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Most AI can write code. Very little of it understands what that code does once it's running in production. That gap is where PlayerZero is building. Animesh Koratana started PlayerZero after his research at Stanford's DAWN Lab. His bet: AI for software should be collaborative, working alongside engineering, support, and QA from a shared model of how software engineering systems actually behave, not just a chatbot bolted onto a codebase. Today PlayerZero's AI production engineering platform works at companies like Zuora and Georgia-Pacific, delivering up to 80% fewer escaped defects. Animesh is bringing what he's learned about building that shared understanding to VSaaS Collective Live 2026 in San Francisco, October 21-22. If you're building AI-native and thinking about how agents and teams work from the same context, apply here before spots fill up: ordnl.link/9J1fdDy
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VSaaS Collective Live 2026 doesn't happen without our event partners bringing it to life. A huge thank you to the companies showing up for the vertical software community this year! Unit is our presenting sponsor. Tight is opening the event with the Kickoff Party at Pier 70 on October 21. Layer is hosting lunch. And we're joined by Check, Duda, Stripe, DialStack, Branch, Viaffinity, Forward, ADP, Happily and Gusto, all bringing tools that vertical software platforms rely on every day. We're grateful to have them in the room with us on October 21-22 in San Francisco. Apply to join us here: ordnl.link/PtYTAS3
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Eric Rea co-founded @PodiumHQ in 2014. Over the past few years, he’s led one of the more aggressive AI-native transformations in vertical software—reorienting the company around agents and expanding Podium from a communications point solution toward an AI operating system for local businesses. The bet: AI agents are eroding the traditional advantages of incumbent systems of record. As interfaces and features become easier to replicate, value shifts to the context, communications, payments, and infrastructure that agents run on. Today, Podium is doing more than $100M in AI ARR. He’s bringing that story—and what Podium learned from betting the product roadmap on agents—to VSaaS Collective Live 2026 in San Francisco on October 21–22. Space is now extremely limited. Apply to join us: ordnl.link/zHaqN6f
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Jeff Seibert took the harder path building @Digits: proprietary AI models trained in-house on $825 billion+ in business transaction data since 2018, years before the term Foundation Models became mainstream. Digits' models handle 95%+ of client transactions automatically, flagging outliers for human review. Jeff's argument: owning your model stack and training it on your own data is the durable competitive edge in a vertical. He's bringing that argument and a deep dive on building vertical models to VSaaS Collective Live 2026 in San Francisco on October 21-22. Apply to join us here: vsaaslive.com/?utm_source=li…
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Sam Trudo has scaled sales twice: nearly a decade at Toast, then leading revenue at EvenUp through 100%+ year-over-year growth, building the GTM engine across sales, enablement and partnerships. She's joining our GTM track at Collective Live 2026 to unpack how the sales motion changes when you go from selling SaaS to selling AI. Same buyer, different value story, different price. Most GTM teams haven't caught up. October 21-22 in San Francisco. If you're building AI and still selling it like SaaS, come hear Sam's take at Collective Live: ordnl.link/RnRbzqk
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Today, we're launching two new essays in our System of Action series. Investors have declared the application layer dead — Foundation Models chewing up Control Point incumbents and Native AI challengers alike as they move up the stack. @davelyuan's answer: we don't buy it. First up is 𝗣𝗮𝗿𝘁 𝟰: 𝗧𝗵𝗲 𝗖𝗮𝘀𝗲 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗔𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝗟𝗮𝘆𝗲𝗿. In it, Dave outlines why customers need an application layer to “do the work,” why the Foundation Models won't build it in most markets, and the size of the System of Action prize. Part 5 is the how: a framework for building the System of Action, with race plans for Control Point incumbents and Native AI challengers, and the war-gaming exercises we run with our portfolio. We're sharing Part 4 broadly. Part 5 stays limited to portfolio companies and operators — reply "Part 5" and we'll DM you.
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Catch 𝗣𝗮𝗿𝘁 𝟰: 𝗧𝗵𝗲 𝗖𝗮𝘀𝗲 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗔𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝗟𝗮𝘆𝗲𝗿 here: tidemarkcap.com/vskp-chapter…
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Adopting AI tools gets you 35% more throughput. The companies getting 5–10x did something else. Tidemark Partner, Rocky Gowni, and Tidemark Forward Deployed Engineer, Jaymin West, spent six months working hands-on with software companies on their engineering, product and design transformations. The finding was consistent: the gap has almost nothing to do with which tools they picked and everything to do with how they reorganized. A 35% gain isn't a transformation. It's a tool purchase. In our latest essay, the two lay out the four levels of EPD transformation, from engineers directing agents to a software factory that generates its own work. Most companies are stuck on the second. Read the full essay here: tidemarkcap.com/vskp-chapter…
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Garrett Lord co-founded @JoinHandshake in 2014 to connect job seekers with employers. Today, the platform reaches over 25 million job seekers, 1,600 US universities, and 1 million employers, from Fortune 500 companies to federal agencies to small businesses. Then the ground shifted with the era of AI. In 2025, Garrett launched Handshake AI, connecting domain experts on the Handshake network with leading AI labs to supply the human judgment frontier models need to train and improve.
