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