WILMA’s Leadership Institute: Meet Ashlynn Cushing
Snapshot of this year's Leadership Institute members
WILMA’s 2026 Leadership Institute, an annual nine-month program, gives area women the opportunity to learn from leaders in the region, visit a range of local companies, and serve as each other’s personal board of directors.
WILMA’s Leadership Institute, an annual nine-month program, gives area women the opportunity to learn from leaders in the region, visit a range of local companies, and serve as each other’s personal board of directors. The program is part of the WILMA Leadership Initiative, created to empower women to lead with confidence and purpose. Meet institute member ASHLYNN CUSHING.
Ashlynn Cushing
Title: Senior Manager, Insurance Risk
Company: Live Oak Bank
How long have you been with your current employer? 10 years
Alma Mater: CFCC
Prior career experience: I joined Live Oak as a Loan Closing Specialist and transitioned into the Insurance team a few years later. I’ve spent most of my career here, building deep knowledge and stepping into increasing levels of leadership.
Current job responsibilities: I oversee the Insurance team, providing leadership, clarity, and support while ensuring our insurance processes remain accurate, compliant, and aligned with Live Oak’s standards.
Hobbies: I enjoy spending time with my family anywhere we can be together, but especially out on the water. I also love all things home design, both inside and out. When I am not working or enjoying hobbies, my Frenchie is usually finding creative new ways to get into trouble.
To learn more about WILMA’s Leadership Institute and Initiative, go to https://www.wilmamag.com/leadership/
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