In this episode of This Legal Life, Ben Chiriboga sits down with Joe Green, Chief Innovation Officer at Gunderson Dettmer, to explore how law firms are evolving — and what it takes to lead that change from the inside. Joe traces his journey from practicing corporate law through legal tech experimentation and his time at Practical Law at Thomson Reuters. He shares how stepping outside the traditional partner track allowed him to develop the skills and confidence needed to return to Gunderson and help shape a future-ready firm. The conversation offers timely insight for law firm leaders thinking seriously about innovation, talent, and long-term strategy.

About Our Guest:

Joe Green is the Chief Innovation Officer of Gunderson Dettmer. In this role, he leads Gunderson’s innovation strategy to transform the firm's service delivery platform and business model, with a focus on providing a more modern experience for clients, lawyers and business professionals. He was recognized by Lawdragon as one of the 100 leading AI and legaltech advisors.

Joe is a Lecturer in Law at Penn Carey Law, where he teaches a course on startups and venture capital. He has authored dozens of articles on startup-related issues, the business of law, legal technology and the future of the legal industry. He speaks regularly on these topics at industry and academic conferences, law firms and law schools, and his academic work has been cited by SEC commissioners and staff in public speeches and reports.

Joe was previously a senior associate at Gunderson and left to join Thomson Reuters as a Senior Legal Editor at Practical Law, the premier online legal know-how service for business lawyers. Joe began his legal career as a securities lawyer with Simpson Thacher in New York.

Connect with Joe:

LinkedIn: https://www.linkedin.com/in/joegreen1/

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/

In this episode of This Legal Life, Ben Chiriboga sits down with Anusia Gillespie, legal tech executive and author of Soul Toll, to explore the inner work behind career reinvention. Anusia shares how meditation, misalignment, and seven roles in ten years shaped her understanding of the “soul toll” we pay in our professional lives. She explains why trusting yourself matters more than mentors when your path is still unpaved, and how her debut novel blends leadership lessons with fantasy storytelling. A thoughtful, powerful conversation for legal professionals navigating change, ambition, and authenticity.

About Our Guest:

Anusia Gillespie is a lawyer turned novelist and RYT 200 certified yoga instructor whose debut contemporary fantasy, Soul Toll, blends corporate ambition with personal awakening. Her writing is shaped by a career at global law firms, legal tech companies, and Harvard Law School Executive Education, offering a sharp, insider perspective on high performance culture and the personal cost of chasing success.

Well known in the legal industry for her insight on leadership and transformation, Anusia now channels those themes into fiction that invites readers to question the lives they have been told to want. In Soul Toll, a high achieving attorney’s search for clarity pulls her into a hidden world, and a battle for something far more meaningful than success.

Anusia holds a JD and MBA from Boston College and a BS in Management from Tulane University. She lives north of Boston with her husband, young son, and old dog.

https://www.amazon.com/Soul-Toll-Anusia Gillespie/dp/B0FN9PSS2N/ref=tmm_pap_swatch_0

www.anusiagillespie.com

https://www.instagram.com/anusiagillespie/

https://www.linkedin.com/in/anusiagillespie/