Claim OwnershipFireside Chats with Tom Dreyfus and Sam Flynn
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Co-founders Tom Dreyfus and Sam Flynn bring together leaders in legaltech to discuss applications of the technology, how to approach and implement digital tools, and insights on trends in both no-code platforms and generative AI.
24 Episodes
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Securing top healthcare talent is trickier than ever.For Advocare (one of the largest independent multi-specialty physician groups in the US), that means getting physicians and other healthcare professionals signing on the dotted line…fast. Automating their contracts is one way they’re tackling this head-on. But it’s not another just a workflow tweak. It’s a necessity.In this fireside chat, Josef Co-Founder and COO, Sam Flynn, sits down with Advocare’s Vice President of Risk Management, Quality and Patient Safety, Jeremy Freshcorn.Together, they talk about Jeremy’s career in healthcare, how Advocare is putting self-service contract tools to work on Josef, the future of onboarding, and how to move to quickly and safely in highly regulated environments.
In their final Fireside Chat of the year, Co-founders Tom Dreyfus and Sam Flynn pull back the curtain on 2025.Together, they reflect on how Josef fared, the customer tools and features they loved most, the legaltech events that really stuck out, and what’s on their wish list heading into the new year.“I’ve never felt clearer on what Josef is and the problem we solve than I do today,” Sam says.Learn moreRead our recap on the Josef blogFollow Tom on LinkedInFollow Sam on LinkedIn Subscribe to their monthly newsletter
In his latest fireside chat, Josef Co-founder & CEO Tom Dreyfus sits down with Adam Fitzhenry, General Manager, People Services and Enablement at the Australian Retirement Trust (ART).As Australia’s second largest superannuation fund, ART is no stranger to operating at scale. The fund manages $330 billion for its more than 2.4 million members.Inside the business, its 3.2k employees would flock to Adam’s People team with question after question, but more often than not, the questions would be the same.The People team needed a safe, reliable way to answer these questions at scale. That way, the business could get the information it needs fast, and Adam’s team would be free to focus on the strategic, higher level work only they can do.Learn moreRead our recap on the Josef blogFollow Tom on LinkedInFollow Adam on LinkedIn
In his latest fireside chat, Josef Co-founder & COO Sam Flynn sits down with the team at Legal Aid of North Carolina. He chats with Chief Innovation Officer, Scheree Gilchrist, Innovation Lab Program Manager & Staff Attorney, Megan Hennings, and Chief Communications Officer, Helen Headrick.Together, they talk Sam through the organization’s new Josef document and guidance tools designed to help clients with all things housing. The trio give some background into how they approach innovation for sustainable, long-term impact, why confidence always beats perfection when you’re building self-service tools, and more.
In his latest fireside chat, Josef Co-founder & COO Sam Flynn sits down with Whitney Stefko Dover, Director and Senior Counsel, Policy and LegalOps+ at Ford Motor Company.From hiring the best talent, to breaking free of fixed mindsets, to creating your own “genius zone,” Whitney shares practical tips for lawyers and legal ops teams navigating legal AI today.
In his latest fireside chat, Josef Co-founder & COO Sam Flynn sits down with Dr. Hemma R Lomax, Deputy General Counsel and VP, Global Head of Ethics and Compliance at DocuSign. Together, the pair dive into Hemma’s journey from SEC enforcement to reimagining compliance functions at the likes of Disney, Snapchat, and Zendesk.Hemma explains why she sees compliance as an enabler, not a blocker, shifting from the “Office of No” to the “Office of Unlock,” the value of compliance teams as guides, how AI can help “unleash human potential,” and more.
Wendy Chow is General Counsel at Cityblock Health, a healthcare provider headquartered in New York City. Recently, her team began creating AI Q&A tools on Josef to automate repetitive Q&A, and give the business instant access to legal knowledge as and when it’s needed.Wendy sat down with Josef Co-founder Sam Flynn to talk about the tools, why successful tech adoption starts at hiring, her pragmatic take on AI, and more.
