How to Make the Most out of a Distributed Team Retreat (Without Breaking the Bank)

At TaxJar, we love working remotely. And we’ve created a team culture and strategies that we feel make us very successful as a distributed team. We work hard and have fun daily, and our team standups and our chats over Flowdock keep us connected.

Still, some of our most fun moments as a company have been our twice-annual get togethers. We call our retreats “JarFests” and we use them to set priorities and goals, bond, and just generally eat all the food and have all the fun. (Stay tuned to this spot for a blog post extolling the virtues of JarFest and retreats for distributed teams.)

But there’s an art to planning a remote team retreat without going overboard. Being a completely distributed team saves us a boatload of money on office space and other related costs, but we have big plans. And that involves putting the money we have in the bank to good use freeing the businesses of the world of their sales tax burdens.

So while it’s tempting to go big for our JarFests…

….we’ve opted to plan them in a budget-conscious way without sacrificing any of the things that make our JarFests work so well in the first place.

We have a few reasons for this:

• Our goal is “togetherness” — Yeah, I know that sounds like some hippie dippy bs, but our goal for our team retreats is to spend quality time together as a team. We can just as easily do that in an inexpensive hidden gem here in the U.S. (where we all live), as in some exotic locale.
• Bootstrapping is in our DNA –Most of us on the TaxJar team have started our own businesses in the past. All of us are accustomed to being scrappy, making calculated decisions, and keeping our operations lean and mean. Those same values extend to planning our team retreats.

Oh, and the big one:

• We are profitable! — We achieved our first consecutive profitable months within just three years, and we want to keep it that way. Like Mark, our CEO, mentioned in an earlier post, we’re transparent about our financials. We’ve all agreed that we want to maintain profitability and use our money in the bank to achieve our loftiest goals for TaxJar and our customers.

But before you think our team retreats are dreary affairs, not so fast! We have a few tricks up our sleeves to make our retreats just as fun as a transoceanic jaunt, but without breaking the bank.

How We Keep Team Retreats Super Fun without Breaking the Budget

Here are some tactics we’ve used in the past:

• We chose a central location — Our first three JarFests took place in La Jolla, CA. At the time, this was within driving distance for 3 of our team members, and within a short, low-cost flight for a few more. As our team grew (and team members pinballed around the country), we chose another central location, St. Louis, for our latest JarFest.
• We shopped around & asked for value adds — When you’re buying for a group, you can often find (or ask for) incentives and value adds. For example, meeting space is generally pretty expensive, but for two of our JarFests we were able to score a free meeting room, saving us a pretty penny on the overall cost of the trip.
• We used AirBNB (but for meeting space) — Since our last JarFest location, St. Louis, is better known for barbecue than team retreats, meeting space proved harder to find (though I discovered some awesome St. Louis co-working spots like this one in the process). We ended up renting a swanky AirBNB in the same building as our hotel. Better yet, the way our numbers worked out we were able to hold a contest and allow one team member to have the entire 2200 square foot place to herself (when we weren’t meeting there.)
• We travel in shoulder or off-seasons — We take our retreats in February and September, which happens to coincide with shoulder season in centrally located spots with decent weather. Timing is everything.

Grand Totals for our Last JarFest

In the spirit of transparency, here’s (rounded) what we spent on JarFest 4 in lovely St. Louis:

• Entertainment: $370
• Food: $2,600
• Hotel: $3,800
• Surprises: $130*
• Swag: $200
• Travel: $5,500
• Meeting Space: $1,300

Grand Total: $13,900

*I would tell you what the “Surprises” category involves, but it’s a surprise! You should come work at TaxJar to find out. 😉

For 12 team members, factoring in my wonky rounding, that comes out to right around $1150 per person. Not bad.

What’s Next for TaxJar’s Awesome Budget-Conscious Retreats?

Our goal for our next JarFest is to focus on what works best for us — spending time together as a team to focus on our vision and goals and to just generally bond — while still only spending ~$1,000 per team member.

You heard that here, folks. Check back here in February for my report on how we fared meeting that goal.

Meanwhile, we want to hear your thoughts. Do you hold the (totally valid) opinion that team retreats should be blowout affairs? How much do you consider your budget when planning a team retreat? What are your tips for planning an awesome team retreat? Let us know in the comments!