The Smart Start to Legal AI: Inside Enstar’s Legal Ops Revolution with Peter Calleo and Nick Giuliano
Release Date: 10/24/2025
AI Adoption That Actually Works: How Hanna House Went from Pilot to Playbook
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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, Director, Research & Evaluation, Hanna Center, and Marissa La Brecque, VP of Research and Training, from Hanna Center, to talk about how their grassroots AI pilot turned into a full 2026 roadmap. Hear how they’re using GenAI to streamline operations, spark new ideas, and even open the door to a broader range of grant opportunities, without losing sight of their mission. Highlights ...
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The Smart Start to Legal AI: Inside Enstar’s Legal Ops Revolution with Peter Calleo and Nick Giuliano
UpLevel View
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...
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From Firefights to Fixed Fees: Strategic Pricing in High-Stakes Legal Work with Katie Armistead
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Litigation: the last stronghold of hourly billing. On the UpLevel View, Steph Corey and Ken Callander talk with Grubhub’s Katie Armistead about how legal teams are bringing order to the chaos with phase-based fees, risk-sharing, and value-driven pricing. The era of “We’ll see what the invoice says” is over. Take your Legal Leadership Vision to the Next Level: Subscribe to the UpLevel View today. Guest Additional Info Our guest today is Katie Armistead, Head of Legal at GrubHub. She began her career at Jones Day and holds a BA in Economics from Johns Hopkins University and a JD...
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More Than a Retainer: Value-Based Pricing for Ongoing Legal Advice with Collin Smyser
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Advice & Counsel work is due for a rethink. In this episode of the UpLevel View, Value Strategies Founder and pricing guru Ken Callander is joined by Collin Smyser, General Counsel of OptionCare, to explore how legal departments are moving beyond the billable hour with fixed monthly retainers. Discover how strategic advisory work is being redefined around accessibility, outcomes, and value, not minutes. Tune in and learn how to lead your legal department into a future where value, not hours, drives results. Subscribe to the UpLevel View and improve your legal leadership vision today!...
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Future-Proofing Legal – Aligning with Business Goals with April Miller Boise
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What does it take to future-proof legal? Intel's CLO, April Miller Boise, joins host Stephanie Corey to unpack how legal teams can drive business value, embrace AI, and rethink spending with value-based pricing. From leadership insights to flexible staffing strategies, this episode is a blueprint for modern legal transformation. Guest Additional Info April Miller Boise is Executive Vice President and Chief Legal Officer at Intel Corporation, where she leads the global legal, trade, and government affairs teams. Before joining Intel, she served as Chief Legal Officer (CLO) at Eaton...
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Leadership, Culture, and Community in Legal Ops: A Greatest Hits Episode of UpLevel View with Heather Reid
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This special episode, hosted by UpLevel Ops CMO Heather Reid, brings together powerful insights from some of Legal Ops’ most respected voices. From sticky-note strategy sessions to global legal transformation, we revisit five standout conversations that showcase how leadership, culture, and community are redefining modern legal departments. Featuring Christy Freer, Janene Asgeirsson, Audrey Taranto, Curt McDaniel, Jenn McCarron, and Mike Haven, this episode is a celebration of the people-first strategies and mindset shifts pushing Legal Ops to the Next Level. Highlights Tapping...
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The Importance of GC/Legal Ops; What’s Next for the LINK Community x L Suite with Greg Raiten and Shaun Sethna
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Legal Ops is evolving—are you ready? In the March episode of the UpLevel View Podcast, ULO CEO Stephanie Corey is joined by two standout leaders from The L Suite—Greg Raiten, Co-Founder, and Shaun Sethna, General Counsel—for an honest conversation about the evolving relationship between General Counsel and Legal Operations. Together, they explore why Legal Ops is no longer just a support function but a strategic partner in building agile, scalable legal teams. From navigating CLM implementations (spoiler: they’re never as easy as they look) to adopting AI and value-based pricing...
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Redefining Value in Legal Operations for 2025 with Maureen Harms
UpLevel View
What does value mean in legal operations, and how is it evolving in 2025? Join Stephanie Corey, Co-Founder and CEO of UpLevel Ops, Maureen Harms, VP and Associate General Counsel, Transition Management at 3M, and Ken Callander, Managing Principal of Value Strategies—now an UpLevel Ops company—for an exclusive discussion on the future of legal operations and pricing strategies. Together, UpLevel Ops and Value Strategies offer a powerhouse of expertise, presenting a united vision for delivering transformative results in legal departments. Steph, Maureen, and Ken will delve into the evolving...
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Flexible Solutions, Lasting Impact: ALSPs and the Future of Legal Operations with Monica Zent
UpLevel View
In the January episode of the UpLevel View, UpLevel CEO Stephanie Corey and Monica Zent of ZentLaw discuss the transformative role of ALSPs in legal departments. They tackle misconceptions, highlight ALSP benefits like reducing contract backlogs and fostering collaboration, and share real-world success stories. The conversation explores how ALSPs pave the way for legal tech adoption and future innovations like AI. Packed with insights, this episode is essential for legal professionals seeking Next Level, cost-effective, agile solutions to navigate today’s challenges. Guest’s Info Monica...
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2024 in Legal Ops: What We’ve Learned, What’s Next – An UpLevel Ops Roundtable
UpLevel View
On the December episode of The UpLevel View, Stephanie Corey, CEO of UpLevel Ops, is joined by Brian Hupp, Sumi Trombley, and Brandi Pack for “2024 Legal Ops: What We’ve Learned, What’s Next – An UpLevel Ops Roundtable.” Reflecting on this year’s advancements in AI, workflow automation, and value-based pricing, the panel shares bold predictions and actionable strategies to prepare for the year ahead. Don’t miss this thought-provoking discussion to inspire your 2025 Legal Ops goals! Highlights Discussion about AI trends in workflow automation. Brian on AI chatbots and...
info_outlineWhat 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
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Transitioning from Microsoft Co-Pilot to ChatGPT
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The role of AI in legal ops pre-pandemic
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Simplifying legal tasks with AI tools
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Board minutes drafting revolutionized by GPT-5
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Elements of a successful AI pilot program
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Rapidly expanding use cases for custom GPTs
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Legal tech transformation and the end of over-engineering
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The importance of generative AI governance
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Building a culture of innovation through AI adoption
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Measuring AI pilot program success with low cost, high reward
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Executive sponsorship critical to AI adoption success
Episode Resources
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UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef
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UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide
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Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/
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LINK (Legal Innovators Network): http://Linkforlegal.com
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Connect with Stephanie Corey
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GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/
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GAI Management Solutions from UpLevel Ops: https://uplevelops.com/services/gai-management/