The CEO who leads one handwritten note at a time

At smallest formerly a year, Twilio CEO Khozema Shipchandler's correct 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 all associate of the innovation company's 80-plus-person guidance squad onward of their annual retreat.

"After all 10, I have to obtain a 30-minute break," Shipchandler told Business Insider of the deliberately analog ritual, which is established partially in his own memories of being a additional younger employee at GE and how particular it felt to have a elder chief obtain notice of him.

"I have no idea what the words were, I can't remember, but I certainly recall how I felt whenever that happened," stated Shipchandler.

"If I can do that fair for one individual and it increases their confidence or their capability or their desire to go do a difficult thing, I think that's beautiful awesome," he said.

Shipchandler, 52, added that the notes assist another purpose: assisting him build relationships alongside group who could one day sit in Twilio's C-suite. He stated they typically contain a citation of a project or undertaking the chief is driving; item complimentary concerning their guidance style; and encouragement for what's next.

"At several item I'm going to retire, and there's a new generation of group that I desire to cognize closely and that I desire to cognize to cognize me intimately," Shipchandler said. "They are our bench."

'They're due information'

Founded in 2008, Twilio provides innovation that businesses use to engage alongside customers complete phone calls, texts, and emails. Shipchandler rose to the top job at the business in 2024 — his archetypal stint as CEO — following serving as chairman of communications and, before that, as functioning chief and as backing chief. He spent 22 years at GE previous to joining Twilio in 2018.

Shipchandler's handwritten notes recommendation a opening into his broader method to leadership. He stated he's committed to responding to employees' emails, texts, and Slack messages inside 24 to 48 hours and that he makes a habit of study gathering materials ongoing to regard participants' time. He additionally stated he aims to be a "straight shooter" fairly than a CEO who document complete difficult news alongside "corporate speak."

"My manner is to be as transparent as I perchance can be," he said. "I do that since I think everyone — whether it's an employee or an capitalist or the commission — they're due data that they can create decisions about."

The next generation of leaders

Shipchandler oversees a approximately 5,500-person workforce alongside optional in-office attendance, a stance increasingly at likelihood alongside policies at another ample employers, many of which have brought rear white-collar workers at smallest part-time.

He stated Twilio's remote-friendly example has held up on the metrics that matter to him: Productivity remained dependable following the business went distant during the pandemic, during recruiting, engagement, and preservation improved.

The institution has made it harder, though, to foster culture.

"We acknowledge there are downsides," stated Shipchandler, which is why he added that Twilio creates deliberate opportunities for workforce to build relationships in person. These contain periodic paid trips for squad get-togethers and liberated lunch on Thursdays at the company's San Francisco headquarters.

Shipchandler has additionally taken a contrarian perspective of center managers compared alongside several of Twilio's tech peers. Rather than reduce their ranks and have those who remain depend additional on AI, as companies including Block and Meta have done, he stated that Twilio is continuing to allocate in the midlevel cohort through training programs. Twilio's next generation of elder leaders could arrive from this group, he said, and managers bring item AI lacks.

"The item that's difficult to substitute is judgment," stated Shipchandler. "That's what the managers do."