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 industry.

Ryan shares his journey from mathematics and early NLP work to building some of the first AI-powered legal tools at Casetext. The conversation dives into a persistent issue: despite massive advancements in AI, legal services remain expensive, inefficient, and largely unchanged for clients.

General Legal is tackling this problem head-on with a new model—combining AI-native workflows, embedded legal services, and flat-fee pricing. The result: faster turnaround times, lower costs, and a more integrated client experience.

The episode also explores the limitations of current AI models, the importance of human lawyers in the loop, and the emerging power of agent-based systems that can unlock insights from unstructured legal data without requiring heavy infrastructure like traditional CLMs.

Ultimately, this episode paints a compelling picture of a future where legal services are more accessible, efficient, and aligned with client needs.

Links & Resources

• General Legal - General Legal | AI native law firm for growing companies

• UpLevel Ops - Home Page

Legal AI legal tech AI in law billable hour disruption flat fee legal services contract review AI legal operations CLM alternatives legal automation AI agents legal innovation access to justice in-house counsel legal data analytics NLP law firms future of legal services

• 00:00–01:00 – Introduction to Ryan Walker and his background in AI and legal tech

• 01:00–02:30 – How Ryan entered legal tech and why the space fascinated him

• 02:30–04:20 – The persistent adoption problem in legal technology

• 04:20–06:05 – Why AI hasn't yet changed the client experience in legal services

• 06:05–07:30 – Launching General Legal and early traction (0 to 100+ clients)

• 07:30–09:00 – Embedding lawyers into client workflows (Slack, CLMs)

• 09:00–10:30 – The access-to-justice gap and unaffordable legal services

• 10:30–12:10 – The inefficiencies of the billable hour model

• 12:10–14:00 – AI limitations: high issue detection, low contextual judgment

• 14:00–16:00 – Why human lawyers are still essential in AI workflows

• 16:00–18:00 – Flat-fee model: $500 per contract and full lifecycle coverage

• 18:00–20:30 – Building client context through past contracts and interactions

• 20:30–23:30 – AI agents and the future of legal data analysis

• 23:30–26:00 – Replacing heavy CLMs with flexible AI-driven systems

• 26:00–End – The future: freeing lawyers from rote work to focus on high-value tasks

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/