What It Takes to Keep Up With AI - Inside Docusign's Reinvention | Larry Jin, Docusign

What does it actually take to keep up with AI - not the keynote hype, but the real, ground-level version?To open Season 2 of The AI Floor, Shamil Malachiyev sits down with Larry Jin, VP of Product at Docusign, for an honest look at how one of the world's most trusted software brands is reinventing itself around AI and AI agents - and the thinking that makes a shift like that possible in the first place.Before Docusign, Larry helped build the early Microsoft Teams and worked on Amazon Alexa - close to 15 years turning hard technology into products people actually trust. In this conversation he breaks down how change really happens inside a large company: how new tools earn trust, why most AI rollouts stall, and what separates the teams keeping pace from the ones quietly falling behind.Expect to learn:• The simple value-effort-risk equation that decides whether any AI tool gets adopted• Why "just throw it into an LLM" can cost 1,000x more than it should - and the smarter way• How AI quietly became good enough to read and reason over the world's most complex contracts• Why AI agents are succeeding where rigid, 18-month software projects failed• When a workflow should stay 95% predictable - and where the 5% of "magic" belongs• Why even the biggest names in AI feel like they're behind• The two speeds of AI adoption - and where the real world actually sits today• What it takes for any team, in any industry, to keep pace with the rate of changeIf you're trying to bring AI into your own company - or just trying to think clearly about where this is all heading - this one's a blueprint.CHAPTERS 0:00 Promo1:50 Episode Open & Guest Intro2:35 Larry's path: Microsoft Teams, Alexa, DocuSign5:53 Everyone is becoming a product manager8:11 How companies actually build trust in AI13:45 The pivot: from e-signature to AI platform19:35 The Alexa lesson: the tech finally caught up21:05 Why asking ChatGPT about contracts costs $20022:31 Inside Iris & Intelligent Agreement Management28:24 The legal tech boom: Harvey & Legora partnerships36:02 One platform for sales, procurement, HR & partners43:18 DocuSign Agents: from chatbots to real actions48:41 AI agents vs 18-month CLM projects55:23 The adoption curve: everyone feels behind57:37 The 120mph innovation bubble vs the real world59:56 What's next for DocuSign – and for the rest of us👇 CONNECT WITH LARRY JINLarry Jin ► https://www.linkedin.com/in/elj4y/Docusign ► https://www.docusign.com/👇 CONNECT WITH SHAMILShamil Malachiyev ► http://www.linkedin.com/in/shamilmalachiyevFluidLabs ► https://fluidlabs.com/🔔 SUBSCRIBE for more unfiltered, ground-level conversations with the people building AI inside the world's biggest companies.ABOUT THIS CHANNELThe AI Floor (The Founder's Code, Season 2) - honest, ground-level conversations with the people actually building AI inside the world's biggest companies. No hype, just what's real.#DocusignIAM #AIAgents #EnterpriseAI #AI #TheAIFloor #LarryJin #ContractAI #ProductManagement #Podcast