Sri Daita, Director of Legal Operations Technology at PayPal, joins show host CJ Saretto, Axiom's CTO, for a deep dive into how PayPal's legal ops team is accelerating driving a comprehensive AI transformation across four major workstreams: contracting, e-billing, matter management, and advice workflows.

Early successes include enabling the business to use AI-suggested contract redlines for low-risk agreements without legal touch. Attorneys can now compress weeks of regulatory analysis into minutes. Invoices can get holistic reviews across law firm, ALSP, and other provider relationships. Matters can have automated summaries, while litigation leaders can get answers to case status questions using natural language. Oh, and the legal budget and spend can be tracked in real-time. And that's just for starters.

Listen in to learn how PayPal's in-house team is getting its arms around legal AI fast, speeding deployments, generating team enthusiasm, and reaping impressive results in the process through quick wins and strategic pilot scaling.

Show Panelists

• Sri Daita is Director of Legal Operations Technology at PayPal and leads their AI transformation program, overseeing the implementation of AI-powered solutions across the company's in-house legal department.
• CJ Saretto is CTO of Axiom, and host of Axiom's Legal Tech podcast.

Key Topics

1. Why "wait a year" kills AI transformation programs before they start
2. How PayPal turbo-charged legal AI deployment
3. Why 150+ stakeholder interviews proved essential to success
4. What "without legal touch" means for business user contract redlines—and how to mitigate risk
5. When three-week-to-minutes time savings create unexpected adoption challenges
6. How manual pivot tables revealed the need for real-time AI budget tracking
7. What happens when litigation leaders query AI instead of their teams
8. How holistic invoice review catches risks individual rules miss
9. Why AI vendors rapidly upgrading their tools matters for legal buyers
10. Where the line is between AI assistance and fully automated workflows

Episode Resources

• Visit PayPal.com (https://www.paypal.com/us/home)
• Learn more about Technology & AI at Axiom (https://www.axiomlaw.com/practice-areas/technology-ai)
• Learn more about Data Privacy & Cybersecurity at Axiom (https://www.axiomlaw.com/practice-areas/data-privacy-cybersecurity)
• Learn more about Regulatory & Compliance at Axiom (https://www.axiomlaw.com/practice-areas/regulatory-compliance)
• Learn more about Legal Operations at Axiom (https://www.axiomlaw.com/practice-areas/legal-operations-support)
• Learn more about Axiom Tech+Talent (https://www.axiomlaw.com/solutions/tech-plus-talent)
• Visit AxiomLaw.com (https://www.axiomlaw.com)
• Subscribe to the Axiom Insights Podcast (https://podcasts.apple.com/us/podcast/axiom-insights-on-legal-services/id1842354058)

DISCLAIMER: Axiom is a provider of legal talent and is not a law firm, and does not provide legal advice. The information contained in these videos is merely legal information, not advice. Our clients' legal teams supervise the legal work of the Axiom lawyer. Viewing this video does not create an attorney/client relationship.

Join CJ Saretto as he corrals Peter Duffy of Titans Legal, Alex Fortescue-Webb of Legora, and Chris Frickland of Axiom for an inside look at running successful AI pilots in legal organizations. After helping Axiom test dozens of tools and compress months of contract review work into days, this group of legal AI experts unlocked the secret to achieving 10x efficiency gains that few in-house teams know.

In today's episode, learn why 14-day trials doom AI adoption before it starts, why training your AI on thousands of past contracts degrades does the exact opposite of what lawyers expect it to do (get smarter; but no, it gets dumber), and how focusing on one specific use case beats trying to solve everything at once.

The panel shares hard-won insights from their innovative structured 8-week pilot program, including why dummy data kills engagement, how vendor engagement and support makes or breaks adoption, and why it's crucial to give your lawyers 3-6 weeks to build new habits around AI tools.

Whether you're a GC evaluating generative AI tools, a legal ops leader running pilots, or a law firm partner wondering about how to measure ROI, this conversation offers field-tested strategies for what drives AI adoption in legal settings vs. expensive experimentation.

• Host: CJ Saretto, Chief Technology Officer, Axiom
• Peter Duffy, CEO and Co-founder, Titans Legal
• Alex Fortescue-Webb, Global Head of Engineering, Legora
• Chris Frickland, Director of AI, Axiom

1. Pilot Duration and Structure
2. Training and Education Approaches
3. Tool Selection Criteria
4. Use Case Identification
5. Adoption Challenges and Support
6. Future Impact on Legal Work
7. Technology Market Assessment
8. Specific Tool Implementation
9. Measuring Success and Outcomes
10. Real-World Results and Efficiency Gains
11. Organizational Rollout Strategy
12. Client Perspectives and Demands

Episode Resources

• DraftPilot's website (https://draftpilot.ai)
• Legora's website (https://legora.ai)
• Titans Legal's website (https://www.titans.legal/team)
• Learn more about Axiom Tech+Talent (https://www.axiomlaw.com/solutions/tech-plus-talent)
• Visit AxiomLaw.com (https://www.axiomlaw.com)
• Subscribe to the Axiom Insights Podcast (https://podcasts.apple.com/us/podcast/axiom-insights-on-legal-services/id1842354058)

DISCLAIMER: Axiom is a provider of legal talent and is not a law firm, and does not provide legal advice. The information contained in these videos is merely legal information, not advice. Our clients' legal teams supervise the legal work of the Axiom lawyer. Viewing this video does not create an attorney/client relationship.

Join CJ Saretto as he sits down with Daniel van Binsbergen, CEO of DraftPilot, for a candid conversation about the AI revolution in legal tech.

