Company Retreat Planning for a Bootstrapped Team

Companies like Automattic and Buffer have frequent all-company retreats in exotic destinations around the world. Moving hundreds of team members …

by Ryan Sullivan


10 min read

Companies like Automattic and Buffer have frequent all-company retreats in exotic destinations around the world. Moving hundreds of team members from all over the globe to one locale for a company retreat is a pretty awesome feat of logistics. Just figuring out how many pizzas to order requires some form of advanced calculus!

But what if you don’t have those deep venture-backing-lined pockets? What if even getting one person on your team to work part-time on planning would be a massive strain on your people power? That’s the reality of planning a company retreat for a small, scrappy, bootstrapped team.

The good news is that it is possible to hold a fantastic event for your team without breaking the bank or skipping sleep for the months leading up to the retreat. It takes some common sense, and probably more elbow grease than those Silicon Valley folks need to apply, but it’s definitely doable.

Disclaimer: This guide is intended for teams of 5-25. I’m not sure that any of this scales beyond that, so if you’re working in a corporation of 800 and are looking for helpful retreat planning tips, your mileage will vary with this particular piece of content.

Why have a company retreat at all?

There are countless advantages to being a remote company with a distributed workforce, but it’s not all roses. You can get lonely or feel isolated. Your imposter syndrome can get out of control because you think you’re the only one struggling. You miss out on the energy that being together as a group can bring in a more traditional office space. The small talk of what you did the night before can get overlooked.

Fight against the negative energy

There are ways to fight against those things every day using chat and frequent check-ins like the ones we use in Basecamp, but nothing seems to do the trick more quickly and efficiently than a face to face meet up with the whole team. That’s why even though a remote structure works incredibly well for our team most of the time, we like to take any chance we can get to get together.

Conferences are great for getting together, but they’re usually niche events and it doesn’t make sense for everyone on the team to attend. It can also be tough for people to be away from home for an extended period of time. By the time you add 2-4 days of team time to a 3 day conference, people feel stressed out and overwhelmed about not being at home.

At our company retreat this year we’re going to have a session dedicated solely to talking about what to do when we find ourselves in a tough spot. Where’s the button we push or the ripcord we pull when we’re in a pickle and need help getting back on track?

Get out of the business

The reality is that we need time to step away from our every day work to really evaluate what we’re doing well, and where we can get better.

Man on a tall ladder looking over clouds

We use our daily routine as an avoidance tactic. We ignore the tough questions by burying ourselves in the little day to day things that don’t drive our business or make a big impact because busyness is a place where we feel safe.

You have to spend some time in the clouds like Gary Vaynerchuk recommends.

Retreats give us a chance to step away and ask the hard questions, and also take the time necessary to process and think about the answers in a place that isn’t inundated with Pings, DMs, Tweets, or Pokes.

Put the TREAT in Retreat

I know it’s a huge ask to have people leave their families and come to a remote location for a few days, and I also know that my team is the hardest working group in existence. Because of that I really try and make our annual retreat an experience they look forward to, and not one they dread.

If there are any places where I blow the budget a little bit, it’s on things that directly make the retreat more enjoyable for my team, and give them experiences that they won’t forget.

At our last retreat we brought massage therapists on-site. I wanted to give employees the gift of relaxation. I also bought everyone on the team some custom Bose headphones cause I knew that was something they’d likely use every day and would make their lives better. Another thing we did was stay at a really swanky “cabin” (there aren’t enough finger quotes in the world because although it was technically a cabin, mountainside mansion is probably a more accurate description) that was a place they’d likely never see otherwise.

What did our team say about our last retreat?

Here’s a quote from our Director of Technology, Rob Neu, about our last retreat:

When we went to Park City in 2015 I figured the combination of flying on a metal death tube and being around other people was a recipe for real dog ? sandwich. I’m never pleasantly surprised, so I won’t go that far, but I will say the retreat sucked a lot less than I thought it was going to.

This year we’re renting ATVs and spending a day in the desert blowing through sand dunes. It’s not the cheapest activity, but it’s one that the team can’t experience many other places in the world, and definitely one they’ll never forget.


If you’re doing the mental math and thinking “wow, multiply all this stuff by 10 or 15 people and this is starting to add up”, the truth is that while it wasn’t super cheap, it’s way more affordable than you’d think.

How to save money when planning a company retreat

Boy putting money into a piggy bank

Your investment will pay off

First of all, stop thinking about a retreat as an expense. It’s an investment. Use time well and deliver a great experience to your team, and nothing will grow the relationships in your squad more quickly. Building trust advances the work more than anything else you can do in your business. Not to mention we still joke all the time about things that happened during our last retreat.

