just right. Until our team is much larger, we're going to exclusively look for venues that pattern match to Juvet Landscape Hotel:

• 20 to 30 beds so we can rent the entire property
• Professionally operated (in contrast to many Airbnbs)
• Architecturally significant
• Communal meals served onsite
• Dedicated meeting space for our founder presentation and hackathon

Fernando has started building a directory of these venues. If you have any suggestions for us or want access to that list, please feel free to reach out!

Step 6: Book flights and ground transportation

Immediately after securing the venue, you should push the team to block their calendars and quickly book flights without hesitation as the decent options will only disappear while prices only go up.

We've tried leveraging a professional travel agent to streamline the flight booking process, but discovered it added more overhead than it saved. Instead, we find it's easiest to generate virtual credit cards and just let the team book their own flights within certain arrival, departure, and cost guidelines.

Finalizing flights is another step that requires a little cat herding, at least in our case, because some team members will inevitably want to tack on a bit of sightseeing before or after the trip. After all, many of them will be traveling for twenty plus hours to an international destination they're unlikely to revisit any time soon. In the case of Norway, more than half the team gathered in Oslo the weekend before to explore the city.

Once flights are set, you can then coordinate ground transportation. In remote destinations, that requires renting cars. In urban locations, you can just rely on public transportation and taxis.

Step 7: Plan activities and meals

At this point, the upcoming offsite has now taken shape and finalizing is just a matter of finishing touches. The first of those are the activities and group meals.

This part of the process was unusually challenging for the Norway offsite because late April is still shoulder season in the fjords. Many restaurants aren't yet open, it's too warm for most winter activities, and too cold for most summer activities. But Fernando worked through it with some help from the staff at Juvet and our Norwegian friend of Readwise, Aurora, and we ended up going on some great excursions including a boat tour of the Geiranger fjord, a snowshoe hike to the top of a mountain, a kayak tour of the fjord, a gondola to the Rampestreken viewpoint with scenic lunch, and of course some sauna and cold plunge opportunities.

Step 8: Finalize itinerary and share with team

Once we have the activities and meals figured out, we can then slot in the two outstanding cornerstones of our offsites: the founder presentation and the hackathon.

The founder presentation is a ritual where we tell the story of how our team formed as well as deploy the strategy of the company. The team formation narrative is especially fun for us because almost every colleague was previously a Readwise user before joining as an employee. One of the unique benefits of working on consumer (in contrast to B2B)!

The hackathon is a daylong event where people team up to hack on fun, creative projects we don't ordinarily have time to prioritize culminating with presentations to the entire group. Aside from fun and team building, the hackathon has inspired many of our favorite features such as text-to-speech, Ghostreader, and Weekly Wisereads.

The offsite is now fully planned!

To build hype and ensure everyone prepares appropriately, we like to assemble the itinerary into a handsome document that can be shared with the team.

Step 9: Design a commemorative pin

Given how core offsites have become to the Readwise culture, we've made it a tradition of designing a commemorative pin celebrating the particular destination for everyone who attends.

The original design direction was to style the pins after those stylish, retro US National Park posters you might see framed in someone's house. Alisha Giroux translated that vision to the medium of enamel pins better than we could have ever imagined.

Our Norway pin even glows in the dark!

Step 10: Buy and brand location-inspired swag

The final cherry on top of each offsite is some limited edition Readwise-branded swag often embodying the spirit of the destination.

In Ireland, we gave out embroidered Stutterheim raincoats and chunky Blarney Woolen Mills fisherman sweaters. In Santa Fe, leather weekender bags and alpaca blankets.

In keeping with the Succession theme of Juvet of the latest offsite, we commissioned black cashmere baseball caps: the epitome of quiet luxury, as sported throughout the series by Kendall Roy.

In case you're wondering: no, we didn't actually spend $500 on the authentic Loro Piana hat.

How much do we spend on offsites

Candidly, we hesitated to write this retrospective because we feared it might give the false impression that we're somehow living too large. The truth is that Readwise is a bootstrapped company that has never raised venture capital and therefore runs extremely lean. In fact, my cofounder and I worked on Readwise for three years before we paid ourselves a single dollar.

The reality is that two fun offsites per year costs us less than half of what we'd spend colocating year round in an office meaning we still save money relative to a traditional company.

In a former life, I worked in commercial real estate private equity investing exclusively in office buildings. As a result, the rules of thumb for how much money a typical company spends on office space (including extras like internet, furniture, and coffee) are etched into my brain. In a coastal city such as San Francisco or New York, the annual cost might start at $20,000 per employee before you layer in big tech extravagances such as catered lunches and stocked refrigerators.

Meanwhile, we spent a shade more than $4,000 per person on the Norway offsite, which is actually higher than average because it was set in Europe. In the Americas, we typically budget more like $3,000 to $3,500 per person. This results in approximately $7,500 per employee per year in offsite expenditures, or less than half what we'd be spending on an office in a tech hub.

Ultimately, however, it's not about cost. Readwise as a company — that is to say, the team — simply wouldn't exist as it does today without offsites.

Conclusion

That's our process. We hope you find some of it helpful in planning your next team offsite. If you have any questions or would like us to go deeper into specific topics, such as our founder presentation or hackathon, please feel free to reach out and let us know.

As mentioned in the introduction, Erin made an amazing video showcasing the Norwegian offsite if you want to see all of the above in action.

Also, if you want to join us on future offsites, we're hiring :)