The CEO who leads one handwritten note at a time

Twilio CEO Khozema Shipchandler in June at the Nasdaq, celebrating the company's 10th anniversary since its IPO NYSE: TWLO Twilio CEO Khozema Shipchandler writes notes to his company's 80+ leaders before their annual retreat.

He said the analog ritual is rooted in part in his own memories of being a junior employee at GE.

The notes also help him build relationships with those who could one day sit in Twilio's C-suite, he said.

At least once a year, Twilio CEO Khozema Shipchandler's right hand cramps up from a few hours of writing.

He's not signing copies of a book.

The pain, instead, comes from penning personalized notes to every member of the technology company's 80-plus-person leadership team ahead of their annual retreat .

"After every 10, I have to take a 30-minute break," Shipchandler told Business Insider of the deliberately analog ritual, which is rooted partly in his own memories of being a more junior employee at GE and how special it felt to have a senior leader take notice of him.

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

"If I can do that just for one person and it increases their confidence or their capacity or their desire to go do a hard thing, I think that's pretty awesome," he said.

Shipchandler, 52, added that the notes serve another purpose: helping him build relationships with people who could one day sit in Twilio's C-suite.

He said they typically include a mention of a project or initiative the leader is driving; something complimentary about their leadership style; and encouragement for what's next.

"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," Shipchandler said.

"They are our bench." 'They're owed information' Founded in 2008, Twilio provides technology that businesses use to interact with customers over phone calls, texts, and emails.

Shipchandler rose to the top job at the company in 2024 — his first stint as CEO — after serving as president of communications and, before that, as operating chief and as finance chief.