A VC and a Founder intellectually spar on Vertical Tech & AI: covering the latest news, unpacking in-depth business strategies, and interviewing world-class leaders in the space, every Thursday.
What Happens When AI Can Copy Your Software? | Coyne Lloyd
What happens to your software company when a competitor can rebuild your entire product over a weekend?
For vertical SaaS founders, that question is becoming increasingly difficult to ignore.
In this episode of Verticals, Luke sits down with Coyne Lloyd, founding team member at SnapDocs, former partner at Fractal, and co-founder of multiple vertical software businesses, to explore what actually makes a software company defensible in the age of AI.
At SnapDocs, Coyne helped build a business that could charge 5-10 times more than competing products, not because its code was impossible to replicate, but because competitors couldn't easily reproduce its marketplace, proprietary data, and network effects.
Now, as AI makes software development dramatically cheaper, Coyne argues that founders need to rethink what they're actually building.
They discuss:
- Why AI is eroding software complexity as a competitive advantage
- The thought experiment every vertical SaaS founder should run
- How SnapDocs built defensibility through marketplace dynamics and proprietary data
- Why hardware lock-in might be overrated
- Why AI could make industry-specific operational knowledge more valuable
- The flood of new competitors coming for vertical software markets
- Coyne's bullish and bearish predictions for public vertical SaaS companies
If you're building, operating, or investing in vertical SaaS or AI, this conversation offers a framework for figuring out which businesses will survive, and which could become more valuable than ever.
🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference (https://verticalsaasgroup.com/conference)
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🎬 TIMESTAMPS:
00:00 Intro
03:07 Why vertical SaaS founders are panicking about AI
05:12 How SnapDocs charged 5-10x more than competitors
08:43 The thought experiment every SaaS founder needs
09:29 Why hardware lock-in is an overrated moat
13:14 How SnapDocs built its marketplace and data moat
19:09 Can proprietary AI workflows create process power?
21:56 Why your biggest AI threat might not be OpenAI
29:32 Should SaaS founders sell their proprietary data?
32:33 Will AI destroy embedded software businesses?
38:58 Can startups beat incumbent vertical SaaS companies?
45:49 Why software graveyards are ideal rollup markets
49:24 What Coyne got wrong about AI rollups
52:14 Should vertical SaaS price on outcomes?
54:48 The private vertical software company Coyne is bullish on
TOPICS
1. AI Moats, Proprietary Data & Network Effects
2. Vertical SaaS, AI Disruption & Future of Software
3. AI Startups, Vibe Coding & Software Competition
4. AI Rollups, Embedded Software & Vertical AI Business Models
7 Oct 2026
Why Voice AI Is About to Change Every Vertical | Mike Sharp
Voice AI is getting dramatically better.
But simply adding an AI receptionist to your product isn't going to create a moat.
In this episode of Verticals, Luke and Nic sit down with Mike Sharp, founder and CEO of DialStack, to unpack what the next wave of voice AI actually looks like, and why vertical software companies may have a unique opportunity to own it.
Mike has spent roughly two decades at the intersection of telecom and SaaS. He previously co-founded Jive Communications, grew it to roughly $100 million in ARR, and later worked inside a healthcare software rollup with 17 brands.
Those experiences led him to a simple conclusion: the phone is still one of the most important (and most underutilized) surfaces in vertical software.
Mike explains how voice AI can evolve from answering missed calls to routing customers, completing transactional workflows, assisting employees in real time, automatically documenting conversations, and eventually becoming an entirely new interface for vertical software.
In this episode, they discuss:
-Why every vertical SaaS company should be thinking about voice AI
-Where the real moat in voice actually lives
-Why simply adding an AI receptionist isn't enough
-The voice AI use cases that are actually working today
-Why consumers hate some AI agents but love others
-When AI should replace humans—and when it shouldn't
🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference
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🎬 TIMESTAMPS:
00:00 Intro
03:29 Why vertical SaaS should own the phone
11:32 The voice AI use cases actually working today
23:00 The overlooked opportunity in ambient voice AI
28:32 Why voice AI is harder than text AI
40:07 Why vertical SaaS hasn't fully embraced voice yet
47:00 Why vertical-specific voice AI could win
51:20 The most interesting voice AI use cases
54:36 Where the next voice AI boom could happen
TOPICS
1. Voice AI & AI Agents
2. Vertical AI & Vertical SaaS
3. Embedded Voice & Telephony Infrastructure
4. AI Agents, Ambient AI & Business Automation
5. Proprietary Data, AI Moats & Systems of Record
30 Sept 2026
How to Build a Vertical SaaS Sales Machine | Kevin Wilson
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 Verticals, Luke sits down with Kevin for a tactical masterclass on vertical go-to-market – where the traditional SaaS sales playbook works, where it breaks, and what founders should do instead.
Kevin explains why he almost never recommends hiring 10 sales reps immediately after raising a round. Instead, he hires in groups of two or three, watches the underlying economics, and scales only when the existing motion proves it can support more people.
But hiring is only part of the equation.
Kevin breaks down exactly what he looks for in sales leaders and AEs, why industry experience is dramatically overrated in sales, and the interview tests he uses to identify great candidates before they join.
They cover:
-When a startup is actually ready to scale sales
-Why founders shouldn't outsource go-to-market fit
-Why Kevin always hires sales reps in groups of two or three
-The metrics he watches before adding more headcount
-Why founders should never completely leave the sales process
-How to hire your first great Head of Sales
-The four traits Kevin looks for in every AE
If you're a vertical SaaS or vertical AI founder trying to go from founder-led sales to a repeatable go-to-market machine, this episode is packed with tactics you can actually use.
🎟️ TICKETS DROPPED. Vertical Software Summit — 5-billion-dollar Vertical AI CEOs confirmed to speak. Snag a ticket before they're gone: https://verticalsaasgroup.com/conference
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🎬 TIMESTAMPS:
00:00 Intro
01:53 Kevin's path from banking to vertical SaaS
06:59 When are you actually ready to scale sales?
08:41 Why hiring 10 AEs at once almost never works
10:31 Why founders should never completely leave sales
16:07 How to hire a great Head of Sales
25:21 The 4 traits Kevin looks for in every sales rep
29:16 Why industry veterans often fail in sales
34:40 Can you spot a bad sales hire in one week?
37:27 How to sell into a small, finite vertical market
42:32 The biggest AI opportunity in sales right now
51:32 Kevin's AI go-to-market tech stack
TOPICS
1. Vertical SaaS Go-To-Market & Sales Strategy
2. SaaS Sales Hiring, Scaling & Leadership
3. Founder-Led Sales & Go-To-Market Fit
4. Vertical SaaS Outbound, ICP & Demand Generation
5. AI Sales Automation, CRM & RevOps
Who has been a guest on Verticals: A Weekly Biz Show
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Quinn Litherland
Yoni Rechtman
Sahill Poddar
Rick Zullo
Alex Oppenheimer
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