The Smart Start to Legal AI: Inside Enstar's Legal Ops Revolution with  Peter Calleo and Nick Giuliano
UpLevel View24 Okt 2025

The Smart Start to Legal AI: Inside Enstar's Legal Ops Revolution with Peter Calleo and Nick Giuliano

What does practical AI success look like in legal terms? Peter Calleo and Nick Giuliano from Enstar Group join UpLevel Ops CEO, Stephanie Corey, and UpLevel's Director of Innovation, Brandi Pack, on the UpLevel View podcast. They'll share how UpLevel Ops and the Enstar team led a GenAI program that made Legal faster, smarter, and more connected to the business. No hype, just real-world insight. Listen to the UpLevel View and improve your legal leadership vision today!

Highlights

  • Transitioning from Microsoft Co-Pilot to ChatGPT

  • The role of AI in legal ops pre-pandemic

  • Simplifying legal tasks with AI tools

  • Board minutes drafting revolutionized by GPT-5

  • Elements of a successful AI pilot program

  • Rapidly expanding use cases for custom GPTs

  • Legal tech transformation and the end of over-engineering

  • The importance of generative AI governance

  • Building a culture of innovation through AI adoption

  • Measuring AI pilot program success with low cost, high reward

  • Executive sponsorship critical to AI adoption success

Episode Resources

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Episoder(33)

Building a Legal Function That Can Scale

Building a Legal Function That Can Scale

Summary Nikki Rahimzadeh joined Analog Devices as the legal department was working through a "big T" transformation, triggered by an acquisition that doubled the company's size overnight. She walks St...

27 Jul 32min

The Leadership Side of Legal Operations

The Leadership Side of Legal Operations

Summary Leadership looks very different when an entire profession is evolving. Oyango Snell, CEO of CLOC, joins Stephanie Corey to trace how Legal Ops has moved from fighting for recognition to owning...

7 Jul 34min

The New Economics of Legal Work

The New Economics of Legal Work

Episode Summary In this episode of The Uplevel View Podcast, Stephanie Corey and Brandi Pack sit down with Ryan Walker, CEO and co-founder of General Legal, to explore how AI is transforming the legal...

15 Apr 42min

Leading Legal in a Product-Led Company

Leading Legal in a Product-Led Company

Summary In this episode of Uplevel View, Stephanie Corey sits down with Betsy Cantrell, VP of Legal at HighLevel, to explore how legal teams must evolve in fast-moving, product-led organizations. Bets...

31 Mar 48min

The New Standard for Legal Leadership

The New Standard for Legal Leadership

Episode Summary How does Legal move from cost center to growth engine as expectations rise? Ron Bell, Chief Legal and Administrative Officer at Collective Health, joins Steph Corey to discuss the new ...

10 Feb 41min

The End of the Billable Hour: AI, Value, and the New Economics of Expertise

The End of the Billable Hour: AI, Value, and the New Economics of Expertise

Summary In the first episode of 2026 for the UpLevel View podcast, Stephanie Corey and Ken Callander sit down with Rita Gunther McGrath, Columbia Business School professor and Wall Street Journal colu...

14 Jan 42min

AI Adoption That Actually Works: How Hanna House Went from Pilot to Playbook

AI Adoption That Actually Works: How Hanna House Went from Pilot to Playbook

What happens when a nonprofit embraces AI not for the hype, but for the help? In the latest episode of the UpLevel View podcast, Brandi Pack and Ken Callander sit down with Cristal Cardenas Sanchez, D...

10 Nov 202532min

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