Verticals: A Weekly Biz Show

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.

Verticals: A Weekly Biz Show is a business podcast hosted by Luke Sophinos, with 46 episodes on record and a Required Pod Score of 80.

Luke Sophinos hosts Verticals: A Weekly Biz Show, a business show with 46 episodes published.

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  Verticals: A Weekly Biz Show

  How to Build a Vertical SaaS Sales Machine | Kevin Wilson

  Sep 30, 202654 min

  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 FOLLOW KEVIN WILSON LINKEDIN ➡️ https://www.linkedin.com/in/kevinwilsonsales FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ 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

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  Verticals: A Weekly Biz Show

  Who Wins the Vertical AI Wars? | Luke Sophinos vs Nic Poulos

  Sep 23, 202630 min

  Everyone was predicting a SaaSpocalypse. Now the data is coming in... and SaaS isn't dead. Public software has rebounded, vertical software has held up relatively well, infrastructure is surging, and consumption-based businesses are benefiting directly from the explosion of AI usage. So Luke and Nic are asking a different question: What happens next? In this episode of Verticals, there’s no guest. Instead, Luke and Nic debate the emerging battle taking place inside every software vertical. On one side are the legacy systems of record that have spent years building distribution, customer relationships and enormous proprietary datasets. On the other are a new generation of vertical AI startups moving at incredible speed, alongside AI-native services companies that can quietly enter through the back door by doing the work incumbents traditionally left to their customers. Get ready for this debate: -Why the SaaSpocalypse may have been overblown -Which software companies are actually benefiting from AI -The 4 strategies startups can use to attack SaaS incumbents -Why AI-native services could become a Trojan horse into the system of record -Whether incumbents need to own the “ChatGPT for their industry” ️ 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 FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ TIMESTAMPS: 00:00 The SaaSpocalypse is over... now what? 02:02 What the software market data actually says 05:05 How AI startups can attack legacy SaaS 10:20 Why AI-native services are such a powerful wedge 16:16 What should legacy SaaS CEOs do right now? 21:29 Can incumbents actually reinvent their products? 23:39 Is the vertical AI M&A wave finally coming? 25:14 Why AI acquisitions could accelerate 27:12 How startups can position themselves to be acquired TOPICS 1. Vertical AI vs. Vertical SaaS 2. AI Startups & Legacy Software Incumbents 3. AI-Native Services & Systems of Record 4. SaaS M&A & Vertical AI Acquisitions 5. AI Distribution, Data Moats & Specialized Models

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  Verticals: A Weekly Biz Show

  How AI Is Rewriting the Marketplace Model | Mike Duboe

  Sep 9, 202639 min

  What happens to marketplaces when buyers and sellers don't need to be human anymore? AI agents are getting increasingly capable of searching, negotiating, purchasing and eventually transacting with other agents. And according to Mike Duboe, General Partner at Greylock, that could completely reshape how marketplaces and commerce itself work. In this episode of Verticals, Luke and Nic sit down with Mike to explore why AI could make entirely new markets addressable to the marketplace model. Transactions that once required brokers, sales reps, phone calls and complex negotiations could increasingly be handled autonomously by agents. They discuss: -Which transactions consumers will actually hand over to AI -Why B2B commerce could be transformed by autonomous agents -How AI unlocks markets that were previously too complex for marketplaces -What trust and reputation look like when the buyer is an AI agent -Whether vertical SaaS and marketplaces eventually converge If you're building in vertical AI, marketplaces, B2B commerce or agentic software, this episode is a look at what happens when AI doesn't just help us shop, it starts participating in the economy itself. ️ 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 FOLLOW MIKE DUBOE LINKEDIN ➡️ https://www.linkedin.com/in/mikeduboe/ FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ TIMESTAMPS: 00:00 How AI could transform B2B commerce 02:02 Why Mike is still betting on network effects 03:43 AI is making new marketplaces possible 05:20 Which purchases should AI automate? 08:30 The opportunity for agent-to-agent marketplaces 10:02 What is a “dark marketplace”? 11:46 Why AI threatens traditional marketplace take rates 13:54 Proprietary catalogs as the new marketplace moat 16:33 Trust in a world of autonomous AI buyers 20:42 Why B2B marketplaces historically became vertical SaaS 22:55 Will vertical AI and marketplaces converge? 24:18 The massive embedded advertising opportunity 28:49 Why AI products could become ad-supported 34:26 Distribution becomes the moat when software gets easier 35:55 Mike’s framework for investing in AI marketplaces TOPICS 1. AI Marketplaces 2. Agentic Commerce 3. B2B Commerce 4. AI Agents 5. Vertical AI

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  Verticals: A Weekly Biz Show

