This made money three ways. New revenue: benefit upgrades went 0% → 18% in pilot → 23% at GA — a brand-new ancillary stream for Second Nature and the property manager, on every lease. Acquisition and retention: Second Nature owning compliance de-risks the PMC — that wins deals and keeps them. Scale: the platform removed the linear-headcount ceiling, so growth stopped hiring its way forward. The rest of this page is how.
For context: I joined as the company's third product hire and was promoted to Principal PM within seven months. The industry standard for lease execution was 48 to 72 hours, and nobody thought that was strange.
The most valuable discovery channel was uncomfortable: an enterprise pilot where the customer's CEO joined every weekly call, asking for SSO, permissions, and management features the MVP didn't have. Instead of saying no, I mapped every request to his own KPIs and showed him his two launch markets ran a flat org that didn't need permissions yet. He agreed with the "not right now" — repeatedly — and the account became a reference.
Underneath that, funnel analytics did the quiet work. I built the company's analytics foundation from scratch — Amplitude, Looker, Chameleon — because you can't shorten a funnel you can't see.
Rules as configuration, not code. Every property type, operational rule, and jurisdiction was becoming custom engineering. I led a conditional-logic infrastructure that turned rules into config — adoption rose 30%, and each new market stopped costing engineering time.
The plumbing decision. Lease rendering kept failing intermittently and was treated as a support problem. I traced it to DOCX generation and made the case to migrate the pipeline to PDF — unglamorous infra work competing with shiny roadmap items. Result: zero rendering failures across the first 100 transactions, load times under two seconds, CSAT from 6 to 9.
Seven weeks to AppFolio. A strategic enterprise deal hinged on an integration with a fixed deadline and data sync across four systems. I cut scope to the day-one paths, negotiated the cut list with the customer directly, and had integration testing running by week two. Shipped on time.
The platform reached 75,000+ units and contributed $10M+ in contracted ARR. Lease execution went from the industry's 48–72 hours to 85% same-day. And because the upgrade offer lives inside the moment residents are already committed, conversion climbed from 0% to 18% in pilot to 23% at GA — roughly $15 of found revenue per lease, improving the whole way under active management.