Head of Product

About Property Pilot

Real Estate is the largest asset class in the United States — over $85 trillion in total value, with more than $2 trillion changing hands every year and roughly $100 billion paid in commissions to 1.5 million licensed agents across 100,000+ brokerage firms — and yet it remains one of the most fragmented, data-starved, and inefficient industries in the country. The property data that powers every deal is scattered across thousands of county assessor offices, MLS systems, and legacy enterprise providers — clunky interfaces, stale records, and six-figure price tags.

Property Pilot is changing that. We're an early-stage, AI-powered real estate platform unifying 170+ million tax and parcel records nationwide — ownership, assessments, comparable sales, mortgage and foreclosure filings — into a single, mobile-first experience built for the investors who source, underwrite, and close deals every day. On top of that public-record foundation, we're building a crowdsourced layer of the documents that actually live the deal — architectural plans, surveys, leases, appraisals, inspections — contributed by the professionals who generate them and made searchable across the network.

We're fusing public records, crowdsourced documents, market signals, and AI-driven workflows into a product that puts professional-grade intelligence in an investor's pocket — not buried in a six-figure enterprise contract.

Behind the product is a hard set of product problems: figuring out which investor segment to win first, what to price, what to build vs. partner for, and how to turn a fragmented data corpus into workflows that meaningfully change how a real estate professional researches, underwrites, and closes a deal. Backed by an experienced SaaS founder and a seasoned product, engineering, and design team, growth at Property Pilot today is about getting the right users in the door, learning from real usage, and iterating fast.

It's a rare chance to help define a category at the intersection of AI, data, and the largest asset class in the country.

As Head of Product, you are Property Pilot's most senior product voice. You own product strategy, the multi-year roadmap, customer discovery, pricing and packaging, product analytics, and the day-to-day Product Owner work that keeps engineering shipping. You translate our 9-Phase business roadmap into a sequenced product plan, author the PRDs that drive engineering execution, run the discovery sprints that test our assumptions, and own how Claude is embedded across the product function.

This is a single combined seat by design – Property Pilot needs one person who can set the strategic direction and live inside the backlog.

Set Product Strategy and Sequence the Roadmap. Own a multi-year product strategy tied to our 9-Phase business roadmap — including phase sequencing, the features/discovery/platform mix each cycle, the build‑vs‑partner calls, and present the major roadmap defensive to Executive Leadership team.

Author the PRDs and Own the SDLC Partnership. Author PRDs for every project using the mandatory 9-section template from the Property Pilot SDLC Playbook; leverage Claude to draft initial sections, generate user stories, and stress‑test acceptance criteria for completeness. Coordinate the PRD Approved stage gate (3‑person sign‑off with Lead Engineer and Designer); lead Pass 1 Refinement sessions; make scope and priority trade‑off decisions within each sprint;

shield the team from mid‑sprint scope changes. Partner with Engineering leadership on the SDLC end‑to‑end — backlog refinement, Definition of Ready, sprint planning, sprint review, Definition of Done, release gates — owning the what and the why while respecting Engineering's call on the how.

Run Customer Discovery as a Discipline. Personally interview real estate investors, lenders, and agents on a recurring cadence; synthesize qualitative insights into roadmap decisions; build the discovery rituals the team trusts. Define, monitor, and act on product KPIs using Mixpanel — engagement funnels, search behavior, feature adoption, credit consumption, monetization…