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.

Betsy shares her journey from a highly structured corporate legal environment at Intel to building a scrappy, agile legal function from scratch in a startup. The conversation dives into how legal teams can move from being perceived as blockers to becoming strategic partners embedded within product development.

Key themes include integrating legal into product workflows, hiring adaptable talent, leveraging legal operations, and—most critically—embracing AI as a core driver of efficiency, scalability, and relevance. Betsy emphasizes that the biggest risk today isn't using AI imperfectly—it's not using it at all.

This episode is a must-listen for legal leaders looking to modernize their function, scale effectively, and stay ahead in an AI-driven world.

• UpLevel Ops: http://UplevelOps.com

• Above The Law: http://AbovetheLaw.com

Legal Operations, Product-Led Companies, In-House Counsel, AI in Legal, Legal Tech, Startup Legal, Compliance, Privacy Law, Workflow Automation, Legal Strategy, General Counsel, Legal Innovation, AI Adoption, Corporate Law, Legal Leadership

• 00:00–00:33 – Why legal involvement often comes too late in product-led companies

• 01:13–01:49 – Betsy's journey: from Intel to building a startup legal team from scratch

• 02:18–03:05 – The cultural shift: from legal authority to proving value

• 03:05–04:08 – Why legal must understand product and user experience

• 05:33–06:31 – Hiring for startups: curiosity over specialization

• 06:53–07:48 – Learning new legal domains (like privacy) on the fly

• 08:06–08:47 – Why the first hire was legal ops—not a lawyer

• 11:01–11:27 – The power of exposure and learning across domains

• 12:21–13:05 – Using competitors and AI as benchmarks for decision-making

• 15:13–16:11 – Embedding legal into product workflows without friction

• 16:55–17:34 – Using AI agents to flag legal risks automatically

• 20:29–20:45 – Why complex intake forms fail

• 21:37–22:28 – AI agents replacing repetitive legal review work

• 23:30–24:13 – The real risk: not adopting AI fast enough

• 27:01–27:43 – AI as a headcount multiplier for legal teams

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 standard for legal leadership and what it really takes for Legal to prove value, earn trust, and perform when the margin for error is small, and expectations keep going up. Listen to the UpLevel View and improve your legal leadership vision today!

• Collective Health: collectivehealth.com

• Ron Bell: linkedin.com/in/ronsbell/

• UpLevel Ops: http://UplevelOps.com

• Above The Law: http://AbovetheLaw.com

Legal leadership Cost center to growth engine Legal operations AI in legal Strategic GC Risk management Value storytelling Legal metrics Adaptability Business-first legal

Above the Law

00:00–02:15 - The rising bar for legal leadership and shrinking margin for error 02:15–03:38 - Why Legal is still treated like a cost center—and how that narrative formed 03:38–04:31 - Reframing Legal from ballast to motor 04:31–05:30 - Legal judgment vs. Legal's true job 05:30–06:39 - Outsource, automate, or stop doing the work 06:39–08:00 - Maintenance, protection, and aspirational legal work 08:00–09:31 - How experienced lawyers learn to focus on what actually matters 09:31–10:26 - AI's role in automating low-value legal work 10:26–12:23 - Why GCs get stuck in the weeds—and how to get out 12:23–13:44 - Stakeholder overload and expectation-setting 13:44–15:20 - Telling the right value story to earn respect and resources 15:20–17:02 - Being brought in early vs. "raining on the parade" 17:02–18:57 - Metrics that matter—and metrics that mislead 18:57–21:19 - Legal ops as strategic partner, not support function 21:19–25:49 - Change management and adoption challenges 25:49–31:49 - AI's impact on legal teams, hiring, and structure 31:49–34:12 - Skills future legal leaders must build 34:12–37:03 - Legal's opportunity to shape trust in unstable times 37:03–40:46 - Adaptability as the ultimate career advantage

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 columnist, to talk about how AI is forcing professional services to price outcomes instead of hours.

From law firms to in-house legal teams, the rules of value are being rewritten. The question is: who's ready to lead the change?

