Leadership1 publisher2 min readPublished
Once a year, Twilio's CEO hand-writes 80-plus notes to his succession bench
Khozema Shipchandler stops for half an hour after every 10 notes, and each one has to name what that leader is actually driving. The ritual obliges the CEO to know 80 people's work, and he calls that group Twilio's bench.
The Board Room · Leadership desk
What happened
- Twilio CEO Khozema Shipchandler writes a personalized note by hand to every member of the company's 80-plus-person leadership team before their annual retreat, and his right hand cramps after a few hours of it.
- He told Business Insider he has to stop for 30 minutes after every 10 notes, a ritual he traces partly to a senior leader at GE taking notice of him when he was junior.
- Twilio keeps putting middle managers through training programs, while Block and Meta have trimmed manager ranks and had those who remain rely more on AI.
Compiled by The Board RoomSomething wrong?How this is made
Why it matters
- cost The cost is CEO time and CEO memory: most of a working day once a year, plus knowing eighty people's projects well enough to write one specific line about each. Shipchandler has to hold that knowledge himself.
- constraint Attendance is optional, so senior contact with the bench happens only when someone schedules and funds it. Relationships an in-office company collects incidentally have to be bought here.
- decision Twilio keeps training midlevel managers while two large peers cut them. That payroll cost will have to be defended the next time margins come under question.
- exposure Calling the 80 the bench sets a standard the company can be measured against. The next C-suite opening goes to someone in that group, or Twilio has to tell the succession story differently.
Each note names a project or initiative the leader is driving, adds something complimentary about their leadership style, and closes with encouragement for what comes next [4]. Producing eighty of those requires the writer to hold current knowledge of eighty people's work. The knowledge has to be his.
The time cost is legible from his own description. Eight batches of ten, with a half-hour stop between batches, puts at least three and a half hours of pauses around the few hours of writing [1]. Twilio employs roughly 5,500 people [10], so the 80-plus leadership team is about 1.5 percent of the company, one employee in 69 [2].
Shipchandler said the notes help him build relationships with people who could one day sit in Twilio's C-suite [5]. "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," he told Business Insider [6]. Business Insider did not report how many of the 80 have since moved into bigger jobs [4].
Optional in-office attendance changes what a chief executive learns by accident. Shipchandler said productivity held steady after Twilio went remote during the pandemic while recruiting, engagement and retention improved [11], and he also said, "We recognize there are downsides," on culture [12]. The company pays for periodic team get-togethers and gives out free lunch on Thursdays at its San Francisco headquarters [13].
Two of his other habits cost far less per person. He said he answers employees' emails, texts and Slack messages within 24 to 48 hours, and that he reads meeting materials in advance to respect participants' time [7]. "My style is to be as transparent as I possibly can be," he said [8].
The middle-manager position is the second half of the same bet. Shipchandler said Twilio's next generation of senior leaders could come from the midlevel cohort the company keeps putting through training programs [15]. "The thing that's hard to replace is judgment," he said. "That's what the managers do" [16]. Block and Meta trimmed manager ranks and had those who remain lean more on AI [14].
He is the company's own example of the path. He spent 22 years at GE before joining Twilio in 2018 [18], and reached the top job in 2024 after serving as president of communications and, before that, as operating chief and finance chief [17]. Six years from joining to CEO, and it is his first time in the role [3].
What to watch
- Whether Twilio discloses how many of the 80-plus leaders move into C-suite or senior roles.
- Whether optional in-office attendance survives a quarter in which Shipchandler's retention or productivity numbers turn.
- Whether the middle-manager training spend holds through the next round of cost cutting.