Starting Over in Law: How Dana McKenna Built a Modern GC Career

In this episode of This Legal Life, Ben Chiriboga sits down with Dana McKenna to unpack how a collapsing startup led her to rebuild her legal career from the ground up.

Dana openly discusses juggling uncertainty, discovering fractional GC work, and confronting internal barriers like imposter syndrome and people-pleasing. She highlights why today’s companies need strategic legal partners who can manage risk, lead proactively, and simplify complexity. An inspiring conversation for lawyers designing a career that fits their strengths—and their life.

About Our Guest:

Dana McKenna is the Founder of Align General Counsel, a fractional GC practice built on one core belief: high-growth companies deserve legal leadership that operates in true alignment with how their business actually runs.

With more than 18 years of legal experience, Dana began her career in BigLaw litigation before moving in-house, where she spent over a decade advising Fortune 5 corporations, mid-sized businesses, and scaling startups. She has served as General Counsel, Chief Legal and People Officer, and trusted advisor to founders, boards, and executive teams—bringing a rare blend of legal strategy, operational insight, and business pragmatism.

Dana’s background spans tech, staffing, marketplaces, retail, and consumer brands. She specializes in employment law, California and multi-state compliance, commercial contracting, and litigation strategy. Over her career, she has led organizations through complex restructures, PAGA litigation, high-stakes internal investigations, M&A activity, and evolving regulatory environments.

Known for her practical and people-centered approach, Dana focuses on the intersection of legal, HR, and company culture. She partners closely with leadership to deliver guidance that is clear, candid, and designed to keep the business moving forward—without slowing growth or creating unnecessary friction.

Connect with Dana:

Website: https://www.aligngeneralcounsel.com/

LinkedIn: https://www.linkedin.com/in/danabethmckenna/