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In-House Outliers: The Legal Operations Podcast

If you’re in legal operations, you’re an outlier. If you’re using legal tech, you’re an outlier.

In-House Outliers shares the stories and secrets of those challenging conventional wisdom of how corporate legal departments should operate. Join Brightflag co-founder Alex Kelly each week as he amplifies the voices of these enthusiasts and visionaries.


Listen on: Spotify | Apple Podcasts | Google Podcasts

Latest Episode

#27: Jameson Monteiro

In this episode, Alex sits down with Jameson Monteiro, Head of Legal Operations at Assurant. Like most guests, Jameson didn’t have a linear path into legal operations. Jameson shares his remarkable story in which he started his career as an entrepreneur of an automobile export company. With determination and perseverance, that journey led him to a temp role at Assurant, and then ultimately, he was able to advance his way up to Head of Legal Operations.

In this episode, Jameson discusses the importance of building relationships and trust with your CLO, the most impactful thing in his career, and how he was able to find his career calling in #legalops.

More Episodes

#26: Florence Chan

In this episode, Alex sits down with Florence Chan, who runs legal operations at Cloudflare. Florence started her career in big law as a Litigation Paralegal, but when she was presented with an opportunity as a Legal Operations Manager at Benefits Cosmetics, her journey turned in a new direction.

#25: Tiffany Brown

In this episode, Alex sits down with Tiffany Brown, an experienced legal operations leader. Tiffany started her career as a paralegal, but quickly her fascination and curiosity led her to a career in legal operations. In this episode, Tiffany shares her thoughts on networking, the necessity of “turning off” on a global team, and the lasting impact of the pandemic on the adoption of legal operations.

#24: Aline Bosteels

In this episode, Alex interviews Aline Bosteels, former Global Category Director Legal Services & Insurances at Philips. You’ll learn how Aline’s career evolved from entrepreneur to procurement manager, why lifelong learning is an addiction of hers, and the most important skill sets to be successful in a #legalops role.

#23: Sean Houston

In this episode, Alex interviews Sean Houston, Legal Operations Leader at The HEINEKEN Company. You’ll learn how Sean turned from sports broadcaster to legal operations leader, the most critical skillsets in his position, and why he feels it’s so important to create a tech roadmap at the start of a #legalops role.

#22: Liz Rancourt-Smith

In this episode, Alex interviews Liz Rancourt-Smith, Legal Operations Manager at Tilson Technology Management. Liz discusses early career lessons, the importance of making mistakes, and why she believes a non-traditional background has been her greatest asset.

#21: Jamie Ingles

In this episode, Alex interviews Jamie Ingles, Legal Operations Lead at Stripe. Jamie discusses why she joined Stripe’s legal team, the most critical skill sets in a legal ops role, and how prioritization is critical to her team’s success.

#20: Bill Novomisle

In this episode, Alex interviews Bill Novomisle, Director of Legal Operations at Cresco Labs. Bill discusses the path that led him to legal operations, his core areas of focus at Cresco Labs and the best pieces of advice he has received in his career.

#19: Zoe Baynes-Davidge

In this episode, Alex interviews Zoe Baynes-Davidge, Legal Operations Analyst at Ocado. Zoe discusses what attracted her to work at Ocado, why active listening is so important in her role and why she believes legal ops isn’t just a role for lawyers.

#18: Mateo Sanchez

In this episode, Alex interviews Mateo Sanchez, Head of Legal Operations at Outside. Mateo discusses the highs and lows of his career, the importance of aligning with your Chief Legal Officer and why he joined Outside’s legal team.

#17: Ashley Adams

In this episode, Alex interviews Ashley Adams, Director of Legal Operations at Contentful. Ashley discusses the path that led her into legal operations, why positivity is one of her guiding principles of leadership and the importance of mentors in her career.

#16: Colin McCarthy

In this episode, Alex interviews Colin McCarthy, CEO and Founder of Legal Operators. Colin discusses his journey into legal operations, why he created Legal Operators, and how to include diversity as a pillar within your legal ops function.