In the latest episode of Josef's Fireside Chat series, Co-founder & COO Sam Flynn sits down with LawTrades' Chief Strategy Officer and Cedar’s former Head of Legal Operations Tommie Tavares-Ferreira.The pair discuss Tommie’s journey from HBO to later becoming a leading figure within the in-house legal operations community. They unpack storytelling and its role in legal transformation, the hidden value of contracts, plus, what questions not enough of us are asking when it comes to legal AI.
Dr. Megan Ma is Executive Founding Director of liftlab at Stanford Law School.In our latest fireside chat, Josef Co-founder and COO Sam Flynn sits down with Megan to unpack how legal teams can move from passive tech adopters to active designers of their future workflows.Drawing on her background working with the Canadian government on self-driving car regulation, Megan offers a compelling analogy for how we should think about AI in legal practice. Her thesis? The art lies in how and when we invite humans into the loop.
Elaine Darr is SVP, Global Head of Digital Legal and Innovation at DHL.With a background in commercial law and over a decade in leadership, she’s redefined what’s possible both in and out of Legal. In 2024, she was named Corporate Counsel Best Deputy or Associate GC by the American Lawyer Industry Awards.Elaine knows what it takes to really innovate: structured change, business alignment, and a deep understanding of the people you want to bring along for the journey.In the days leading up DHL’s first ever Legal Innovation Summit, Josef Co-founder & COO Sam Flynn sits down with Elaine to learn about her career, DHL’s tried and true innovation playbook, her approach to legal AI, and how she believes legal teams can lead from the front.
What if contracting was easy end-to-end, and legal had more time for the more unique, trickier tasks? That’s what Sara Rayment and Andrew Medlicott have focused on at INKD, a tech-led law firm, and Inkling Legal Design, its design-first sister company.Using Josef, they’ve built self-service, AI contracting tools that help businesses draft, negotiate, send and sign contracts all without the usual, time-consuming back and forths. The tools are already in use with clients like the healthcare provider Grampians Health, earning Inking Legal Design a finalist spot in the 2025 Financial Times Most Innovative Lawyer Awards. We’re so proud!Josef Co-founder and CEO Tom Dreyfus sat down with the team to learn more about the tools, their thinking behind them, and what they see for the future of legal work.
Polaris Lawyers is a boutique personal injury law firm based in Melbourne, Australia. The firm’s no stranger to creating self-service legal tools, and in the past six months launched two, public-facing AI guidance solutions: WorkMate, which helps people navigate workers’ compensation, and The TAC FAQ tool, which answers legal questions surrounding traffic accidents.Recently, Founder and Principal Nick Mann sat down with Josef Co-founder & CEO Tom Dreyfus to chat about the tools, what the firm’s learned creating them on Josef’s AI module Josef Q, and what impact they’ve had on clients and the team at large.
Gippsland Community Legal Service (GCLS) is a legal aid organization based in Australia that provides legal services on issues ranging from family violence intervention to tenancy and housing. Recently, Principal Lawyer Simon Suttie sat down with Josef’s CEO and Co-founder, Tom Dreyfus, to dive into the organization’s work and how the team is clearing bottlenecks for its rental stress program with two self-service intake tools on Josef.
Sateesh Nori is a lawyer, author and Adjunct Professor at NYU School of Law. With over 20 years of experience in tenancy law, Sateesh has represented 1000s of low-income tenants, advocating for housing justice with organizations like The Legal Aid Society of NYC and Bedford Stuyvesant Community Legal Services.Sateesh is a techno-optimist. While some remain apprehensive about the future post-GenAI, he’s all in, researching how we can use the technology to “boost the way we help people and do more with less.”In this fireside chat, Josef Co-founder and COO Sam Flynn catches up with Sateesh to learn about his legal background and how he thinks GenAI will revolutionize the delivery of legal aid.