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That evolution is one of the clearest examples we've seen of a vertical platform turning its proprietary network into a new system of value. The growth has been steep. Annualized revenue from AI training has since scaled from roughly $5 to 10 million a year ago to approaching $1 billion today. At Tidemark's Collective Live this October, Garrett joins us to share the Handshake story: how the company found an inflection point in the agentic age, and what it takes to act on one. October 21-22. San Francisco. Register to join us here: ordnl.link/agYsOep
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Insurance renewals involve a broker, a carrier, a policyholder and an account manager. Every touchpoint is a handoff. Every handoff is a delay. Jackson Fregeau and the team at Quandri built an agent that works across all of them. Most agents are single-actor: one workflow, one user. Quandri's is built for multi-stakeholder workflows — the agent has to understand state across parties who don't share a system, sequence tasks around dependencies it doesn’t control, and surface the right information to the right person at the right moment. Jackson joins us at Collective Live in October as part of our look at agent archetypes: what's actually scaling, how they're built and what it means for vertical SaaS. Collective Live is where the next generation of vertical platforms — traditional VSaaS and Native AI — come to win the agentic age.
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Join us. Oct. 21-22, San Francisco. vsaaslive.com/
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Ershad Jamil has launched a dozen add-on products and AI agents at @ServiceTitan and elsewhere. The rigorous pre-launch work, customer interviews, business cases, pricing validation, gives him confidence in the bet. It does not always tell him whether a launch will land. In our Fellows in Focus conversation, Ershad described the discipline he relies on instead: responding fast to the data once a product is in market. Pull back when something isn't working. Double down when it is. The leaders he sees fall behind are the ones slow to adjust after launch, not the ones who didn't validate enough before it. How do you decide when a slow start is worth pushing through versus pulling back to fix?
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Our first announced speaker for Collective Live 2026 is one of the few people genuinely rebuilding GTM for the agentic age. Kyle Norton has been building AI-native go-to-market at @Owner from the ground up, helping scale from $2M to $50M+ ARR along the way. Not AI-assisted or AI-enhanced, but rebuilt. They've already cut non-selling time by 25-30% per rep. The goal is 70-80% revenue-generating activity per person by letting AI handle the rest. Vertical SaaS companies that don't make this shift will lose to a team a tenth their size running a completely different motion. If you're a founder trying to figure out how to build a truly AI-native GTM motion, Kyle's breaking down the real build at Collective Live, October 21-22 in San Francisco. Apply to join us here: ordnl.link/P75joWf Follow along for the rest of the lineup — more speakers coming in the weeks ahead!
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Excited to have Andrew Walsh joining @dudaplatform's online vertical SaaS summit on May 27! The agenda is built around four of the questions operators are actively wrestling with right now: → How to beat the "SaaSpocalypse" → The agentic opportunity → AI monetization and agentic-ready packaging → AI visibility for SMBs Thanks to the Duda team for pulling together a lineup that's getting at the real shifts in vertical SaaS, from how AI is changing what platforms sell to how operators are repricing and repackaging for the agentic era. If you're rethinking pricing, packaging, or GTM, save your spot here: growth.duda.co/
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tidemark retweeted
I haven't been writing a lot. But after @Stripe asked me to speak at their SaaS Platform Leaders Summit alongside @eileenomara and @bdeeter, it turns out I had a lot to say.
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One Control Point. A swarm of agents coming for it. Public investors are saying it’s the end of vertical SaaS. SaaS stocks are down 40% on the thesis. @davelyuan's new essay is direct about how we see the SaaSpocalypse — and what separates the vertical SaaS Control Points and Native AI companies that survive from the ones that don't. It also sets up the conversation we're bringing to Collective Live in San Francisco on October 21-22, where 300 vertical SaaS and Native AI founders will be working through how to own the agentic age. If you're building through this transition, apply to join us at Collective Live: ordnl.link/06xmpGH Full essay linked here: ordnl.link/973RDZn
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When we asked Ershad Jamil what's changing right now that operators need to adapt to faster than they think, he didn't say AI. 👀 He said how companies are 𝘴𝘵𝘳𝘶𝘤𝘵𝘶𝘳𝘪𝘯𝘨 around AI. Watch the full clip below for what Ershad recommends operators do next. Curious where everyone lands: are you running one GM of AI, two, or none?
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Collective Live is back for a third year and applications are now open! What started as a half-day gathering in 2024 has grown into the annual event for the vertical SaaS community. More than 300 CEOs and founders from 17+ industries and four continents have come together to learn, connect, and build alongside each other. Past sessions have covered GTM flywheels, agentic AI, multi-product expansion, and the path to $1B in ARR, with leaders from Clio, Toast, Procore, ServiceTitan, CCC, Built, Moxie, Fora Travel (and more!) sharing how they actually did it. This October 21-22, we're going deeper on the biggest question in vertical SaaS: how to navigate the AI transition. Expect sessions on building and shipping agents, rebuilding engineering orgs into software factories, and rethinking pricing and GTM as the landscape shifts. Space will fill up quickly. Register to join: bit.ly/49nleRV
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