Years before legal tech hit the mainstream, Jake Saper was already placing bets. As a General Partner at Emergence Capital, Jake helped fund foundational legal tech startups like Ironclad and SimpleLegal—long before most VCs would touch the sector.

In this episode, Mary sits down with Jake to unpack his early insights and where he sees the industry heading next. From CLM to AI agents, they explore what’s real, what’s hype, and what buyers and founders should really be paying attention to.

Jake isn’t just a savvy investor—he’s a pattern recognizer who sees how AI, pricing models, and workflow orchestration are reshaping not only software but the very structure of legal services.

In this episode:

• Why Legal Was an Early Bet

  Jake shares why legal’s inefficiencies and high-value work made it an obvious investment target, even before AI and legal ops were mainstream.

• The Rise (and Risk) of Legal AI

  From hallucinating tools to real-world adoption challenges, Jake and Mary dissect the current state of AI in legal—and why the billable hour is squarely in the crosshairs.

• From Tools to Outcomes

  A candid look at how law firms must overhaul their business models to align with AI-driven efficiencies—and what that means for buyers and vendors alike.

• “CLM is Dead”? Not So Fast.

  Jake unpacks why great SaaS isn’t going away anytime soon, despite the buzz around AI agents and “vibe coding.” Hint: trust, workflow, and guarantees still matter.

• How to Vet Startups in the AI Gold Rush

  In an era of fast-moving tech and 5-person billion-dollar teams, Jake outlines how to evaluate early-stage legal AI companies: speed, founder authenticity, and value creation over vanity metrics.

• A Billion-Dollar Perspective

  Emergence Capital’s latest fund doubles down on the future of B2B SaaS. Jake shares where he’s placing bets—and why job-to-be-done is still the framework that matters most.

Whether you're leading a law firm, investing in legal tech, or trying to future-proof your team, this episode is a crash course in thinking strategically about what’s next.

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