Listen to the UpLevel View and improve your legal leadership vision today!

Episode Highlights

00:00:18 - Introducing Rita Gunther McGrath.

00:02:23 - Definition of strategic inflection points.

00:03:21 - Legal industry disruption with AI.

00:06:47 - Shift from billable hours to value.

00:12:26 - The economic model and compensation structure challenges.

00:23:39 - Historical change movements as a model for legal transformation.

00:32:30 - Training and learning in the AI age.

00:39:36 - The concept of permissionless organizations.

00:40:15 - "Two percent less stupid" book title.

Episode resources:

• http://UpLevelOps.com

• Brainwave Newsletter by UpLevel Ops: http://UpLevelOps.com/Brainwave

• Thought Sparks Podcast: https://podcasts.apple.com/us/podcast/thought-sparks/id1546758719

• Thought Sparks Newsletter on Substack: https://thoughtsparks.substack.com

• Learn more about Professor McGrath at: http://RitaMcGrath.com

Keywords

• UpLevel View

• Stephanie Corey

• Ken Callander

• Rita Gunther McGrath

• strategy

• innovation

• Columbia Business School

• Wall Street Journal

• Thinkers 50

• The End of Competitive Advantage

• Seeing Around Corners

• AI

• inflection points

• disruption

• value-based pricing

• legal industry

• billable hours

• professional services

• general counsel

• law firms

• legal operations

• Uber

• Airbnb

• marijuana legalization

• economic model

• law firm culture

• consulting firms

• transformation

• change management

• in-house teams

• apprenticeships

• legal training

• skill development

• future partners

• media industry

• Hollywood

• entertainment industry

• strategy

• scarcity

• permissionless organizations

• two percent less stupid

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

• Streamlining data collection at Hanna Center.

• Hanna Center's mission and services overview.

• Significant data entry challenges faced early on.

• Custom AI tools drastically reduce manual data entry.

• Adoption process and early AI successes.

• Building confidence and addressing privacy concerns.

• Efficient internal adoption fuels enthusiasm.

• Insights into using AI for organizational transformation.

• Impressive ROI from AI tool implementation.

• Planning and prioritizing AI use cases for next year.

• Enhancing grant opportunities with AI tools.

• Recommended starting points for non-profits using AI.

• Creative applications of AI across departments.

• Hanna Center's evolving use of AI and future plans.

Episode Resources

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef

• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide

• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/

• LINK (Legal Innovators Network): http://Linkforlegal.com

• Connect with Stephanie Corey

• https://www.linkedin.com/in/stephcorey-ulo

• https://fr.linkedin.com/company/uplevel-ops

• https://uplevelops.com/

• https://uplevelops.com/legal-operations-consulting/

• https://uplevelops.com/thoughtleadership/

• https://uplevelops.com/services/gai-management/

• GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/

• https://www.intel.la/content/www/xl/es/homepage.html

• GAI Management Solutions from UpLevel Ops: https://uplevelops.com/services/gai-management/

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

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef

• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide

• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/

• LINK (Legal Innovators Network): http://Linkforlegal.com

• Connect with Stephanie Corey

• https://www.linkedin.com/in/stephcorey-ulo

• https://fr.linkedin.com/company/uplevel-ops

• https://uplevelops.com/

• https://uplevelops.com/legal-operations-consulting/

• https://uplevelops.com/thoughtleadership/

• https://uplevelops.com/services/gai-management/

• GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/

• https://www.intel.la/content/www/xl/es/homepage.html

• GAI Management Solutions from UpLevel Ops: https://uplevelops.com/services/gai-management/

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 from Columbia Law School.

