5 Insights About Remote Team Learned During A Recent Team Retreat

Our seven-person team at Tiller Money is almost fully remote.

I would say “fully remote,” but two of our developers (Tim and Brasten) often work together at Tiller’s office at WeWork in Seattle. Another developer works outside of Seattle, our founder lives in the Methow Valley, our Customer Success lead lives in Asheville, our Project Manager lives in Spain, and I live in Vermont.

A couple of weeks ago, our entire 7-person team gathered in Seattle for a week. Our agenda was ambitions but not overpacked. A day at our team office at WeWork, an evening of bowling games which gave several of us a chance to introduce our families and get them to mingle, and a special day on Bainbridge Island.

Our agenda was packed. We talked about our core value prop, we talked about our road map (with sessions dedicated to our ongoing Excel project), and technical discussons about

marketing positioning

we know one day the Tiller team might now all fit in one conference room.


Our core value at Tiller is “money matters because life matters more.” To that end, while our work is massively important to us – keeping us profoundly engaged – so is spending time together as a team. Life matters more. It’s important to make time for non-work related connection and communication.

to that end, our retream

For a Remote Team, More Communication ≠ Better Communication

Our small team has daily standups, uses Slack profusely, and has frequent scheduled one-on-one calls. We also have pop-up calls to discuss progress on various initiatives, such as our upcoming Excel integration and Small Business and Tiller Budget templates.

 It’s Impossible to Overcommunicate About Overcommunication 


Teambuilding Exercises Are Underrated

I admit I’ve been a bit cynical about teambuilding exercises. I have too many flashbacks to trustfalls and wishy-washy doubtful successercises from the early 2000’s. (I cringe even as I type that portmanteau).

Some Discussions Still Work Better in Person

Trust is the Most Important Value


Start Your Free Trial

Try Tiller free and track all your accounts in one place, always know where your money goes, and confidently plan your financial future.

Tiller Money

Tiller Money

Your financial life in a spreadsheet, automatically updated each day.

Leave a Reply