For Wendy Ditmore, Director of Modern Work Product GTM for the Americas at Microsoft, leadership has never been about the loudest voice in the room—it’s about making space for others to rise. Over her two-decade journey at Microsoft, Wendy has demonstrated that when technology is paired with radical empathy and intentional allyship, it becomes a powerful tool for collective empowerment.
Her journey began when a bold mentor, Sharon, recruited her into the Microsoft Learning group. Sharon’s combination of fearless leadership and compassionate coaching became a blueprint for Wendy’s own leadership ethos: lead with confidence, and lift others as you climb. “True leadership is making others feel seen, supported, and celebrated—because when one rises, we all rise,” Wendy shares. That belief has shaped every chapter of her career.
Throughout her 20 years at Microsoft, Wendy has driven transformative programs—from reimagining support services and enabling SMB field sellers to pioneering training and certification pathways for high school students and the unemployed. Yet, the common thread has always been the same: democratizing access to opportunities and ensuring those historically underrepresented in tech—women, LGBTQIA+ individuals, Black-owned businesses—are not only included but elevated.
As one of the architects behind the Black Partner Growth Initiative, Wendy helped spotlight Black-owned partners, creating new avenues for growth and visibility within Microsoft’s ecosystem. Her leadership extends far beyond corporate walls. As a mother to a transgender non-binary teen, Wendy is an unwavering advocate for LGBTQIA+ rights, using her voice and experience to build bridges of understanding. She is currently authoring a book chronicling her family’s journey, aiming to inspire and inform others navigating similar paths.
Wendy credits her success to three enduring strategies: radical empathy to understand and connect deeply with others; storytelling to illuminate what’s possible; and a commitment to learning that prioritizes listening, humility, and co-creation. She mentors women within and beyond Microsoft, guiding them to claim their space, speak with confidence, and see themselves as leaders.
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/
