HeyJaredVerticals: A Weekly Biz Show On Vertical AI
A VC and a Founder intellectually spar on Vertical Tech & Vertical AI: covering the latest news, unpacking in-depth business strategies, and interviewing world-class leaders in the space, every Wednesday.
- Indexed videos, last 90 days
- 39
- Latest publication
- Sep 30, 2026
- Audience
- ~6.8K subscribers
- Earliest in this view
- Jul 5, 2026
Latest videos
How to Build a Vertical SaaS Sales Machine | Kevin Wilson (opens the original)
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Most SaaS founders think scaling sales means hiring more salespeople. Kevin Wilson thinks that's exactly how you get into trouble. Kevin is the CRO of Skimmer, the software platform used by thousands of pool service companies across the US. Before Skimmer, he helped scale multiple vertical software businesses from founder-led sales and pre-revenue stages to tens of millions in ARR. And along the way, he's developed a very different playbook for selling vertical software. In this episode of Verti
The Brutal Divide in Today’s Market | Alex Oppenheimer (opens the original)
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Raising a seed round right now feels brutally polarized. The hottest startups can raise on three slides, while companies in the middle face “Death Valley.” In this clip from Verticals, Alex Oppenheimer gives a reality check for founders navigating today’s venture market. nic poulos luke sophinos vertical software ai business business podcast business advice entrepreneur entrepreneur podcast startup podcast startup advice verticals podcast vertical ai vertical saas alex oppenheimer
Why Timing Matters More Than a Great Startup Idea (opens the original)
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Timing can determine whether a company succeeds or fails. In this clip from Verticals, Alex Oppenheimer, Founder & General Partner at Verissimo Ventures, explores why ideas that failed years ago may work later, why pre-seed founders need to “survive to iterate,” and how premature hiring and aggressive sales can hurt before the product or market is ready. Watch the full episode with Alex Oppenheimer! nic poulos luke sophinos vertical software ai business business podcast business advice entrepren
When Outcome-Based Pricing Fails | Zach Rosen (opens the original)
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Vertical software founders often want to price around outcomes, but delayed, low-probability risks can make that model misaligned with customer needs. If the value is preventing a future clawback, monetizing only when the event happens creates the wrong incentives. In this clip from Verticals, Zach Rosen explains why Brellium uses usage-based pricing instead: a per-patient visit rate bundled into a recurring subscription, with a premium for clawback protection. nic poulos luke sophinos vertical
The Two Vertical Software Playbooks (opens the original)
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Vertical software founders typically face two paths: compete directly with the system of record, or build a wedge so strong that the incumbent can’t realistically match it. In this clip from Verticals, Zach Rosen, CEO at Brellium, explains how outside data can create a network effect and support a powerful compliance platform. nic poulos luke sophinos vertical software ai business business podcast business advice entrepreneur entrepreneur podcast startup podcast startup advice verticals podcast
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Audience
~6.8K subscribers
Measured Sep 19, 2026
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