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In the early days of Segment, right after we crossed $10m ARR our growth decelerated 8x from 300% yoy to 40% yoy in 6 months. What the hell happened? How did we reaccelerate back to 100% yoy? A thread 1/18
At the surface, everything was burning. Customers were churning off our highly profitable Redshift data loader for cheap alternatives. A new competitor was killing us on mobile-first deals. The sales team was getting incredibly demoralized. 2/18
I felt like I had about a quarter to “figure it out” before everyone started bailing. I was panicking. 3/18
One day I was walking through the office, head down thinking and worrying, when suddenly our HR advisor @Rbeforel and CFO @jburkland ambushed me and pulled me into a conference room. 4/18
“Nobody knows what they’re supposed to work on, Peter.” What?! 5/18
I told them the goals were clear, and I explained how I was personally working on figuring out our hardest problems. They stopped me right there. 6/18
“Your job is not to solve the problems, your job is to tell everyone **what the problems are** so they can solve them.” 7/18
Mega confusing. This scared the shit out of me. It ran against 15 years of straight-A student habits. I obviously wasn’t writing code any more, but problem solving is what I was good at. And now I was supposed to just… state the problems so others can solve them? 8/18
(Yes. And spend time explaining _why_ these are the important problems to solve. A point our eventual People leader @AdrianaMRoche could never make too often.) 9/18
I felt horrible “dumping my problems” on the team, but at the next all hands I dutifully tried… I explained the problems we faced as a company—and strangely—the team got excited. This was weird as hell to me, but if I loved solving problems... why wouldn't everyone else? 10/18
Then @ivolo read The Everything Store by @BradStone and the Elon bio by @ashleevance. Elon and Bezos always made a point of asking the impossible of their teams. And while tough, these were actually the experiences people remembered most fondly! 11/18
I guiltily went to @christochild @vinceprignano & @stevenmiller888 and explained that Segment's fate hung on them being able to fix pricing ASAP. Realistically it should take months, but due to my failure to create clarity before, we didn’t have that time any more. 12/18
I felt awful. 13/18
But apparently I shouldn't have. Yesterday @stevenmiller888 told me: "I loved working all day all night to ship it." They shipped completely new pricing in just 5 days. It was the turning point. 14/18
With pricing fixed and soon a whipped-into-shape mobile product, we stood a fighting chance. 15/18
The sales team got their mojo back. They simply wouldn't give up. Deal after deal. And at 11:50pm on the last day of the year, we crossed $20m ARR. The team exploded. In 6 months we had reaccelerated 2.5x to 100% yoy. It was quite the party that night. 16/18
I learned my lesson: a leader’s job is first and foremost to create clarity on the problems to be solved. 17/18
(Note: this does not mean asking people to work insane hours all the time. In fact, that might be a sign clarity was created too late or not at all.) 18/18
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Scott Kupor @ScottKupor
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Jan 25, 2022
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