Highlights

• Challenges of Unpredictable Litigation

• Transition from Hourly to Value-Based Pricing

• The Catalyst: A Costly Lawsuit Experience

• Success Payments and Outcome Alignment

• The Importance of Data and Piloting New Models

• Overcoming Resistance to Change

• Impact of AI on Legal Services

• The Effectiveness of Value-Based Pricing Over Hourly Models

• Improvements in Finance Team Relations and Predictability

• Advice for Legal Leaders on Pricing Strategies

Episode Resources

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef

• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide

• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/

• LINK (Legal Innovators Network): http://Linkforlegal.com

• Connect with Stephanie Corey

• https://www.linkedin.com/in/stephcorey-ulo

• https://fr.linkedin.com/company/uplevel-ops

• https://uplevelops.com/

• https://uplevelops.com/legal-operations-consulting/

• https://uplevelops.com/thoughtleadership/

• https://uplevelops.com/services/gai-management/

• GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/

• https://www.intel.la/content/www/xl/es/homepage.html

• GAI Management Solutions from UpLevel Ops: https://uplevelops.com/services/gai-management/

• April Miller Boise on LinkedIn: https://www.linkedin.com/in/april-miller-boise-8913404/

• Stephanie Corey on LinkedIn: https://www.linkedin.com/in/stephcorey-ulo/

• Ken Callander's bio: https://uplevelops.com/our_team/ken-callander/ Ken's LinkedIn profile: https://www.linkedin.com/in/kencallander/

• UpLevel Ops: http://uplevelops.com/

• Value Strategies from UpLevel Ops: https://uplevelops.com/valuestrategies/

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!

Guest Additional Info

Collin Smyser is General Counsel and Corporate Secretary at Option Care Health. Collin has decades of in-house experience, including companies such as Walgreens, Kimberly-Clark, and Elanco. At Option Care, he leads legal and governance across a nationwide healthcare provider network. Beyond the boardroom, Collin is driving industry-wide change, from policy panels to advocacy for home-based care.

Highlights

• Challenges of hourly rate pricing.

• Predictability and the burden of hourly billing.

• Perception of value in legal services.

• Importance of delivering on pricing commitments.

• Benefits of service level agreements.

• Predictability reduces internal and vendor frictions.

• Scoping advice and counsel work.

• Dealing with changes in the scope of legal work.

• Using advice and counsel work to secure bigger projects.

• Implementing change management for pricing models.

• Handling institutional knowledge in firm transitions.

• Competitive processes sharpen firm proposals.

• Starting small with value-based pricing transformations.

Episode Resources

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef

• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide

• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/

• LINK (Legal Innovators Network): http://Linkforlegal.com

• Connect with Stephanie Corey

• https://www.linkedin.com/in/stephcorey-ulo

• https://fr.linkedin.com/company/uplevel-ops

• https://uplevelops.com/

• https://uplevelops.com/legal-operations-consulting/

• https://uplevelops.com/thoughtleadership/

• https://uplevelops.com/services/gai-management/

• GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/

• https://www.intel.la/content/www/xl/es/homepage.html

• GAI Management Solutions from UpLevel Ops: https://uplevelops.com/services/gai-management/

• April Miller Boise on LinkedIn: https://www.linkedin.com/in/april-miller-boise-8913404/

• Stephanie Corey on LinkedIn: https://www.linkedin.com/in/stephcorey-ulo/

• Ken Callander's bio: https://uplevelops.com/our_team/ken-callander/ Ken's LinkedIn profile: https://www.linkedin.com/in/kencallander/

• UpLevel Ops: http://uplevelops.com/

• Value Strategies from UpLevel Ops: https://uplevelops.com/valuestrategies/

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 Corporation and Meritor Inc. Earlier in her career, she practiced on Wall Street and later led the Cleveland office of Am Law 200 firm Thompson Hine, where she also sat on the executive committee.

With a career spanning complex legal and business environments across various sectors, including semiconductors, automotive, and energy, April brings deep expertise in corporate governance, regulatory strategy, and global risk management.

Highlights

• From legal expert to strategic business partner.

• Creating alignment with company strategy.

• Strategy on a Page (SOAP) method.

• Importance of prioritization in legal work.

• Introducing SWOT Analysis.

• Stop, Start, and Continue exercise for efficiency.

• Alternatives to traditional legal staffing.

• Leveraging flexible legal talent.

• Generative AI: A paradigm shift.

• AI's potential in knowledge management.

