Some leaders speak the loudest in a room. Others move entire organizations by seeing what no one else can—and mobilizing everyone to act on it. That is Letty Cherry in Action.
When Letty Cherry joined Microsoft 16 years ago, she didn’t know she’d be crafting narratives that would help define some of the company’s most pivotal moments—from reimagining the future of Xbox to making AI more accessible to everyone to leading global communications through a pandemic, to orchestrating Microsoft’s historic 50th anniversary celebration.
Her path into tech wasn’t traditional. With a background in psychology and public relations, Letty’s earliest roles ranged from marketing and communications in the airline industry, running Marketing and TV production for an entertainment company and helping a commercial hardware company shift to consumer software and devices. But the constant thread was always the same: curiosity, adaptability, and a gift for connecting dots others didn’t see.
Throughout her journey, Letty’s superpower remained clear: the ability to see patterns, connect people, and catalyze large-scale change.
And that’s exactly what she’s done—again and again.
That superpower—pattern recognition—became the foundation of her career. Letty made her mark early in Xbox, helping expand its narrative beyond core gamers to embrace entertainment and broader audiences. She later stepped into emerging tech domains, shaping Microsoft’s early communications in AI, Quantum, Bing, and Edge. But it was her leadership during the COVID-19 crisis that became a defining chapter.
As the world shut down, Letty stepped up. Working across 109 countries, she helped architect Microsoft’s internal and external pandemic response—from employee communications and health policies to launching vaccination clinics and delivering oxygenators to employees in need. “It was the most career-changing, awful, and inspiring experience that let me help make a difference when so many were suffering,” she recalls. “What mattered most was showing up with care and consistency.”
“The ability to recognize patterns and bring people together to act on them—that’s where real transformation begins,” – Letty Cherry.
Today, as GM of Image and Culture, Letty is a connective tissue across Microsoft’s people and storytelling systems. Her work spans global communications, social media, cultural engagement, issues management, and initiatives like the #MS50 campaign. That milestone moment, which she helped lead, was a study in orchestration—balancing pride in legacy with a vision for the next 50 years. Her contributions helped Women in Cloud to launch #empowHER50 campaign to celebrate and honor past and current women powering Microsoft’s trillion-dollar market shift.
Letty’s influence extends beyond her title. She mentors women and talent across industries, helps them find their voice, and creates pathways where others only see walls. Her strategy? Lead with trust, speak with honesty, and never hoard the knowledge.
She doesn’t just shape culture—she enables it to grow, reflect, and scale.
For Letty Cherry, transformation doesn’t begin with a podium. It begins when someone dares to ask, “How could this be better?”—and then invites others to build the answer.
About #empowHER50 campaign
This campaign celebrates women leaders at Microsoft, past and present, who have been instrumental in democratizing access to technology, opportunity, and growth. By honoring their contributions over the last half-century, this campaign highlights stories of resilience, innovation, and inclusivity. Through digital spotlights, a commemorative coffee table book, live recognition events, and more, the campaign inspires collective action toward achieving equitable societal goals. To learn more about empowHER50, please visit https://womenincloud.com/empowHER50
To learn about Microsoft 50th celebrations: https://news.microsoft.com/microsoft-50/
