Megan LaBossiere

Background on Megan LaBossiere

• 2009 U.S. Naval Academy graduate
• Former H-60 Search and Rescue helicopter pilot
• MBA from Georgetown University (completed part-time while still in service)
• Over 15 years of leadership experience in and out of the Navy
• Currently a Senior Relationship Manager in Commercial Banking at Bank of America
• Formerly at JP Morgan through a veteran leadership development program

Key Themes & Insights

1. Transition Challenges & Mindset

• Transitioning out of the military can be disorienting: loss of structure, lack of career clarity, and decisions (e.g., where to live) that were previously made for you.
• LaBossiere emphasized starting early, leveraging networks, and engaging in “career exploration” well before separation.
• It’s okay to have knowledge gaps. Success comes from recognizing them and actively closing them through learning.

2. Industry vs. Function Pivot

• Function Pivot: Same industry, different role (e.g., military to defense contractor)
• Industry Pivot: Same role, different industry (e.g., military pilot to commercial pilot)
• Double Pivot: Different role and industry; The hardest path but not impossible (e.g., Navy pilot to commercial banker)

3. Path to Finance

• Chose banking for its challenges and opportunities, despite having no finance background

• Used her MBA to build business acumen and credibility

• Participated in structured programs like FourBlock and American Corporate Partners (ACP) for mentorship and exposure

4. Commercial Banking Defined

• LaBossiere works with companies between $50M and $2B in annual revenue
• Serves as a relationship manager, connecting clients to the right products and internal partners (e.g., credit, treasury, FX)
• Success relies on interpersonal skills, executive presence, and leadership; all of which veterans already possess

5. Translation of Military Experience

• Avoid military jargon in interviews and resumes; use plain language
• Always “speak for the job you want, not the job you had”
• Test your resume on someone unfamiliar with military terms to ensure clarity

6. Impostor Syndrome & Confidence

• LaBossiere discussed feeling out of place at Georgetown and JP Morgan
• Graduated in the top 20% at Georgetown despite doubts
• Encouraged listeners to not discount themselves. Many peers learn on the job too

Career Advice Nuggets

• Make finding a job your job — be deliberate and proactive
• Conduct informational interviews (coffee chats) to explore unfamiliar industries
• Use tools like a net worth tracker to assess your financial position and goals
• Read Die With Zero to reconsider retirement planning and money usage

Personal Financial Strategy

• Owns multiple homes including rental properties
• Maintains an aggressive investment strategy with diversification
• Believes in living intentionally, rather than deferring enjoyment to an uncertain future

Final Notes

• LaBossiere recently transitioned to Bank of America for increased responsibility and compensation, motivated in part by the leadership of a Black female market executive
• She emphasized the importance of representation, sponsorship (vs. mentorship), and women of color in leadership
• Expressed commitment to giving back and supporting fellow veterans in their transitions

Resources Mentioned

• FourBlock Foundation
• American Corporate Partners (ACP)
• Die With Zero by Bill Perkins
• USAA for free financial advice