SaaS Apocalypse: Jes Lipson Shares His Thoughts on how SaaS founders can navigate the chaos in the SaaS market.
Jes joins me to break down the SaaS valuation collapse, introduce two tests every SaaS founder should run on their business, and explain why the buy vs. build equation has permanently shifted
The SaaSpocalypse is real, but it's also starting to create separation. Some SaaS companies are emerging stronger while others stall, and the difference isn't whether you've frankensteined on some AI features. Jes has been thinking about this a ton and has some great ideas for other NC SaaS founders working through this tough time (funding and valuation-wise): Jes Lipson shares two clear tests he's using to pressure-check his own business, I add a third, and together we map out what it actually takes to come out the other side.
In this very short episode (~20mins), we do cover a couple of slides you can access here that will enhance your viewing/listening experience→
We couldn’t bring you 100% original founder-to-founder content like this without the support of our awesome-sauce sponsors:
Loving our content? It wouldn’t be possible without our amazing sponsors and our paid subscribers, so THANK YOU!
Featured Platinum Sponsor
Featured Gold Sponsor
Featured Silver Sponsor
And special thanks to our friends at Walk West for partnering with us to produce this pod!
Who is Jes?
Jesse Lipson is the founder and CEO of Levitate AI, a relationship marketing platform built for micro SMBs. Think independent lawyers, financial advisors, nonprofits; Levitate has nearly 9,000 customers and over 300 employees. Before Levitate, Jes founded ShareFile, one of the earliest SaaS companies in the Triangle, which he sold to Citrix and eventually grew into a billion-dollar business before it was acquired by Progress Software. At Citrix, he expanded his remit to run the company's entire SaaS portfolio, giving him a rare vantage point across dozens of different software models. He started Levitate in 2017, originally called Levitate.ai, a name that was ahead of the available technology, and has been navigating the AI era with that same long-arc perspective ever since.
I did a longer-form deep dive with Jes back in November 24 if you want to hear his entire founder’s journey, which I strongly recommend→
Tweener Talks: Jesse Lipson - A Legendary Triangle Founder
When you look at the list of people that have the biggest impact on the Triangle’s startup ecosystem, Jes Lipson is in the top 5. Not only is he a serial founder, but founding Raleigh Founded has had a profound impact by giving local startups not only a place to work, but a community that supports them, educates them and has a lot of success launching …
Highlights
The removal test: If you remove AI from the product, does it still work? Investors favor companies where AI is core to the product, not an add-on feature.
Growth re-acceleration beats raw growth: A company accelerating from 10% growth to 30% is viewed more favorably than one slowing from 100% to 40%, because trajectory signals AI-driven momentum.
AI features are not a moat: Building lots of AI features is now expected. Companies relying on AI features alone are still getting disrupted.
Public SaaS multiples have collapsed: Major SaaS companies have seen significant valuation compression:
The “vibe coding” churn signal: If customers are replacing your software by building their own AI-generated alternatives, that’s a major warning sign. The build-vs.-buy equation has shifted dramatically.
The fear index: A useful test for founders:
Levitate’s newest AI bet: A forthcoming product focused on helping tens of thousands of small businesses actually implement AI and transform workflows—not just learn about AI.
MCP is becoming table stakes: Levitate launched an MCP server and is upgrading its API because customers increasingly expect seamless integration with AI assistants like Claude.
Software + services is more defensible: Pure SaaS businesses face growing pressure from AI. Combining software with services creates stronger customer relationships and greater resilience.
Every conversation with Jes is a reminder that the best operators don't just read the environment; they build a strategic framework, formulate tactics and KPIs and then relentlessly execute.
Where to Watch/Listen:
Visit Tweener Talks to listen for all audio podcast players
We have a video version on YouTube (make sure to subscribe!)
📌 What’s Next
Subscribe to NC Tweener Talks for more conversations with North Carolina founders, operators, and builders shaping the future of the ecosystem. Paid subscribers help us keep creating more episodes, events, and founder-focused content across the state.