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?
@RilletHQ is one of the few AI companies building toward full replacement of the Control Point — rebuilding the accounting system of record from the ground up, with the product and onboarding engineered to support that strategy.
That's why @nicckopp, CEO of Rillet, is speaking at Collective Live 2026. Nic will share the Rillet story: what it actually takes to displace an entrenched system of record rather than sit alongside it.
Register here: https://t.co/rKV7NlRauZ
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: https://t.co/x9g4VZhD6H
Follow along for the rest of the lineup — more speakers coming in the weeks ahead!
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: https://t.co/plqqHJCbHA
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.
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: https://t.co/2kWhLQ7dW2
Full essay linked here: https://t.co/oVszsXc6kR
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?
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: https://t.co/tVWVl0dEqG
The hardest operating lesson Kevin Hamilton learned took years to fully trust. And it still runs counter to most founders' instincts.
At two companies built for specific verticals, the GTM discipline was the same. Limit the leads an SDR works. Limit the accounts in an AE's territory. Conversion rates go up, not down.
In the second episode of Fellows in Focus, Kevin shares the operating lessons that shaped how he leads, and how he thinks about go-to-market focus with founders building now. Hit follow so you don't miss more from this conversation.
Hiring a Chief Growth Officer is one of the harder searches a VSaaS company will make.
Ershad Jamil spent years at @ServiceTitan building Payments and new business lines from the ground up — and when he thinks about what he'd look for in that role today, it comes down to one thing: someone entrepreneurial enough to run a business line from zero, with the range to own a P&L, navigate BD, and still get into the weeds when the work requires it.
Ershad breaks down exactly what he looks for in this episode of Fellows in Focus, a new series where Tidemark Fellows share the operator wisdom they wish they'd had earlier. More coming soon.
Collective Live is coming back to San Francisco October 21-22!
We started this event to bring together leaders of emerging vSaaS companies for a day of in-person discussion and learning with legendary operators, without the pressure of other investors in the room. That's what makes this day different.
Last year, over 200 vSaaS CEOs from four continents spent a day working through the strategic questions that define this market: how AI reshapes control points, when to go multi-product, how PE consolidation changes your competitive landscape. The room represented $4B+ in combined ARR across 17+ industries, and the conversations are still shaping how operators run their companies months later.
Year 3. Same mission. Capacity is limited, so sign up now to be the first to get notified when registration opens this Spring!
If you're a Vertical SaaS CEO or founder, we hope to see you in October: https://t.co/7vkq3D5aRD
Every time we get founders from the same vertical together, the knowledge sharing is on another level.
This morning in New York, we brought legal tech founders together with Ronnie Gurion, COO at @GoClio, over breakfast. Three threads kept coming back:
Third, how AI adoption is really playing out. Founders are seeing workflow-specific RFPs instead of broad AI mandates, heavy onboarding and professional services requirements, and a lot of organizational confusion: FOMO, privilege concerns, evolving AI policies. The roles of IT, legal ops, and even law firms themselves are shifting as AI reshapes who advises on what.
How do you change a fragmented industry like construction? At Collective Live, @ChaseGilbert , CEO of @builttechnology, shared what it really takes: start with the flow of money and build outward from the true leverage point.
Built began with lenders, not contractors or owners, and spent years building a system that became the industry’s shared ledger. Today, the platform connects over 300 financial institutions and more than $300B in active real estate. Every new stakeholder was added only after the foundation was proven.
Chase’s message for founders is clear. Workflows create value, but coordination is the moat. When you become the shared truth in a spreadsheet-ridden, multi-party value chain, you change how an industry moves and resolve the pain and waste that hold it back.
Get the full recap from Chase Gilbert's #CollectiveLive2025 session here: https://t.co/ierQU3NLt2
Dave Yuan the case at Collective Live that private equity isn't a background influence in Vertical SaaS anymore. It's a customer segment with its own buying behaviors, incentives, and internal politics.
Once PE starts consolidating a vertical, the buyer landscape shifts. Companies that treat PE as a real segment outperform those that treat it as happenstance.
Dave broke down how to actually sell into PE firms, including the three personas you need to understand and the product opportunities most founders miss. He also walked through how companies like SiteMinder and Carbon turned their data into deal-sourcing intelligence that PE firms now depend on.
If PE is consolidating your vertical, this playbook is worth your time. Dive into the #CollectiveLive2025 recap here: https://t.co/l95fainO9v
Only 41% of Vertical SaaS companies in our 2025 Benchmark Report are still single-product.
Nearly 60% have already made the leap to multi-product. If you’ve expanded, what was the tipping point for your team? If you’re still single-product, what signals are you watching before making the move?
The Platform Journey continues! 🚀
This week, host Avanish Sahai sits down with Drew Sechrist , CEO of Connect The Dots (CTD). An early Salesforce veteran who joined when the company had zero paying customers and helped scale it to over $1 billion in ARR.
Catch the full conversation here: https://t.co/rjFMANAAJ4