Brian Bailey

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