S2E3: Vertical SaaS 3.0 – Nick Tippmann on Why SaaS Isn’t Dead, It’s Just Getting Specific

In the next era of enterprise software, general-purpose tools are fading. Verticalization is no longer a niche strategy. It's the battleground. And at the forefront is Nick Tippmann, founder and GP at TipTop Ventures, who’s betting on a new generation of software: intelligent, embedded, and purpose-built for specific industries. It’s not just SaaS anymore, it’s Vertical SaaS 3.0.

From his operator roots in the Midwest to his front-row seat at Greenlight Guru, Nick’s journey is a playbook for how specialization, fintech integration, and now AI are reshaping the software stack. And like all the best founders-turned-investors, he’s building the fund he wishes had backed him.

Before founding TipTop Ventures, Nick helped scale Greenlight Guru, a Vertical SaaS pioneer serving the MedTech industry. He wasn’t just along for the ride, but building the playbook. As CMO and part of the founding team, he saw firsthand how purpose-built tools outperformed horizontal solutions by deeply understanding workflows, regulations, and customer pain points.

That experience seeded a thesis: vertical software wins not just by focusing on one market, but by embedding itself into the core operations of that market. Add payments, financial services, and now you don’t just have a better tool. You have a platform that redefines the job.

TipTop backs Vertical SaaS founders at pre-seed and seed with a vertical focus. Every investment aligns with TipTop’s core belief that the future belongs to software built for one specific customer, not every customer. Looking at SaaS + Fintech + AI, they invest in companies that don’t just offer software, but reimagine workflows, automate decisions, and create new revenue streams through embedded finance.

TipTop Fund I is a $15M pre-seed and seed-stage vehicle targeting 35 investments over three years with $100K–$400K initial checks. No follow-ons, but just SPVs in winners. The portfolio already includes companies like:

* GC AI: AI platform for in-house legal

* Frontiers MarketL SaaS-enabled marketplace for cattle ranchers

* Revin: AI ops for home services

To understand where TipTop is going, you have to understand where SaaS has been.

* SaaS 1.0: Pure cloud: industry-agnostic tools like Salesforce and Zoom.

* SaaS 2.0: Verticalization: products like Toast and ServiceTitan that go deep in one sector.

* SaaS 3.0: The new frontier. Vertical software powered by AI and embedded finance, capable of replacing entire workflows. Not just digitizing them.

In this model, AI isn’t just an add-on. It’s the engine. It handles documentation, compliance, forecasting, even underwriting. And because these companies own the data and the transaction layer, their defensibility compounds.

As Nick puts it: “The best Vertical SaaS companies don’t stop at software—they become agentic operating systems.”

We’re now at an inflection point. As AI reshapes horizontal tools, mid-market SaaS is being squeezed. Generic is getting commoditized. Meanwhile, vertical winners like Owner.com (113% YoY Growth Rate) are proving that depth, not breadth, is where the margin lives.

Markets like construction, elder care, commercial trucking, and specialty manufacturing are ripe for this kind of disruption. And founders with deep domain knowledge are realizing that the future isn’t just building for an industry, but rather that it’s building into it.

Nick’s view? This isn’t a trend. It’s a structural shift. And the best GPs will be those who can underwrite it before the category has a name.

Where some funds chase logos, TipTop builds trenches. Their edge lies in deep market mapping before deployment and a tight knit LP and operator community to support founders early.

They’re not just investing in tools. They’re investing in teams who know the customer better than anyone else, and can move faster than legacy players weighed down by horizontal bloat.

As more GPs enter the verticalization conversation, TipTop’s early bets, operator DNA, and structured strategy give it a head start. In a world chasing breadth, they’re choosing depth, and building a portfolio that reflects it.

For LPs, founders, and operators watching the future of SaaS unfold, one thing’s clear: Vertical SaaS 3.0 isn’t coming. It’s already here. And Nick Tippmann is betting early.

Special thanks to John Gleeson (Success VP) for connecting us to Nick!

To hear more, visit slicefund.substack.com