Is CLM Dead? Rebuilding Legal Infrastructure in the Agentic AI Era With Simon McCarthy

How a Theatre Teacher and an Entrepreneur Built Ludus: The Software Powering Performing Arts with Zachary Collins

In this episode, Gavin Savage sits down with Zachary Collins, CEO & Co-Founder of Ludus, one of the most quietly impressive vertical SaaS companies in the US. Ludus didn’t start as a startup; it started as a favor. A college student building a small tool to help his former theatre teacher sell tickets for a school play. That “side project” would evolve into the operating system for performing-arts organizations, serving thousands of theatre programs, community venues, and arts groups across the US. Zach shares the full journey: * How a quirky, hyper-specific workflow in performing arts became a massive SaaS opportunity * The moment he realized Ludus wasn’t a side project anymore * Why vertical SaaS is in its “Netflix moment” - and how Ludus rode that wave * How the company went from bootstrapped, profitable - $1M+ revenue without outside capital * What really happened inside Ludus when COVID hit and ticket sales went to zero * The bets they made under pressure - virtual shows, streaming, distancing tools — that kept the business alive * How competitors folded while Ludus accelerated into 2021 and beyond * The distribution engines that took them to thousands of organizations and millions of seats filled * How Zach thinks about workflow depth, moats, and deciding which adjacent products to build * What finally pushed him to raise their first institutional round after a decade of bootstrapping * How he’s preserving Ludus’ culture, discipline, and customer-obsession while scaling the team * And the lessons he wants every vertical SaaS founder to hear - especially those in their own “COVID moment” This is a story about grit, timing, deep workflow empathy, and vertical SaaS. If you care about vertical software, real product-market fit, or building beloved tools in unsexy industries, this one's a must listen! ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

Building the Legal Stack: Retrieval, Context, and Real-World ROI, with Nitish Mutha, Co-founder & CTO of Genie AI

In this episode of The Vertical SaaS Podcast, Gavin Savage sits down with Nitish Mutha, Co-founder and CTO of Genie AI, to unpack how the company is building the next generation of legal infrastructure, a true agentic legal stack that combines retrieval, reasoning, and trust. Nitish shares his journey from engineer to founder, and how Genie evolved from a two-person experiment in Barclays Ventures’ Eagle Labs to one of the UK’s most ambitious AI startups. He discusses how LLMs transformed Genie’s speed of innovation, why retrieval and context are core to reliability, and how the team defines real-world ROI in a market crowded with hype. The conversation dives deep into product-led growth, defensibility in vertical AI, hiring for adaptability, and how Genie is creating the foundation for a world where AI handles not just contracts but legal reasoning itself. `TAKEAWAYS * Nitish’s engineering background shaped Genie’s product philosophy and technical depth. * Genie AI evolved from serving lawyers to empowering business users and teams. * Retrieval, context, and reliability are at the heart of Genie’s legal reasoning engine. * The rise of LLMs unlocked Genie’s product velocity and scale. * The company’s 7-year R&D head start led to a £13.3M Series A from GV and Khosla. * Product-led growth remains key to sustained adoption in legal AI. * Hiring centers on curiosity, adaptability, and ownership. * Trust, defensibility, and measurable ROI define success in legal AI. * The legal industry is shifting from manual workflows to intelligent systems. * Genie AI’s long-term vision: the core legal stack for modern businesses. CHAPTERS 00:00 – Introduction to Genie AI and Nitish’s background 02:39 – Early challenges and the first product iterations 05:24 – Shifting focus from lawyers to business users 08:20 – The impact of LLMs on product speed and accuracy 11:26 – Finding early market validation 14:02 – The funding journey: from bootstrap to GV and Khosla 17:08 – Product-led growth and differentiation in legal AI 20:08 – Driving adoption and defining ROI 22:50 – Advice for building vertical AI products 24:11 – Reliability, hallucinations, and real-world guardrails 29:07 – Ensuring quality and trust in AI systems 31:30 – Inside Genie’s technical stack: retrieval and reasoning 38:33 – Scaling post-LLM: product, team, and culture 43:26 – Hiring and leadership in an AI-first startup 46:25 – The future of agentic legal and Genie’s long-term vision KEYWORDS Genie.ai, Legal Tech, Artificial Intelligence, LLMs, Agentic AI, Contract Management, Startup Funding, Product-Led Growth, Hiring Strategies, Legal Automation, Technology Innovation ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

Wedges, Wrappers, and Alligator Blood: Nick Tippmann, Founder & GP at TipTop VC on Scaling Vertical SaaS and Spotting Real AI