Second, having a remote team means that every day you’re saving money on overhead like office buildings and all the associated costs attached to that. As you plan out your year, delegate a big percentage of money you would have spent on offices and physical infrastructure to your annual retreat.


I’m glad you asked. Here are some of the key things we do every year to save money on our annual retreats.

Plan your retreats outside “peak times”

Fire pit in the woods in Park City

That $12 million dollar “cabin” we stayed in that had private rooms for everyone? It was $1200 a night because we weren’t in the middle of ski season. While that might sound pricey, that’s only $100 per person, per night, which is an amazing rate for Holiday Inn Express let alone an incredible mansion in one of the most sought after resort areas in the world.

This year we’re going to St. George, Utah. It’s another beautiful resort town near several National Parks, and we’re visiting 1 week outside “peak time”. We found some amazing villas on a golf course for about the same price we paid in Park City. You can usually tell when peak times are by doing a few google searches, but the best indicator is rates. From one week to the next prices could double or even triple. Peak season in St. George starts April 1st ?

Quick tip: Book early. Sometimes if you book early enough the multiplier for peak dates hasn’t been applied to the online reservation system and you can get off peak rates during peak times!

Negotiate negotiate negotiate

Group at restaurant table celebrating

This seems simple, but not enough people do it. For any team activities or restaurants you go to, always negotiate a group rate. Think of it from the business owner’s point of view. They can either have 12 guests visit and order extras like wine, appetizers, and desserts. Or they can try and sell those 12 seats to people who aren’t in celebration mode. The total ticket amount and guaranteed business means a restaurant manager will happily give a healthy discount to have you visit their establishment.

There are plenty of other opportunities to negotiate as well. When buying custom swag or booking your accommodation, just ask if there’s any kind of incentive available. Typically sales people have some margin to work with, and if your company can be the beneficiary, all the better.

Quick tipPhrase it like a question so you don’t come across as a tool. “Do you have any deals or incentives for groups going on? We’d love to get in on any promotions!”

Booking early isn’t best when it comes to flights

Booking flights definitely requires some logistics, but it also requires a time investment to get good flights for a reasonable price. While I’m all for saving money, flights are not a place where I like to skimp.

Sending an employee through four rural airports in order to save $64 is not my idea of “savings”. (See note above about treating your employees well) That said, you can keep track of flight pricing trends using a tool like Hipmunk so you’re sure to buy at the best time.

We used a service called Flightfox for one of our reunions. They take care of all flight booking for you. Kind of like a virtual travel agency. It did the trick and took the burden off of us for booking, but it happened very quickly (same day), and the flight prices were just ok, not great. Being patient and booking flights on our own has ultimately been a better experiences. We get the flights we want at a price we’re happy with.

Quick tip: If you search flights directly on the airline website, make sure to use incognito mode until you’re ready to purchase. They’ll adjust your pricing based on how you use their website. For example, if you visit the site multiple times per day, they know you’re anxious to book, so they’ll likely increase the price. All the airlines do it now. Yet another reason to use a tool like Hipmunk to browse and track for you.

Spend less on food than you think you should

Homer Simpson eating mayonnaise from the jar

Food has ended up being a footnote during our past retreats. In fact, after our Park City retreat we donated about $500 worth of untouched groceries to the local food bank because we didn’t end up using them.

People tend to graze and snack instead of having full meals. Think of your eating habits at home. It’s pretty rare that we all have three prepared meals in a day. This year we’re going to light on groceries. We’ll stock the villas with continental breakfast foods and lunch items for salads and sandwiches, but that’s about it. Everything else will be snacks and beverages, and then in the evening we’ll go out to eat at restaurants.

Quick Tip: Buy less food, and be close enough to civilization that you can supplement during the week if needed.

That’s a wrap

Being involved in the planning of the company retreat is legitimately one of my favorite things I do every year. Even though it requires a decent amount of effort, it’s extremely rewarding for me to see everyone get together and have a good time.

If I had one parting thought it’d be to think about the people the event is for and plan it for them, not the company. Being mindful of your team, what’s important to them, and showing them your gratitude will come back to reward you tenfold as you move your business forward in the year to come.

Have you been on a corporate retreat? What was it like? Fantastic? Or do you have horror stories to share? Hit us up in the comments!

Ryan Sullivan | VP, Technology

1 Comment

  • M
    MiaGray 2 years ago

    Ah, the alternately celebrated (or possibly dreaded) company retreat. I have planned three company retreats for my team at Cirrus Insight. Our last two retreats were in Nashville and Atlanta, and this September we’re going to Chicago. On these retreats, my team and I have had a lot of fun and laughs while getting a lot of work done, too. So what goes into a successful company retreat? And how do you strike the right balance between work and fun?

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