Twilio CEO's annual ritual

Khozema Shipchandler handwrites personalized notes to every member of Twilio's eighty-plus-person leadership team before their annual retreat. His right hand cramps after a few hours of writing.

“After every 10, I have to take a 30-minute break.”

Rooted in his own experience

Shipchandler, fifty-two, traces the practice to his time as a junior employee at GE, when a senior leader's attention meant something to him. He cannot recall the words but remembers how it felt.

“I have no idea what the words were, I can't remember, but I definitely remember how I felt when that happened.”

Building the next generation

The notes mention a project the leader is driving, compliment their leadership style, and encourage what's next. Shipchandler says they help him build relationships with people who could one day lead Twilio.

“At some point I'm going to retire, and there's a new generation of people that I want to know intimately and that I want to know to know me intimately. They are our bench.”

Shipchandler's broader leadership style

The Twilio CEO, who became chief executive in twenty twenty-four after twenty-two years at GE, commits to responding to emails, texts, and Slack messages within twenty-four to forty-eight hours and reads meeting materials in advance.

Remote work and culture building

Shipchandler oversees roughly five thousand five hundred employees with optional in-office attendance. Productivity, recruiting, engagement, and retention improved after going remote, though he acknowledges downsides to culture building.

“We recognize there are downsides.”

Investing in middle managers

Unlike peers including Block and Meta, Twilio continues investing in midlevel managers through training programs rather than trimming ranks. Shipchandler says managers bring judgment that artificial intelligence cannot replace.

“The thing that's hard to replace is judgment. That's what the managers do.”