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.

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

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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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Summary

In this episode of the Vertical SaaS podcast, Gavin Savage interviews Jessica Chen-Riolfi, co-founder of Uprise, an AI-driven financial advisory platform for small business owners. Jessica shares her journey from Wall Street to Silicon Valley, her experiences at major tech companies like eBay, TransferWise, and Robinhood, and the lessons that shaped her approach to founding Uprise.

She discusses the complexities of financial decision-making for small business owners and how Uprise aims to address these challenges through technology and AI. The conversation also touches on the regulatory landscape in financial advisory and the importance of doing right by customers. In this conversation, Jessica Chen Riolfi discusses the complexities of securities compliance, the importance of human oversight in AI, and her journey in finding co-founders. She shares insights on the highs and lows of entrepreneurship, navigating venture capital, and the significance of angel investors.

Jessica emphasizes the need for learning and iterating in business, building product-market fit, and the future goals of her company, Uprise. She also explores innovations in fintech partnerships and offers valuable advice for founders.

Takeaways

Jessica's journey reflects a winding path to tech.

The importance of stepping outside of comfort zones.

Big tech experiences shape startup founders' approaches.

Uprise aims to solve complex financial decision-making.

AI technology is crucial for modern financial advisory.

Partnerships enhance Uprise's service offerings.

Understanding the intertwined nature of personal and business finances.

Regulatory compliance is essential in financial advisory.

Building from scratch allows for tailored solutions.

Listening to customer feedback is vital for improvement. Securities can be complex and often misunderstood.

Human oversight is crucial in AI-generated outputs.

Finding the right co-founders can be challenging but essential.

Best practices in entrepreneurship evolve over time.

Understanding your market is key to product development.

Venture capital can be beneficial but requires careful navigation.

Angel investors provide valuable support and networks.

Learning quickly from failures is vital for startups.

Building product-market fit takes time and experimentation.

Fundamentals like revenue and profit should guide business decisions.

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Summary

In this episode of the Vertical SaaS Podcast, Host Gavin Savage interviews Blakely, the Chief Strategy Officer of Redo, who shares his extensive journey through the tech and startup landscape. Blakely discusses his transition from a corporate environment at Dell to the fast-paced world of startups, highlighting his experiences at Instructure and Divvy, where he played pivotal roles in scaling these companies.

He also introduces Redo, a new venture focused on simplifying e-commerce returns, and shares insights on the current market dynamics affecting startups, particularly in relation to interest rates and innovation. In this conversation, Blakely discusses his multifaceted role at Redo, emphasizing the importance of product management, finance, and operations in a startup environment. He shares insights on identifying companies poised for rapid scaling, the nuances of vertical versus horizontal SaaS, and the challenges of product expansion.

Additionally, he offers valuable advice for career advancement in startups, highlighting the significance of impact, leadership, and understanding business value drivers.

Takeaways

• Blakely transitioned from a corporate job to startups for a faster pace.
• His career began at Dell, but he found fulfillment in startups.
• At Instructure, he proposed a go-to-market strategy that was implemented immediately.
• Scaling a startup feels chaotic, like a rocket ship losing parts mid-flight.
• Having 'scar tissue' from past experiences helps in navigating challenges.
• The importance of connections in job searching cannot be overstated.
• The startup environment is currently challenging but fosters innovation.
• Redo aims to simplify e-commerce returns without charging SaaS fees.
• Market dynamics have shifted, making it harder for startups to thrive.
• Bundling services is becoming more common as money becomes scarce. My role has become something like if product, operations, and finance had a baby.
• We think of ourselves almost like a VC investing in these different startups.
• I care a ton about the people that are involved.
• You can't just be better, you have to be different.
• It's a true meritocracy. Best people, more money, more equities, please stay.
• You need to crush it.
• If you want to grow a lot in your career, you got to hitch your wagon to the really good leader.
• We're building a platform that's going to be multiple products.
• You need to understand what matters to the business.
• I have seven mini CEOs at the company.

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In this episode, Host Gavin Savage interviews Alun Baker, a seasoned growth and transformation specialist who has led over $1.6 billion in transactions, 3 successful exits, and guided 5 companies onto the Times Fast Track Growth list. Currently serving as Executive Chairman at Solidatus, a leader in data lineage and governance, Alun shares invaluable insights into scaling vertical SaaS businesses, navigating M&A, and staying ahead in the evolving SaaS landscape.

