Brian Bailey

Head of Product Strategy at 37signals, makers of Basecamp and HEY (and HEY World.) Find me elsewhere at and @bb on Twitter.
November 20, 2023

Make room for ambition

You start a new project. The pitch outlines the problem and boundaries of the solution. There's an appetite, like three weeks, that captures how much time it's worth investing. It's time to jump in. You add some to-dos. Have a kickoff call. Mock up a few approaches, throw together a dead simple UI, or spike a potential data model. All ...
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September 12, 2023

Strict scrutiny

The Betting Table is how product priorities are chosen in Shape Up. It’s essentially a planning meeting—priorities are debated, projects picked, and teams finalized—but, it still prompts a lot of questions. What’s so different? Let’s start with the basics. The meeting is three people: Jason (CEO), David (CTO), and myself (Head of Produ...
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September 4, 2023


You can’t have margin without constraints. At 37signals, we work in 6-week cycles. At the end of the 6 weeks, whatever we’re building has to ship. After the cycle, we have a 2-week cool-down where people can roam, experiment, and fix a nagging frustration or two. It's also a chance to slow down, reflect, and recalibrate. The cool-down ...
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July 1, 2023

Often, not always

Do you optimize for consistency or flexibility? Many of us are drawn to patterns and processes. When something goes well, we try to figure out how to repeat the success. “That project went great. Let's do the same thing next time.” When things go poorly, we look for which inputs led to the wrong output. Then, we introduce checkpoints t...
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March 22, 2023

Lessons in shaping

When I joined 37signals last year, I had been using Shape Up for four years, but I was eager to learn how shaping here differed from my own experience. I wasn't disappointed! Jason and David share invaluable feedback during shaping and at the betting table, as do the programmers and designers who take a pitch and turn it into something...
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July 29, 2022

The pizza or the toppings

Product strategy is continually asking, What is the pizza, and what are the toppings? What defines a pizza? At it's core, it's a round base of dough baked with a topping of tomato sauce and cheese. If you're opening a restaurant and want to be known for great pizza, that's where to start. Experiment over and over again until you perfec...
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July 17, 2022

It's okay not to know

From the start of my career, I've known the products I've worked on inside and out. Not only how they work, but why they work that way—from how one feature intertwines with another to the reasons others were never built. Joining two startups while the employee count was still in the single digits made it easy. I was there from the star...
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June 2, 2022

New job, same desk

One twist of remote work is that when you get a new job, you don't get a new office. I started at 37signals last month. We make Basecamp and HEY (and HEY World!) The company is fully distributed, with employees around the world. I’m working on product strategy from my home office in Austin. Which happens to be the same home office I wo...
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