Fireside 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.

  1. 12/19/2025

    Just the two of us! Co-founders Tom Dreyfus & Sam Flynn reflect on 2025 at Josef

    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 more Read our recap on the Josef blogFollow Tom on LinkedInFollow Sam on LinkedIn Subscribe to their monthly newsletter

    39 min

  2. 12/17/2025

    "We’re saving 15 minutes per question": The Australian Retirement Trust’s Adam Fitzhenry on how the People team is safely answering questions at scale with AI

    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 more Read our recap on the Josef blogFollow Tom on LinkedInFollow Adam on LinkedIn

    27 min

  3. 11/17/2025

    Legal Aid of North Carolina talk sustainable innovation, building systemic change, and automating client guidance with Josef

    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.

    35 min

  4. 10/29/2025

    What makes a great legalops hire? Ford’s Whitney Stefko Dover talks curiosity, credentials, and finding your “genius zone”

    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.

    37 min

  5. 09/11/2025

    DocuSign’s Hemma R Lomax talks AI, compliance, and creating the "Office of Unlock"

    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.

    28 min

  6. 08/19/2025

    Cityblock Health's GC Wendy Chow talks automating Q&A with Josef, AI adoption hacks, 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.

    40 min

  7. 07/07/2025

    The power of storytelling and contracts with LawTrades' Tommie Tavares-Ferreira

    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.

    42 min

  8. 06/18/2025

    When should lawyers step in? Stanford’s Dr. Megan Ma on how “useful” legal AI starts with intelligent UX

    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.

    31 min
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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.

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