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

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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.

• 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

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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.

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In this episode, Gavin Savage sits down with Arik Yelovitch, co-founder of Adaptive Insurance, to talk about the intersection of AI, fintech, climate tech, and Vertical SaaS 3.0. From his early days at Hippo and Delos to launching Adaptive, Arik shares a candid look at the real challenges, and opportunities facing modern startup & Insurtech founders.

They dig into what it means to build a purpose-driven startup in today’s environment, including:

• 🚀 The vision behind GridProtect, Adaptive’s first product, built for power outages and other short-duration climate events
• 🧠 How AI and automation are reshaping risk modeling and claims
• 🏗️ What Vertical SaaS 3.0 really means: purpose-built software + fintech + AI
• 📉 Fundraising today vs. 3 years ago: what’s changed, and how to raise smarter
• 💸 Secrets to hiring top-tier talent on a startup budget (and what comp looks like early)
• 🚀 The vision behind GridProtect, Adaptive’s first product, built for power outages and other short-duration climate events
• 📉 Fundraising in 2025 vs. 2021: what’s changed, and what still works
• 🔧 The rise of "vibe coding" and AI-assisted development
• 🌱 Why Adaptive sees climate insurance as the ultimate vertical for Vertical SaaS 3.0

Whether you're building in Insurtech, investing in climate resilience, or scaling a startup, this is a must-listen.

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In this episode, host Gavin Savage is joined by Matheus Riolfi, co-founder and CEO of Tint, the embedded insurance platform powering companies like Turo, Deel, and Montway. Together, they unpack why insurance shouldn’t be a standalone experience but rather a seamless feature inside the products we already use and love.

Matheus reflects on his time scaling international markets at Turo, where insurance quickly became the most complex and critical piece of expansion. That firsthand frustration sparked the idea for Tint: a full-stack platform built to let any SaaS company or vertical marketplace embed insurance natively and intelligently. As Matheus says, “Insurance is essential—but nobody wants to think about it. It should just come with the product.”

This conversation is a deep dive into how embedded insurance is evolving from buzzword to business model. Matheus shares:

• The “aha moment” in a Canadian taxi ride that made him realize insurance could be bigger than Turo itself
• How platforms in mobility, vacation rentals, and logistics are tapping into insurance as a powerful value-add
• Why embedded financial products are the next phase of SaaS monetization
• How AI is finally making insurance smarter, faster, and radically more personalized
• What’s changed in the last year that’s finally accelerating real-world adoption
• And why execution not just vision is what separates winners from hype

If you’re building in vertical SaaS, insurtech, or exploring new monetization paths for your platform, this is a front-row look at how one of the most traditionally overlooked and under-innovated industries is being reimagined from the inside out.

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In this episode of The Vertical SaaS Podcast, Gavin Savage sits down with Patricia Gannon, founder and CEO of Platforum9, a voice-first platform reimagining how the legal community connects, learns, and grows. Patricia shares her incredible journey from a small village in Ireland to building one of the largest law firms in the Balkans and why she’s now focused on using voice tech to democratize access to legal knowledge and mentorship.

They dive into the challenges young lawyers face today, from lack of mentorship to outdated training models, and explore how platforms like Platforum9 can foster more meaningful engagement across the legal profession. Patricia also shares her perspective on the future of AI in law, why the billable hour model is overdue for reinvention, and how community-building can drive real innovation in the space.

Whether you’re a legaltech founder, early-career lawyer, or just curious about where the future of legal practice is headed, Patricia’s story offers powerful lessons in leadership, inclusion, and purpose-driven entrepreneurship

Key Words

LegalTech, Voice Technology, AI in Law, Legal Innovation, Legal Community, Young Lawyers, Legal Education, Billable Hours, Mentorship, Entrepreneurship, Legal SaaS, Platforum9

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Summary

In this episode of The Vertical SaaS Podcast, Gavin Savage sits down with Ned Gannon, Co-Founder and CEO of Coheso, an AI-powered legaltech startup transforming how in-house legal and compliance teams work. Ned shares his journey from corporate attorney to legaltech entrepreneur, including his successful exit from previous startup called eBrevia, before launching Coheso.

Together, they explore how AI, especially agentic AI is reshaping legal operations, the evolving metrics in the space, and why domain expertise is still key. Ned also opens up about the challenges of building a legaltech company today versus a decade ago, and how Coheso acts as a legal front door for businesses, streamlining workflows and capturing tribal knowledge that helps legal teams move faster with confidence.

Whether you're a founder, in-house counsel, or tech-curious legal pro, this episode offers a front-row seat to the changing metrics, team dynamics, and future of AI in legal.

Key Words

LegalTech, AI, Legal Innovation, Agentic AI, Legal SaaS, In-house Counsel, Legal Automation, Cohiso, eBrevia, Legal Compliance, Entrepreneurship, Technology in Law

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In this episode of The Vertical SaaS Podcast, Gavin Savage sits down with Clement Cazalot, CEO of Machinery Partner, to explore his journey into technology and entrepreneurship. They discuss how Machinery Partner evolved from a Craigslist-style marketplace to a full-service B2B platform, the importance of deeply understanding customer needs, and the challenges of scaling in a niche market.

Clement shares insights on leadership, team dynamics, and the role of AI in optimizing core SaaS metrics. They also dive into sales strategies for vertical SaaS, the balance between domain expertise and adaptability in hiring, and the evolving landscape of venture capital. The conversation highlights the transformative impact of AI on industrial markets and B2B Marketplaces, the need for hyper-customization in vertical SaaS, and how startups can stay agile in a rapidly changing environment.

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In this episode of The Vertical SaaS Podcast, host Gavin Savage sits down with Frederik Muelke, Head of Alternative Assets at Robin AI, a Legaltech startup leveraging AI to automate contract reviews, reduce costs, and empower legal teams.

Frederik shares his journey from corporate law to entrepreneurship, reflecting on key lessons from founding his first startup, Finzu, and the critical role of founder-market fit and talent management. He and Gavin dive into Robin AI’s mission to simplify contracts through AI, tackling the challenges of trust and adoption in legal workflows.

The conversation explores AI’s transformative impact on the legal industry - how it’s leveling the playing field for smaller firms, reshaping legal workflows, and challenging traditional models like billable hours. Frederik also offers insights into the evolving M&A landscape for 2024, emphasizing the need for specificity in legal tech solutions and the power of strategic partnerships in a rapidly changing industry.

A must-listen for anyone interested in the future of AI in legal tech and beyond.

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