In this episode of The Vertical SaaS Podcast, host Gavin Savage sits down with Nick Tippmann, Managing Director at TipTop Ventures and founding CMO of Greenlight Guru, to unpack what it really takes to scale, stand out, and survive in the world of vertical SaaS and AI. From scaling a medtech SaaS to tens of millions in ARR to backing the next generation of AI-native vertical products, Nick brings a rare blend of operator empathy and investor clarity. He shares the playbooks that still work, what founders get wrong about category creation, and why “AI wrappers” aren’t dead — they’re just the beginning. We explore: * How Greenlight Guru built a dominant founder brand in a compliance-heavy niche * Why narrow ICPs win in early-stage SaaS and how to avoid the “go broad” trap * How to use media and domain expertise to manufacture trust at scale * What it really means to create a category (and when not to) * The evolution from Vertical SaaS 1.0 to 3.0 (Workflow > Fintech > AI) * How TipTop Ventures spots real defensibility beyond LLM hype * Why culture is a second product and how “Alligator Blood” became a core value * What makes a startup uninvestable in today’s market Whether you’re a founder chasing product-market fit, an operator scaling go-to-market, or an investor backing AI-native vertical plays this one’s packed with honest frameworks, founder-level wisdom, and a forward-looking map of what’s next. Key Takeaways * Greenlight Guru scaled from 0 to $120M+ PE-backed outcome with domain-led GTM * Founder brands and media strategy were key to early traction * Category creation is a powerful tool, but only when the market needs it * AI wrappers are valid wedges — if you have a strong Phase 2/3 * The best vertical SaaS companies build for workflow, not just data * Speed + specificity > size in early-stage markets * Culture should be built like a product from day one * TipTop looks for wedge clarity, domain edge, and $50B+ TAMs ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

Is CLM Dead? Rebuilding Legal Infrastructure in the Agentic AI Era With Simon McCarthy

On this episode of The Vertical SaaS Podcast, host Gavin Savage sits down with Simon McCarthy, VP of Enterprise Transformation at ContractPod AI, to unpack what’s broken in Contract Lifecycle Management and what’s coming next. With over 150 CLM implementations under his belt, Simon shares a brutally honest take on why most platforms fail, the myths around CLM as a “legal” tool, and how AI is reshaping the contract stack. From post-signature ROI to the rise of agentic contracting, he offers sharp insights into where legal tech is headed and how operators can actually get it right. We explore: * Why half of CLM projects fail and how to avoid becoming a cautionary tale * The true cost of doing nothing in contract management * What makes vertical SaaS fragile in the era of AI * Whether “intelligent contracting” is just rebranding or something deeper * The line between tools and platforms, and how AI could redraw it Whether you’re scaling a legaltech product or rethinking your enterprise contract stack, this one’s packed with hard truths, practical wisdom, and a hopeful look forward. KEY TAKEAWAYS: * Simon has led 150+ CLM rollouts across major enterprises * Change management, not tech, is the CLM killer * CLM is a cross-functional platform, not just for legal * Bad implementations can cost millions in sunk value * AI + agentic tools are transforming the CLM stack * Real value lies after the signature, in tracking, obligations, and outcomes * Adoption hinges on integration and user behavior, not features * The future is modular, intelligent, and AI-native ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.

Beyond the Contract: Agentic AI, Adoption and Burnout. How AI Is Shaping In-House Legal in 2025 - with Richard Mabey, CEO of Juro

In this packed episode, Host Gavin Savage sits down with Richard Mabey, former M&A lawyer at Freshfields and now one of the leading voices in legaltech, to unpack the most urgent issues and transformative trends reshaping the legal profession in 2025. Richard is the co-founder and CEO of Juro, an AI-native platform trusted by over 6,000 companies worldwide, including major global brands and Fortune 500 enterprises. It enables legal and business teams to draft, agree, and manage contracts in a single collaborative workspace, helping users close deals up to 10x faster than traditional workflows. Together, Gavin and Richard walk through Juro’s freshly published State of In-House Legal 2025 report, dissecting the data behind rising burnout, the accelerating adoption of AI, and the cultural mismatch between what in-house teams need and what law firms still deliver. From Richard’s founder journey to the emergence of agentic AI, this is a sharp, data-driven, and human-first look at where legal is heading next, and what it will take to build both scalable tech and sustainable teams. In this episode, we get into: 💥 Why in-house burnout is rising 🤖 What Agentic AI really means for legal teams. Not just smarter tools, but autonomous systems reshaping how work gets done ⚖️ Why BigLaw is losing ground with GCs 📉 The fall of the billable hour 🧠 Building legaltech that actually sticks 👥 Culture, leadership, and the cost of 10 pm Slack messages So much of the legal industry is being reimagined faster than most teams can adapt. This episode goes beyond the hype to explore what’s breaking, what’s working, and what’s next for legal leaders navigating real pressure in real time. ---------------------------------------- Hosted on Acast. See acast.com/privacy [https://acast.com/privacy] for more information.