Thanks to their self-service tools, the global insurance company now has instant access to hyper-accurate answers on policies, playbooks, and contract guidance, all in just a few clicks.Led by Head of Legal Operations Claire Nuske, under the award-winning General Counsel Maria Marinelli, Bupa’s legal team is among the first in APAC to develop GenAI tools that increase access to legal and compliance knowledge company-wide.The new tools join Bupa’s 40+ document and workflow tools that the business has launched since first logging on to Josef back in 2022.In this fireside chat, Josef Co-founder and CEO Tom Dreyfus chats with Claire to discuss the new Josef Q tools springing up across Legal, People, Marketing and Workplace Relations. How are they changing the way the business works? What lessons have they picked up while implementing GenAI? Where to next?
Meet Thomas Stone, Senior Legal Technologist at the award-winning UK law firm TLT.Last month, Tom’s FutureLaw team won Legal Technology Team of the Year at the Legal Business Awards 2024. What for, you ask? A cutting-edge employee training solution built alongside telco giant Vodafone, all on Josef!TLT is one of the most decorated law firms in the UK, having won Law Firm of the Year three times in a row, and is internationally renowned for its expertise in financial services, clean energy, retail, and technology.You can think of Tom’s FutureLaw team as the firm’s technology arm, developing innovative legal solutions for the firm and its clients, and, in Tom’s words, “cutting through the hype to find legaltech that really adds value.”In this fireside chat, hosted by Co-founder and COO Sam Flynn, Tom explains how more lawyers are looking to create digital solutions than ever before. He shares how in-house lawyers are fast becoming data-driven juggernauts, and, amongst a whole lot else, why TLT automates on Josef.
If you don’t know Alex Herrity, adidas’ legalops superstar and Director of Legal Solutions, now’s your chance. When he’s not sharing the stage with Josef Co-founder and COO Sam Flynn in London, Alex is busy making sure adidas leverages its world-class legal team with the best technology around. He’s content so long as “every week or two, we’re getting better and more focused and delivering better things in Legal.”In a recent fireside chat, Alex and Sam caught up to discuss the current state of legal operations, the future of knowledge management, and get his take on the biggest question in legal GenAI today: build or buy?
Meet Nicola Packer, General Counsel at Fnatic, the most successful esports brand in history. Nicola’s in-house team has truly walked the walk when it comes to legal automation and AI.Fnatic first used Josef to automate dozens of contracts and agreements, ultimately saving the team one day a week. Then, in early 2023, they adopted Josef Q, going on to achieve what many businesses are still exploring today: identifying problems that GenAI can solve; managing the workflow changes that come with introducing new tools, integrating AI into Fnatic’s existing tech stack, and more.They’ve gone the whole nine yards! In conversation with Josef Co-founder and COO Sam Flynn, Nicola shares how her team has navigated all of the above and more.
Meet Bumble's Global Head of Privacy, Teodora Pimpireva Tapping. In conversation with Josef Co-founder and COO, Sam Flynn, Teodora shares the global dating app’s trick for keeping up with an ever-changing set of privacy obligations. Spoiler: it involves innovating with Josef!What role can GenAI play in the privacy space? What are Teodora’s top tips for other in-house teams looking to build new, innovative solutionsPrivacy at Bumble is now a “cool” and “beautiful” experience thanks to the team’s suite of compliance tools on Josef.
Easy governance, a simple setup, and Josef Q’s legal-centric features sit at the top of the list for the AAA team. In this fireside chat, the merican Arbitration Association President and CEO Bridget McCormack and Chief Innovation Officer Diana Didia sit down with Josef Co-founder and COO Sam Flynn.Together, the trio discuss a recent GenAI bakeoff at the AAA where the organization pitted an internally built GenAI-powered tool against one built on Josef Q. Listen to Bridget and Diana explain why they chose Josef Q, discover how the AAA believes GenAI will revolutionize access to justice, and listen for the two leaders’ tips for implementing the technology at scale.
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