Ariana Huffington, Bill Gates, Ben Chestnutt, Jeff Bezos, Marc Benioff, Michael Dell, and Steve Jobs changed entire industries and, in some cases, the world. HuffPost demonstrated that a profitable news organization could thrive in a web-only world. Microsoft made personal computers accessible to everyone. Salesforce proved that software could be sold without CDs, a feat Mailchimp mirrored in email marketing. The world-changing journeys of Bezos, Dell, and Jobs are well documented.
Jeff Lawson irreversibly changed the CPaaS industry. There is a “before Twilio” landscape, full of little-known rules, clunky Word documents, and hidden costs. Then, there’s an “after Twilio,” characterized by equitable access, self-serve options, and transparent pricing—all now industry expectations. Jeff deserves the lion’s share of the credit.
Like I said while unpacking Twilio’s ZipWhip acquisition, Jeff had a zealot’s focus on the prize and a renegade’s disdain for the status quo. This combination propelled Twilio from $0 to $4 billion in revenue as a publicly traded company, placing him in rare company. Moreover, in the CPaaS space—notorious for its unwieldy operating environment, slow growth, and compressed margins—Jeff showed that high growth, high margins, and high value at scale were possible. That alone puts him in a singularly spectacular zip code.
Leadership transitions test a founder. In appointing Khozema Shipchandler as CEO, Jeff has avoided the genius with a 1,000-helpers trap. In Khozema, Twilio has found an executive leader with a love for grounded metrics, first-principles thinking, and an intuitive feel for the business. I’ve met many current and former Twilions who have been impressed by Khozema’s willingness to listen, learn, and get his hands dirty. While Jeff’s departure may have surprised some (more on that later), his replacement surprised none.
Much empty sensationalism surrounds Jeff’s decision to move on. He might speak about it now, later, or perhaps never, and that’s fine. He’s earned this right, as he has his place among tech’s transformative luminaries.
Congratulations, Jeff and Khozema. We can’t wait to see what both of you do next.