UpLevel View

Hosted by Stephanie Corey

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Apr 2026

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About the show

Amidst the innovation renaissance in Legal Operations, it's natural to feel overwhelmed. Luckily, the UpLevel View podcast has got you covered! Join UpLevel Ops experts each month for exclusive interviews and unique insights from those who have been there and done that in Legal Ops. We'll be sharing guidance on upping your game as an effective corporate legal leader, straight talk about legal technology, and actionable ways to break out of your comfort zone and take your career to the Next Level. Don't miss a thing - subscribe to the UpLevel View podcast and improve your legal leadership vision today!

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31 recent

April 15, 2026Episode 3042 min

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 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 Keywords 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 Episode Highlights 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

March 31, 2026Episode 2948 min

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. 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. Links & Resources UpLevel Ops: http://UplevelOps.com Above The Law: http://AbovetheLaw.com Keywords 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 🎧 Episode Highlights (with timestamps) 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

February 10, 2026Episode 2841 min

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 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! Links & Resources Collective Health: collectivehealth.com Ron Bell: linkedin.com/in/ronsbell/ UpLevel Ops: http://UplevelOps.com Above The Law: http://AbovetheLaw.com Keywords 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 Episode Highlights 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

January 14, 2026Episode 2742 min

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 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

November 10, 2025Episode 2632 min

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, 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/

October 24, 2025Episode 2542 min

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 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/

September 5, 2025Episode 2430 min

From Firefights to Fixed Fees: Strategic Pricing in High-Stakes Legal Work with Katie Armistead

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/

July 21, 2025Episode 2332 min

More Than a Retainer: Value-Based Pricing for Ongoing Legal Advice with Collin Smyser

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/

June 16, 2025Episode 2244 min

Future-Proofing Legal – Aligning with Business Goals with April Miller Boise

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/

May 14, 2025Episode 2128 min

Leadership, Culture, and Community in Legal Ops: A Greatest Hits Episode of UpLevel View with Heather Reid

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/