What’s discussed:

• Building for scale: Early indicators that a vertical SaaS company is ready for rapid growth.
• M&A mastery: Lessons from successful exits and preparing niche companies for acquisition.
• AI's disruption: How vertical SaaS can unbundle horizontal giants using domain-specific AI.
• Cultural balance: Integrating domain experts with tech teams while scaling efficiently.
• Advice for founders: Strategies for navigating funding, growth, and leadership challenges in 2024.

Whether you're a founder, an executive, or a SaaS enthusiast, this episode is packed with actionable advice for building and scaling in niche markets.

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Summary

In this episode of the Vertical SaaS Podcast, hosts Gavin Savage and Ben Brown welcome Eli Bozeman, Assistant Vice President of Product at SageSure. The conversation explores Eli's and Ben's career journeys, insights into the Insurance market, and the evolution from Insurtech 1.0 to 2.0. They discuss the challenges of product growth in the insurance industry, the importance of accuracy, and the innovative approaches at SageSure to enhance the insurance experience. The episode highlights the significance of collaboration between technology and product teams in driving success in the InsureTech space. In this conversation, Eli and Ben discuss the intricacies of product leadership in the insurance industry, focusing on the importance of building proprietary models, maintaining team culture, and balancing speed with innovation. They share insights on growth challenges, the significance of curiosity in high-performing teams, and the evolving landscape of insurance technology. The discussion highlights the need for collaboration between product and engineering teams and the excitement surrounding the industry's future as it embraces new technologies like AI.

Takeaways

• Eli Bozeman has a diverse background in tech and insurance.
• Ben Brown transitioned from investment banking to tech leadership.
• Insurtech 2.0 is characterized by experienced disruptors.
• Understanding industry complexities is crucial for growth.
• Direct-to-consumer models can attract the wrong risk.
• SageSure is focused on innovative insurance product development.
• Accuracy in insurance metrics is vital for success.
• Collaboration between tech and product teams enhances outcomes.
• AI is being integrated to improve insurance processes.
• The insurance industry is evolving with new technologies and approaches. The insurance industry requires a balance of proprietary models and vendor evaluations.
• Maintaining a strong team culture is critical for innovation.
• Speed and iteration are essential in product development.
• Creating a framework for learning helps in overcoming fears of failure.
• Trust between product and engineering teams fosters collaboration.
• Curiosity and a desire to solve difficult problems are key traits of high performers.
• Insurance is evolving and can leverage machine learning effectively.
• Retention of team members is as important as hiring new talent.
• Educating team members about industry nuances is crucial for success.
• The future of insurance is promising with advancements in technology.

Keywords

Vertical SaaS, Insurtech, product innovation, insurance technology, growth metrics, insurance industry, technology leadership, collaboration, insurance, product leadership, innovation, team culture, machine learning, growth, collaboration, AI, high performance, industry insights

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Summary

In this episode of the Vertical SaaS podcast, Gavin Savage hosts Jeremy Parker and Jamil Jaoui from Jitterbit. They discuss their backgrounds, the mission of Jitterbit, and the importance of integration solutions in today's digital landscape. The conversation delves into leadership strategies, sales performance, the role of AI in business, and the challenges faced by startups in scaling operations. The guests share insights on mentorship, team dynamics, and the future of automation, emphasizing the need for collaboration and alignment within organisations.

Takeaways

• Jitterbit provides a low-code, AI-infused platform for digital transformation.
• The integration of various SaaS applications is crucial for business efficiency.
• Leadership requires breaking down silos and aligning team objectives.
• Sales performance is influenced by trust in processes and humility.
• Mentorship plays a vital role in personal and professional growth.
• AI infusion can accelerate business processes and reduce IT burdens.
• Startups often struggle with application sprawl and integration challenges.
• A strategic partnership approach is essential for successful implementation.
• Change management is critical in scaling operations effectively.
• Transparency in data helps in making informed decisions and coaching teams