#15: Zachary Rosenblatt

In this episode, Alex interviews Zachary Rosenblatt, Legal Operations Senior Manager at The Kraft Heinz Company. Zachary discusses the career trajectory that led him into legal ops, the core areas of focus in his legal ops role, and the most impactful D&I projects he’s worked on.

#14: Morgan Smith

In this episode, Alex interviews Morgan Smith, Legal Operations Analyst at MongoDB. Morgan discusses her career journey in legal ops, her beliefs on the future of remote work in legal, and a simple trick to build your network with ease.

#13: Max Wang

In this episode, Alex interviews Max Wang, Head of Legal Operations at Waymo. Max discusses lessons learned early in his career, his approach when working with stakeholders and the core responsibilities in a legal ops role.

#12: Stephanie Hamon

In this episode, Alex interviews Stephanie Hamon, Head of Legal Operations at Norton Rose Fulbright. Stephanie discusses her journey into legal ops, her approach to change management, and how she creates a legal ops strategy.

#11: Jennifer McCarron

In this episode, Alex interviews Jennifer McCarron, Director of Legal Operations and Technology at Netflix. Jennifer discusses her philosophy of success, responses to failure, and the importance of putting the work into working relationships.

#10: Dr. Sinead Kane

In this episode, Alex interviews Dr. Sinead Kane, International Keynote Speaker on the topics of disability, law and policy. Dr. Sinead Kane shares her remarkable story into a career in law, the challenges that she faced, and what her internal motivators are that drive her to pursue her goals.

#9: Brenda Hansen and Liz Lugones

In this week’s episode, Alex interviews Brenda Hansen and Liz Lugones from UpLevel Ops. Brenda and Liz both share how they got started in their legal operations journey. They also share the importance of mentorship in their careers, and what it takes for legal operations professionals to be successful in 2022.

#8: Michael Dineen

In today’s episode, Alex interviews Mike Dineen, Director of Data Science at Brightflag about his unconventional path into #AI. In this episode Mike shares how his perspective on the legal industry before joining Brightflag and what interested him to work in this field. He also shares the impact that #AI is going to have on the next generation of lawyers and the 3 key pillars that he used to build out the data science function at Brightflag.

#7: Sheila Dusseau

In this week’s episode, Alex interviews Sheila Dusseau, Head of Global Legal Operations at Ferring Pharmaceuticals. Sheila discusses how she got into legal operations and how her experience in finance has been critical to the success in her career. She also discusses why it’s important to make mistakes and how saying “I don’t know” has been a powerful piece of advice she has received in her career.

#6: Don Keller

In this episode, Alex interviews Don Keller, Founder of Joinder. Don shares the reasons he became a lawyer, the benefits Joinder has provided to legal teams, and some of Joinder’s key accomplishments so far.

#5: Mary O’Carroll

In this episode, Alex interviews Mary O’Carroll, Chief Community Officer at Ironclad. Mary needs no introduction, as she is a powerhouse in the legal operations industry. Mary talks about her career path and her advice for legal operations professionals to grow within the industry. She also speaks to what has driven the massive growth of legal operations today.

#4: Aine Lyons

In this episode, Alex interviews Aine Lyons, VP and Deputy General Counsel, Global Legal Operations at VMware. Aine talks about how she found her calling in legal ops and the biggest lessons she learned throughout her career. She also shares the qualities that she thinks make a great legal ops professional.

#3: Mike Naughton

In episode three, Alex interviews Mike Naughton, Vice President of Marketing at xMentium and a pioneer in the legal ops industry. Mike shares his path, discussing his early learnings with working with lawyers and the DNA that makes a forward thinking general counsel. He also discusses how to use other industries as inspiration to solve the major problems that legal ops professionals face today.

#2: Tim Casey

In episode two, Alex interviews Tim Casey, General Counsel and Chief Compliance Officer of Numotion. Tim discusses his journey, sharing why he waited to go to law school and how self reflection and learning has been a tool that has helped him to build his career path in law.

#1: Stephanie Corey

In this first episode, Alex interviews Stephanie Corey, Co founder of Uplevel Ops and CLOC. You’ll learn from Stephanie about her successes and lessons learned in legal operations and what she thinks are the most important qualities to building a successful career in legal ops.