  The AI Startup Strategy Everyone Is Copying | Quinn Litherland

  Sep 2, 20261h 2m

  Every AI startup wants to get closer to the customer.But what happens when getting closer turns your software company into a services business?In this episode of Verticals, Luke and Nic sit down with Quinn Litherland, founder and CEO of Revin, to explore one of the biggest shifts happening inside AI-native companies: the rise of forward-deployed teams.But there's a catch.Forward-deployed teams can become an excuse not to build scalable products. This episode will tell you how to avoid this trap. In this episode, they unpack:-Why forward-deployed teams are becoming critical to vertical AI-How to stop an AI startup from becoming a services company-Why the best forward-deployed hires look more like founders than engineers-Why customer success could become a revenue generator instead of a cost centerIf you're building vertical AI, rethinking your startup org chart, or trying to understand how forward-deployed teams actually work beyond the hype, this episode breaks down what the model looks like in practice... and where it can go badly wrong.️ 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 FOLLOW QUINN LITHERLANDLINKEDIN ➡️ https://www.linkedin.com/in/quinnlitherland FOLLOW LUKE SOPHINOSX ➡️ https://x.com/lukesophinosLINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ FOLLOW NIC POULOSX ➡️ https://x.com/picnoulosLINKEDIN ➡️ https://www.linkedin.com/in/npoulos/NEWSLETTER ➡️ https://insights.euclid.vc/ TIMESTAMPS:00:00 Intro01:24 Building AI automation for the home services industry05:05 Why the old SaaS org chart no longer works10:10 What does a forward-deployed employee actually do?18:04 The two traps of the forward-deployed model29:40 What should the ideal forward-deployed team look like?35:41 Can forward-deployed teams work with low-ACV customers?42:13 Why owning the workflow matters more than owning the data44:25 Is the software UI becoming irrelevant?53:18 The future: $500M companies run by five people58:58 The only three hires an AI-native startup needsTOPICS1. Forward-Deployed Teams 2. Vertical AI & Vertical SaaS 3. AI Agents 4. AI Startup Org Charts 5. The Future of Software

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  Verticals: A Weekly Biz Show

  The 5 AI Business Models That Could Replace SaaS | Yoni Rechtman

  Aug 26, 202656 min

  For 50 years, software companies sold tools. But customers never really wanted the tool. They wanted the job done. In this episode of Verticals, Nic sits down with Yoni Rechtman, Partner at Slow Ventures, to unpack why AI is breaking the traditional SaaS model and creating an opportunity that could be orders of magnitude larger. Historically, businesses spent only a fraction of their budgets on software. The rest went toward people, agencies, contractors, and services actually doing the work. But AI changes that equation: software can now execute the workflow itself, allowing startups to go after the service budget instead of just the software budget. Yoni lays out five emerging business models he believes could define the next generation of AI companies: using services to differentiate software, using software to differentiate services, AI-powered rollups, agent networks, and hardware that differentiates software. In this episode, they discuss: -Why customers want outcomes, not workflow software -How AI could expand traditional software markets by 30–100x -The difference between selling software and taking responsibility for the work -Why many vertical AI agents could struggle to build lasting moats If you're building in vertical AI, investing in software, or trying to understand what comes after SaaS, this episode is a framework for the business models that could define the next decade. ️ 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 FOLLOW YONI RECHTMAN LINKEDIN ➡️ https://www.linkedin.com/in/yrechtman X ➡️ https://x.com/yrechtman FOLLOW LUKE SOPHINOS X ➡️ https://x.com/lukesophinos LINKEDIN ➡️ https://www.linkedin.com/in/lukesophinos/ NEWSLETTER ➡️ https://www.newsletter.lukesophinos.com/ FOLLOW NIC POULOS X ➡️ https://x.com/picnoulos LINKEDIN ➡️ https://www.linkedin.com/in/npoulos/ NEWSLETTER ➡️ https://insights.euclid.vc/ TIMESTAMPS: 00:00 Why customers never really wanted software 06:27 The 5 business models that could replace SaaS 12:03 Why forward-deployed engineers are suddenly everywhere 16:40 The massive opportunity hiding in SMB labor budgets 17:35 How AI agents could create entirely new network effects 21:08 Why AI could make software markets 30-100x bigger 24:46 The problem with AI companies that just resell tokens 28:45 Software vs. services: who actually owns the outcome? 33:37 Why “better prompts” won't become a lasting AI moat 38:05 Is proprietary data really defensible anymore? 42:39 Why the software vs. services distinction still matters 49:18 The agent network business model explained 53:47 What happens when AI agents start spending money? TOPICS 1. Vertical SaaS 2. Vertical AI & Enterprise Software 3. AI Agents, OpenAI, Anthropic & the Future of SaaS 4. Small Business Finance

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