• Training and mentoring in an AI-driven future.

• Expanding access to justice through AI.

• The evolving role of future CLOs.

Episode Resources

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef

• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide

• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/

• LINK (Legal Innovators Network): http://Linkforlegal.com

• Connect with Stephanie Corey

• https://www.linkedin.com/in/stephcorey-ulo

• https://fr.linkedin.com/company/uplevel-ops

• https://uplevelops.com/

• https://uplevelops.com/legal-operations-consulting/

• https://uplevelops.com/thoughtleadership/

• https://uplevelops.com/services/gai-management/

• GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/

• https://www.intel.la/content/www/xl/es/homepage.html

• GAI Management Solutions from UpLevel Ops: https://uplevelops.com/services/gai-management/

• April Miller Boise on LinkedIn: https://www.linkedin.com/in/april-miller-boise-8913404/

• Stephanie Corey on LinkedIn: https://www.linkedin.com/in/stephcorey-ulo/

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 hidden risks: Humanizing legal tech.

• Janene Asgeirsson on transforming skepticism to tech enthusiasm.

• Staying competitive: Embracing legal technology.

• Capturing business speed and building effective interfaces.

• Audrey Taranto's business empowerment shift.

• Generative AI and consulting roles in legal.

• From cost center to vision: Legal's evolving role.

• Curt McDaniel's scalable, smarter legal services.

• Bridging overwhelms strategic legal operations.

• Legal transformation: A journey of progress.

• Jenn McCarron and Mike Haven: Collaboration's impact on legal ops.

• Collective innovation driving the legal industry forward.

Episode Resources

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef

• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide

• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/

• LINK (Legal Innovators Network): http://Linkforlegal.com

• Connect with Stephanie Corey

• https://www.linkedin.com/in/stephcorey-ulo

• https://fr.linkedin.com/company/uplevel-ops

• https://uplevelops.com/

• https://uplevelops.com/legal-operations-consulting/

• https://uplevelops.com/thoughtleadership/

• https://uplevelops.com/services/gai-management/

• GAI Management Services from UpLevel Ops: https://uplevelops.com/services/gai-management/

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 models, this discussion gets into the real-world challenges legal departments face—and the solutions that actually work. The trio also reflects on the recent LINK + L Suite events and the magic that happens when legal leaders and ops professionals share a room (and a few hard truths). Whether you're a solo GC or leading a mature legal department, this episode is packed with insight, candor, and a healthy dose of humor. Don't miss this inspiring conversation—subscribe now and take your legal leadership to the Next Level!

Highlights

• Greg's Insight: Hiring Legal Ops as a first hire.
• Sean's View: Legal Ops importance across economic cycles.
• Greg's Observation: Lawyers don't learn operational efficiency.
• Steph on Legal Strategy: Aligning legal teams with business growth.
• Greg on Events: Successful merge of communities.
• Greg's Approach: Legal ops communities and event strategy.
• Sean's Insight: GC curiosity and legal ops evolution.
• Greg on Legal Tech: Importance of adapting to change.

Episode Resources

• UpLevel Ops Master Chef GPT: https://chatgpt.com/g/g-oVwrdPo0I-master-chef
• UpLevel Ops Wanderlust GPT: https://chatgpt.com/g/g-eDSeep6qT-wanderlust-guide
• Thought Leadership from UpLevel Ops: https://uplevelops.com/thoughtleadership/
• LINK (Legal Innovators Network): http://Linkforlegal.com
• Connect with Stephanie Corey
• https://www.linkedin.com/in/stephcorey-ulo
• https://fr.linkedin.com/company/uplevel-ops
• https://uplevelops.com/
• https://uplevelops.com/legal-operations-consulting/
• https://uplevelops.com/thoughtleadership/
• https://uplevelops.com/services/gai-management/
• The L Suite: https://www.lsuite.co/
• Shaun Sethna on LinkedIn: https://www.linkedin.com/in/shaunsethna/
• Greg Raiten on LinkedIn: https://www.linkedin.com/in/gregraiten/