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Twilio CEO Writes Personal Notes to Leaders

Khozema Shipchandler prioritizes individual connection with his staff through an annual handwritten letter tradition.

Updated on Sept. 21, 2026 in Remote Work

A close-up of blank cream-colored stationery and a sleek metal pen on a dark walnut desk, representing a professional leadership tradition.
Twilio CEO Khozema Shipchandler continues his annual tradition of writing handwritten notes to company leaders, a practice he uses to track internal talent and build individual professional connections. AI Illustration. Upload story photo >

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Twilio CEO Khozema Shipchandler maintains an annual tradition of writing handwritten notes to over 80 company leaders. The practice serves to track internal talent and encourage potential future leaders.

Why it matters

The note-writing ritual reflects Shipchandler's leadership philosophy of prioritizing individual connection and showing respect for the time and contributions of his staff. He focuses on specific initiatives and leadership strengths for every recipient.

Twilio reported $1.5 billion in revenue in Q2 2026, up from $1.41 billion in organic revenue during the first quarter. The company has set a long-term goal to grow from its current scale to a $10 billion entity.

The players

Khozema Shipchandler

He is the current CEO of Twilio who previously spent 22 years working at General Electric.

Twilio

This cloud communications platform company currently maintains an optional office attendance policy for its employees.

The details

Shipchandler, who joined Twilio in 2018 and became CEO in January 2024, replaces approximately 60% of his direct reports and 40% of vice presidents as part of his strategy. He commits to writing the notes in batches, taking mandatory 30-minute breaks after every 10 letters to manage hand cramping.

Timeline

  1. Khozema Shipchandler joined Twilio in 2018.

  2. Shipchandler became CEO in January 2024.

  3. Twilio reported $1.41 billion in organic revenue during Q1 2026.

  4. Shipchandler discussed company growth in May 2026.

  5. Twilio reported $1.5 billion in revenue during Q2 2026.

Market Landscape

This personal outreach strategy distinguishes Twilio within the tech sector where optional office attendance is the norm. It positions the company leadership as focused on talent retention and internal culture during a period of significant executive restructuring.

While the CEO's personal letter-writing habits do not directly impact daily retail pricing, the company's shift in leadership and revenue growth goals affects long-term stability for its 300,000 customers. Shareholders and observers monitor these cultural initiatives as indicators of the company's operational health.

The takeaway

Leaders can foster deep organizational loyalty by finding analog ways to acknowledge employee contributions in high-tech environments. Prioritizing direct communication can help maintain personal engagement even when staff are not in a shared physical office.

Further reading

For more on evolving corporate structures, visit the Remote Work section.

Source note: This article includes information reported by WebProNews.

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Do you believe handwritten communication improves professional relationships in a digital workplace?