Tidemark

ServiceTitan went public at a multi-billion dollar valuation. They started as scheduling software for HVAC contractors. The gap between those two points is their multi-product strategy. They didn't try to be everything at once. They sequenced deliberately based on what customers were already trying to solve. The pattern: prove you can own the workflow, then expand into products that make the core platform stickier, become the system of record. Here's how ServiceTitan sequenced its way to a platform. 👉 Dive into ServiceTitan's framework for prioritizing expansion opportunities here: ordnl.link/FinxmU4

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.

Sarah Connor didn't know she was going to become a badass. She just accepted the reality of what was coming for her and acted. That's the framing David Yuan uses in System of Action Part 3. You're the CEO of an incumbent vertical SaaS Control Point. You've scaled locations, gone multi-product, maybe extended through the value chain. You've done everything right. Now Native AI is coming for you. The good news: Control Points have an unfair structural advantage. Workflow gravity, data gravity, trusted relationships — all of it remains intact when a new technology arrives. That's the foundation for what comes next. The early results from Control Points that have moved: 2–5x uplift in ARPU without cannibalization. In some cases 10x, when agents take on work that was previously outsourced. The full 8-step playbook for how incumbents fight back is in the slides above. Get access to Part 3 here: ordnl.link/0Y6GKNE

Congrats to the Toast team on being named to Fast Company's Most Innovative Companies of 2026 list! Toast has been relentlessly focused on empowering restaurant operators since the beginning. Fast Company's recognition is a reflection of that consistency.

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.

Some vertical SaaS companies are earning 10x the take rates of their peers. The pattern behind it has a name: Formation and Access. David Yuan makes the case it may be one of the most disruptive Control Point patterns since embedded payments. Formation means helping entrepreneurs actually start a business: breaking down the regulatory, operational, and competitive barriers that stop people from getting off the ground. Access means solving the key constraint that keeps a newly formed business from competing with scaled incumbents — whether that's insurance payor designation, supplier access, or regulatory clearance. The companies doing both well are creating businesses that wouldn't exist without them. The revenue follows from that, and so does the relationship. The catch: 10x take rates don't sustain themselves without deliberate work. Graduation risk is real, and high margins attract competition. Swipe through for how the best Formation and Access platforms build defensibility that compounds at scale. Request access to the full framework here: ordnl.link/hMfjyFr

ServiceTitan grew ACVs from $15K to $50K. Nobody predicted that when Ershad Jamil joined as employee # 49. Ershad is a Tidemark Fellow and former Chief Growth Officer at ServiceTitan, where he helped build some of the company's most successful product lines, including Payments and Marketing Pro. When early-stage founders come to him for advice, the most common objection they hear from investors is always the same: the TAM is too small. Ershad thinks that math is broken. The standard TAM calculation looks at today's customer count, today's ACVs, and today's competitive landscape. It treats the market as a fixed number. But the best vertical SaaS companies don't inherit their TAM. They build it. New products, upmarket expansion, and AI-powered workflows can push a $5K ACV to $30K or $40K over time. That was the ServiceTitan story, and Ershad sees the same setup happening across SMB verticals right now. His conviction test for founders: can you capture 2-3% of your customer's revenue over time by stacking enough value across their workflow? If the answer is yes, the TAM math everyone is running today is irrelevant. This is Fellows in Focus, a new Tidemark series spotlighting operator wisdom from our Fellows network. Follow our page to make sure you don't miss the next one, and drop your questions for our fellows below. 

Every vertical has a version of the same person. At a restaurant, it's whoever answers the phone during the lunch rush. At a law firm, it's the junior associate stuck chasing tiny retainer clients. At a dental practice, it's whoever handles insurance verification calls. We call this person Cousin Richie. The internal staffer, the outsourced agency, or the offshore team handling high-priority, high-hassle work that requires coordination across systems, people, and external stakeholders. Sometimes Cousin Richie is a real person on staff. Sometimes it's an agency billing $400 an hour. And sometimes, the work just doesn't get done at all. AI runs circles around Cousin Richie. It works 24/7, speaks 40 languages, and never loses its focus. For Native AI companies, this is the wedge into the business owner's budget. Solve the problem that keeps them up at night, earn their trust, and build from there. The full Part 2 of the System of Action series breaks down exactly how: ordnl.link/0eqLNac

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: ordnl.link/N17fl14

A provider, a lawyer, and a contractor try your AI feature. 👉 Each one has a different reason not to trust it. The provider worries about patient safety. A wrong recommendation could mean a misdiagnosis. Regulatory requirements like HIPAA create barriers that horizontal AI tools weren't designed to navigate. The lawyer worries about confidentiality. Client privilege means data can't leak across cases. A hallucinated citation in a brief could mean sanctions. The contractor worries about liability. An AI that suggests the wrong material spec doesn't create a bad user experience. It creates a structural problem that takes years to surface. John Foreman, CPO at Clio, put it well on stage at Collective Live: without proprietary context, foundation models are "eloquent idiots." Clio made a major legal content acquisition specifically so that every AI-generated claim or citation could anchor to sourceable authority. That's what it takes to earn trust in a vertical where getting it wrong has real consequences for the client. The VSaaS companies gaining traction with AI are designing for these trust dynamics from the ground up, vertical by vertical. What does the trust barrier look like in your vertical?