General Masiello retired as a three-star general of the U. S. Air Force in 2017.
She was the Director of the Defense Contract Management Agency, where she led a team of nearly 12,000 civilians and military personnel and oversaw worldwide contracts totaling more than $2 trillion. A former assistant professor at the Air Force Institute of Technology, Gen.Masiello held a variety of systems acquisition roles during her 36-year tenure with the US Air Force, including principal contracting officer for surveillance and reconnaissance systems, weapon systems, and test ranges.
Prior to her retirement, she served as Director of the Defense Contract Management Agency and Deputy Assistant Secretary (Contracting), Office of the Assistant Secretary of the Air Force for Acquisition. She is currently President of Wendy Mas Consulting LLC and serves as a director on a variety of boards to include KBR, Inc., StandardAero, EURPAC Services, Tlingit Haida Tribal Business Corporation, and MRIGlobal. Her non-profit work includes director on the Procurement Round Table, director on the ReBuilding Together National board, and member of the Air Force Studies Board.
Key Themes Emerging from Our Conversation:
- The quiet power of women.
- It's okay to ask for something.
- The business side of service in the Air Force.
- People feed off a leader’s energy, stepping up matters.
- From teaching to buying satellites and leading aircraft teams.
- Leadership comes with moments of self-doubt and loneliness.
- As an introvert, stepping into the spotlight is a stretch.
- Leaders opened doors, often seeing potential before she did.
- It was not about being a woman; it was about being different.
- Stayed for the people, their passion, integrity, and shared sense of purpose.
- Childhood air shows and military life quietly shaped a sense of service.
- Seeking mentors vs being noticed, trusted, and given opportunities.
- One unexpected comment sparked a 36-year journey of purpose, service, and discovery.
- Facing the oath of office, the reality of what it could demand hit hard, but the instinct to protect gave conviction.
- Finding the voice others listened to and using that partnership to drive solutions.
- A learned behavior: observing what worked, adapting, and repeating until people listened.
- Leadership isn’t always loud; sometimes it’s quietly connecting with the one standing alone.
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