Episode
Jesse Lipson, CEO & Founder of Levitate: Building AI Features Won't Save You but Here's What Will
- Podcast
- NC Tweener Talks
- Published
- Jun 25, 2026
- Duration seconds
- 1537
- Processing state
not_requested- Canonical source
- https://share.transistor.fm/s/f652c4b5
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Summary
Jess Lipson, founder and CEO of Levitate, joins host Scot Wingo for a focused, framework-driven conversation on how SaaS founders should think about their businesses in the age of AI. Jess has been building SaaS since before the category had a name. His first company, ShareFile, sold to Citrix and eventually became a billion-dollar business. At Citrix, he ran the company's entire SaaS portfolio. Now at Levitate, a relationship marketing platform serving nearly 9,000 small businesses, he's spent the last year working out a clear-eyed answer to one of the most common questions Scot hears from Triangle founders: what do you actually do about the SaaSpocalypse? In this episode, Jess introduces two tests every SaaS founder should run: the Removal Test (if you strip AI out of your product, does it still function?) and the Growth Re-acceleration Test (is your growth rate going up or down, and what does that signal to investors?). Scot adds a third indicator from what he's seeing across the Tweener Fund portfolio: churn driven by customers who are now vibe-coding their own replacements. Together, they walk through how the buy-vs.-build equation has shifted 10 to 100 times, why having AI features is now table stakes rather than a competitive advantage, and what it looks like to build a business where new frontier model releases feel like tailwinds instead of threats. Timestamps 00:00 Cold Open & Welcome 00:29 Sponsors: Robinson Bradshaw & Bank of America 01:24 Scot's Intro: The SaaSpocalypse 02:31 The February Tweener Times Piece 03:05 Why This Episode Exists 04:08 Welcome Jess Lipson 04:37 How Scot & Jess Know Each Other 05:10 Jess's SaaS Pedigree: ShareFile to Citrix 05:49 SaaS Multiples Have Collapsed 07:00 Salesforce, HubSpot & Workday Are Down Too 08:13 AI…