Chapters

00:00: Introduction and Guest Backgrounds

03:05: Understanding Jitterbit's Mission and Market Position

06:00: The Role of the COO in Scaling Operations

08:45: Leadership Insights and Team Alignment

12:09: Sales Performance and Team Dynamics

15:01: Navigating Challenges in Sales and Management

18:04: The Importance of Mentorship and Growth

21:10: AI Infusion and Its Impact on Business

23:49: Integration Challenges for Startups

27:03: Future of Automation and Integration Solutions

Keywords

Jitterbit, AI infusion, digital transformation, sales performance, leadership, integration solutions, mentorship, business scaling, automation, startup challenges

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Summary

In this episode of the Vertical SaaS podcast, Gavin Savage interviews Karl Seelbach, a legal tech entrepreneur and managing partner of a law firm. They discuss Karl's journey from a small-town upbringing in Texas to founding Skribe AI, a company focused on modernising the legal industry through technology. The conversation explores the challenges and opportunities in legaltech, the impact of AI on the legal profession, and the future of legal services. Karl shares insights on the importance of education in technology adoption and the potential for significant cost savings and efficiency improvements in legal processes.

Takeaways

• Karl Seelbach's journey from a small town to legal tech entrepreneur.
• The importance of technology adoption in the legal industry.
• Skribe AI aims to modernise how attorneys capture and analyse testimony.
• AI can significantly reduce costs and time in legal processes.
• Education is crucial for successful technology implementation in law firms.
• The legal tech market is largely untapped and presents significant opportunities.
• COVID-19 accelerated the adoption of technology in the legal sector.
• Plaintiff attorneys have a different incentive structure compared to defense attorneys.
• AI can assist in claims management and improve efficiency for insurance companies.
• The future of legal tech will involve a balance between human touch and automation

Keywords

Legal Tech, Skribe AI, AI in Law, Technology Adoption, Legal Disposition, Legal Innovation, Personal Injury Law, Legal Industry Trends, Future of Law, Technology in Legal Services, Legal Automation

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Summary

In this episode of The Vertical SaaS podcast, Gavin Savage interviews Cain Elliott, the Chief Legal Futurist at Filevine. They discuss the transformative role of AI in legal tech, the challenges and opportunities within the industry, and the importance of innovation and client feedback. Cain shares insights on the evolution of legal tech, the impact of AI on legal work, and the future of legal services, emphasizing the need for quality and engagement in legal processes. He also reflects on leadership lessons and the importance of collaboration in tech startups.

Takeaways

• Cain Elliott is the Chief Legal Futurist at Filevine, focusing on legal innovation.
• Legal tech is defined as technology that lawyers use, evolving rapidly post-COVID.
• AI is reshaping the legal landscape, making processes more efficient.
• Client feedback is crucial in developing legal tech solutions.
• Filevine's innovations include tools like deposition co-pilot to enhance legal workflows.
• The legal tech market is competitive, requiring companies to differentiate themselves.
• Quality of work and client outcomes are paramount in legal services.
• Leadership in tech startups requires collaboration and understanding of various roles.
• The future of legal services may involve more consumer access and alternative dispute resolution.
• Human interaction remains essential in legal tech, especially post-pandemic.

Keywords

Legal Tech, AI, Innovation, Filevine, Legal Services, Technology, Law Firms, Automation, Leadership, Startups

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Summary

In this engaging conversation, Gavin Savage interviews Nic Poulos, founder and managing partner at Euclid Ventures, discussing the evolution and significance of vertical SaaS. Nic shares his journey from investment banking to becoming a prominent investor in vertical software, highlighting the growing demand for specialized software solutions in various industries. The discussion covers the differences between vertical and horizontal SaaS, current trends in the market, common pitfalls for startups, and the importance of domain expertise in building successful teams. Nic emphasizes the need for founders to deeply understand the problems they are solving and the value of validating customer pain points before seeking investment.

Takeaways

• Nic Poulos is a serial vertical software investor.
• Vertical SaaS focuses on specialized software for specific industries.
• The cost to build software has drastically decreased over the years.
• Vertical software companies often have higher sustainability of growth.
• Understanding the current solutions in the market is crucial for founders.
• Domain expertise is essential for success in vertical SaaS.
• Velocity in execution is key for early-stage startups.
• Hiring industry experts can enhance communication with customers.
• Investors look for a deep understanding of the problem being solved.
• Validating customer pain points before building product is vital

Keywords

Vertical SaaS, Nic Poulos, software investment, startup mistakes, domain expertise, team building, venture capital, industry trends, B2B, B2BC software, technology innovation

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