Counterintuitive Lessons on How to Get Better as You Scale, From Twilio’s Jeff Lawson

Several years ago, Twilio CEO and founder Jeff Lawson unpacked his granular approach to creating company values that stick, right here on The Review. When you give it a re-read, values like “Draw the owl” and “No shenanigans” stand out as unusual choices.

That unconventional streak paired with a fresh take on oft-overlooked company building processes is something of a theme in Twilio’s story. Back in 2008, for example, Lawson received plenty of advice that developers weren't an audience, and that they should create an app instead of trying to build a business around APIs. But 13 years — and a successful IPO — later, Lawson’s seen his bet bear out.

This illustrates a classic conundrum — founders and CEOs are threading a delicate needle between approaching problems with first principles thinking and pulling from well-established playbooks. “I’m not a believer that you need to innovate all the things all the time,” says Lawson. “But if it's a process or something that you do a hundred times a day, that's a good area where you should go optimize and figure it out from first principles. Because it's a repeatable thing that your company does all day every day, and if you get better and better and better at it, you're going to build a stronger company,” says Lawson.

"As companies get bigger, the natural entropy of the universe wants to make them shittier. There's more chaos. There's more decision-making. There's more politics. But great companies use their scale to their advantage," he continues.

"That's why one principle we've started talking about quite a bit at Twilio is how we need to get better as we scale. Companies should invest energy in this idea because if you don't say it and you don’t make it a goal, chances are things will get worse.”

In this exclusive interview, Lawson reflects on the key unconventional lessons from the past 13 years of Twilio’s journey to get better with scale — including some of the company’s most critical peaks and valleys and his own evolution as CEO.

He details some initial wins, like continuing to buck trends by launching a second product in the early days of the company, but also candidly talks about the hard-won lessons, like when one of Twilio’s biggest customers significantly scaled back its investment and they had to reassess their go-to-market efforts. Lawson also shares why he took deliberate steps to get his executive team to argue more, why metrics are the least important part of annual planning, and why post-mortems should be conducted when things are running smoothly.

It’s a unique peek behind the curtain at one of the most quietly fascinating companies and CEOs around — company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats, will find heaps of inspiration to pull from his playbook.

Thanks, as always, for reading and sharing!

-The Review editors

P.S. - Prefer to listen to our interview with Lawson? Check it out here, on our In Depth podcast.

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