After running an ALSP for 10 years, applying the scientific method to contract redlining (including timing working lawyers with stopwatches), Daniel discovered the true impact today's AI has on contract work: reducing redlining from 2.5 hours to 20 minutes.

In this episode, learn why large language models (LLMs) succeeded where machine learning (ML) failed, why training on thousands of past contracts actually makes AI results worse, and how a simple "light blue highlight" became the killer feature that won over the most skeptical lawyers.

Daniel shares surprising insights from his journey from Big Law to legal AI tech entrepreneur, including why he resisted building an "apply all" recommendations button despite many requests, and how lawyers using AI well are already outpacing those who don't.

Whether you're a CLO or GC evaluating AI tools; a lawyer curious about the technology, or a legal ops professional looking to drive team efficiency, this conversation will give you practical insights on what actually works in AI-powered contract negotiation—and what's just blue-sky hype.

Show Panelists

• Host: CJ Saretto, CTO of Axiom
• Daniel van Binsbergen, CEO of DraftPilot

Key topics

1. LLMs vs machine learning in legal tech
2. The playbook revolution
3. Why historical data doesn't help
4. Building AI lawyers will actually use
5. The future of human judgment in an AI world
6. and more!

Episode Resources

• Visit DraftPilot.ai (https://draftpilot.ai)
• Learn more about Technology & AI at Axiom (https://www.axiomlaw.com/practice-areas/technology-ai)
• Learn more about Axiom Tech+Talent (https://www.axiomlaw.com/solutions/tech-plus-talent)
• Visit AxiomLaw.com (https://www.axiomlaw.com)
• Subscribe to the Axiom Insights Podcast (https://podcasts.apple.com/us/podcast/axiom-insights-on-legal-services/id1842354058)

DISCLAIMER: Axiom is a provider of legal talent and is not a law firm, and does not provide legal advice. The information contained in these videos is merely legal information, not advice. Our clients' legal teams supervise the legal work of the Axiom lawyer. Viewing this video does not create an attorney/client relationship.

Axiom's Sean Rafter connects with Hiro Oshima, Managing Director and Deputy General Counsel at SMBC, to explore the pressing challenges legal departments face as they balance pressure to adopt AI with their responsibility to manage risk.

Fresh from hosting 35 in-house counsel at an AI roundtable in New York City, Hiro discusses what true generative AI means for lawyers, why training future legal talent matters more than short-term efficiency gains, and what are the right questions to ask law firms and legal services partners about their AI use on client matters.

Today's show is packed with practical insights for legal leaders navigating AI adoption in heavily regulated industries. Hiro shares candid perspectives on measuring ROI, evaluating legal tech vendors, partnering with alternative legal service providers, and ensuring AI amplifies rather than replaces human judgment. The discussion tackles everything from law firm billing practices to law school curriculum changes in an AI-enabled world.

Show Panelists

• Host: Sean Rafter, VP and head of Axiom's financial services business
• Hiro Oshima, Managing Director and Deputy General Counsel at SMBC, overseeing approximately 50 attorneys and covering commercial banking, emerging issues including ESG, cyber, AI, and financial crime compliance. Hiro has been with SMBC for over 23 years.

Key Topics

1. Why legal departments aren't seeing AI-driven reductions in law firm billing
2. Exploring the disconnect between law firm AI adoption and client cost savings. Are efficiency gains being passed along to clients?
3. The difference between true generative AI and automation tools
4. Determining whether most legal AI applications are really using generative AI or simply extending existing automation technology with new branding
5. How to prevent AI from undermining the training of future lawyers
6. The shortsightedness of prioritizing efficiency over professional development, and how to ensure judgment and skills are gained by doing the actual work
7. When in-house teams should require client consent before their law firms use AI
8. How and why SMBC requires law firms to seek approval and validate their AI configurations, policies, and use cases before deploying AI tools on client work
9. How legal departments can measure AI ROI when there's no clear answers yet
10. Despite the lack of clear ROI metrics, legal teams can't afford to sit on the sidelines due to cost pressures and political realities
11. What makes alternative legal service providers a viable third option
12. How Axiom helps SMBC bring competent, AI-skilled lawyers in-house to hit the ground running for project-based and capacity needs without involving high costs, long pilots, or long-term hiring commitments
13. Why kindness is the most important career advice for legal leaders
14. Reflections on making tough decisions with kindness, and being mindful of lawyers' job security concerns during the GenAI revolution
15. How lawyers should view their job security in an AI-enabled future
16. Lawyers losing jobs to AI is less likely than lawyers losing opportunities to colleagues who master AI tools—and why lawyers are more necessary now than ever

Episode Resources

• SMBC Group Corporate Information (https://www.smbc.co.jp/global)
• Learn more about Axiom's Financial Services Practice (https://www.axiomlaw.com/industries/diversified-financial-services)
• Learn more about Axiom's Legal AI Solutions (https://www.axiomlaw.com/solutions/legal-technology)
• Learn more about Axiom Tech+Talent (https://www.axiomlaw.com/solutions/tech-plus-talent)
• Visit AxiomLaw.com (https://www.axiomlaw.com)
• Subscribe to the Axiom Insights Podcast (https://podcasts.apple.com/us/podcast/axiom-insights-on-legal-services/id1842354058)

DISCLAIMER: Axiom is a provider of legal talent and is not a law firm, and does not provide legal advice. The information contained in these videos is merely legal information, not advice. Our clients' legal teams supervise the legal work of the Axiom lawyer. Viewing this video does not create an attorney/client relationship.