Category: The Long View

Most companies treat pricing like a moment: a debate that resurfaces when growth slows or a competitor forces the issue. The better operators treat it as a system, not a periodic fix. Drawing on experience at Opower, Benefitfocus, and Toast, this playbook lays out the sequencing, governance, packaging discipline, usage-based leverage, and infrastructure required to turn pricing and packaging into a compounding growth engine for Vertical SaaS.

At the 2025 VSaaS Collective Live on November 5, Chase Gilbert walked through what it actually takes to change a fragmented industry like construction. His session made a blunt case for starting with the real leverage point — the flow of money — and building outward from there. What followed wasn’t theory, but the eight-year process behind turning construction finance into a functioning industry ledger.

Private equity is no longer a side influence in VSaaS, but a primary customer shaping how products spread and markets consolidate. At VSaaS Collective Live 2025, Dave Yuan walked through how to approach this segment.

At Tidemark’s 2025 VSaaS Collective Live, Kevin Hamilton, Tidemark Operating Partner & Former CMO, shared his framework for building a scalable GTM motion.

At Collective Live 2025, Marc Fredman broke down CCC’s forty-year climb: from a point solution to the operating fabric of the auto-insurance economy

At Tidemark’s 2025 VSaaS Collective Live, CEOs from Revin, Sewer AI, and HiMarley shared lessons on how to effectively sell AI to the enterprise

At VSaaS Collective Live on November 5, John Foreman delivered the talk that felt closest to the operator’s nerve. He skipped the interface demos and went straight at the real failure mode in AI: teams shipping features that don’t eliminate any work. Foreman’s session reframed the whole conversation from “what can AI do?” to “what toil can we erase?”

For vertical SaaS companies, PE consolidation creates both challenges and opportunities. This playbook is designed to provide actionable approaches that vertical SaaS leaders can implement across their organizations.

Tidemark Venture Partner and former CMO at Toast, Kevin Hamilton, shares the five components that help founders stop managing tension between teams — and start scaling momentum across them.

Tidemark Venture Partner and former CMO at Toast, Kevin Hamilton, shares insights from Toast’s journey from $40M to $1.2B in ARR