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. He spent 22 years at GE prior to joining Twilio in 2018.
Shipchandler’s handwritten notes offer a window into his broader approach to leadership. He said he’s committed to responding to employees’ emails, texts, and Slack messages within 24 to 48 hours and that he makes a habit of reading meeting materials in advance to respect participants’ time. He also said he aims to be a “straight shooter” rather than a CEO who papers over hard news with “corporate speak.”
“My style is to be as transparent as I possibly can be,” he said. “I do that because I think everyone — whether it’s an employee or an investor or the board — they’re owed information that they can make decisions about.”
The next generation of leaders
Shipchandler oversees a roughly 5,500-person workforce with optional in-office attendance, a stance increasingly at odds with policies at other large employers, many of which have brought back white-collar workers at least part-time.
He said Twilio’s remote-friendly model has held up on the metrics that matter to him: Productivity remained steady after the company went remote during the pandemic, while recruiting, engagement, and retention improved.
The arrangement has made it harder, though, to foster culture.
“We recognize there are downsides,” said Shipchandler, which is why he added that Twilio creates deliberate opportunities for employees to build relationships in person. These include periodic paid trips for team get-togethers and free lunch on Thursdays at the company’s San Francisco headquarters.
Shipchandler has also taken a contrarian view of middle managers compared with some of Twilio’s tech peers. Rather than trim their ranks and have those who remain rely more on AI, as companies including Block and Meta have done, he said that Twilio is continuing to invest in the midlevel cohort through training programs. Twilio’s next generation of senior leaders could come from this group, he said, and managers bring something AI lacks.
“The thing that’s hard to replace is judgment,” said Shipchandler. “That’s what the managers do.”
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