About PropertyPilot
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.
PropertyPilot 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 PropertyPilot 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.
The Role
As Head of Product, you are PropertyPilot'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 – PropertyPilot needs one person who can set the strategic direction and live inside the backlog.
Position Responsibilities
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 PropertyPilot 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 conversion — and use those signals (together with the qualitative discovery work) to inform backlog priorities. Maintain Mixpanel dashboards for sprint reviews and stakeholder updates; use analytics data to validate acceptance of shipped features and measure success metrics defined in PRDs.
Own Pricing, Packaging, and Monetization Strategy. Own the pricing tier design and credit‑pack monetization model; coordinate with the CEO on enterprise contract structures; monitor Stripe Dashboard for subscription tier performance, credit pack purchase trends, and revenue metrics; iterate on pricing as discovery and analytics reveal what's working.
Own Organization‑wide Product AI Strategy and the Product Analyst Agent. Own how Claude is embedded across the product function — PRD drafting, user‑story generation, acceptance criteria refinement, competitive analysis, customer‑feedback synthesis, release notes, stakeholder communications. Build and maintain a Product Analyst Agent — a Claude‑powered digital counterpart that handles routine analytical and generative product work so you can focus on strategy, stakeholder alignment, and decision‑making. You're accountable for its accuracy, discretion, context, and ongoing improvement.
Champion Product externally with Customers and Investors. Be the product face to customers, partners, and prospective investors; co‑author quarterly board materials on product KPIs, AI adoption ROI, and discovery learnings; defend the roadmap publicly and absorb the feedback honestly.
Every senior role at PropertyPilot owns a Claude‑powered digital counterpart. As Senior Product Owner, you'll build and maintain the Product Analyst Agent — an always‑available product intelligence assistant that drafts PRD sections from project briefs, generates user stories with acceptance criteria, synthesizes Mixpanel data into weekly product‑insight summaries, prepares sprint review talking points from Linear cycle data, generates release notes, and surfaces backlog priority recommendations based on analytics trends. The agent integrates with Linear, Notion, Mixpanel, HubSpot, Stripe Dashboard data, and Slack via MCP. You're accountable for its accuracy, discretion, context window, prompt library, tool integrations, and continuous improvement based on output quality and team feedback.
Required Skills & Experience
- 8+ years of product management experience, with at least one prior tour as the senior‑most product voice in a startup of fewer than 100 people.
- Demonstrated PRD authorship at a level that drove real engineering execution — willing to share a recent example.
- Track record owning a roadmap end‑to‑end and defending it against a CEO, a board, or a senior sales leader.
- Hands‑on customer discovery experience — personally running user interviews, synthesizing insights, and changing roadmap decisions because of what you heard.
- Hands‑on pricing and packaging experience — owning a tier structure, a credit model, or an enterprise contract design and living with the results.
- Hands‑on product analytics fluency — Mixpanel, Amplitude, or equivalent; defining events, building funnels, interpreting retention.
- Demonstrated AI‑native product transformation — using LLM tools across PRD authoring, discovery synthesis, and analytics with measurable velocity and quality outcomes — plus the ability to build executive‑level AI agents that synthesize, not just automate.
- Strong understanding of Scrum ceremonies, backlog refinement, Definition of Ready enforcement, and the boundary between product (the what) and engineering (the how).
- Excellent executive communication — board memos, investor updates, customer narratives, and roadmap defenses explained to non‑technical and technical audiences alike.
Nice to Have
- Proptech, real estate data, geospatial, SaaS data products, or marketplace experience.
- Prior founding‑team experience or "PM #1 at a Series A" experience.
- Experience with credit‑based or subscription monetization models in regulated industries.
- Experience taking a VC‑ or PE‑backed company through a successful exit (acquisition, IPO, or major liquidity event), including product‑side due diligence.
- Certified Scrum Product Owner (CSPO) or equivalent certification.
Who You Are
Customer‑obsessed. You live in the customer's world. Every backlog decision starts with "what does this unlock for the user?" and you're never more than a conversation away from real feedback.
Quality‑obsessed. You treat the PRD as a first‑class artifact. Vague acceptance criteria are a bug, and you hunt them down before code gets written.
Decisive. You make priority calls with incomplete information, own the trade‑offs, and don't hide behind consensus. When you're wrong, you adjust fast.
Resilient. Startups are hard. Priorities shift, requirements evolve, and ambiguity is constant. You don't just tolerate this — you operate well within it.
Direct and low‑ego. You give and receive feedback openly. You care more about the right answer than being right. You respect engineering's call on architecture and sprint sequencing without litigating it.
Self‑directed. You don't wait to be told what to do. You see problems, propose solutions, and execute.
Why PropertyPilot
Massive market, real problem. The U.S. real estate data ecosystem is fragmented and outdated. We're building the infrastructure layer to fix it.
Early‑stage impact. Your work will directly shape the product, the roadmap, and the company's trajectory.
Strong foundation. Experienced SaaS founder, proven team, and a clear product vision — not a science experiment.
AI‑native from day zero. Not "we're adopting AI" — the company is organized around it, and product is where the leverage compounds.
Competitive compensation. Salary, equity, and benefits commensurate with experience and the stage of the company.
PropertyPilot is an Equal Opportunity Employer.
AI disclosure: As part of our recruiting process, PropertyPilot may use AI‑assisted tools to help screen, review, and organize applications, as well as to support scheduling and communication. These tools assist our team and all final hiring decisions are made by humans. We work to ensure these tools are used fairly and without unlawful bias. If you have questions about how AI is used in your application, would like to request a reasonable accommodation or an alternative review process, please contact us at (848) 321‑5588.
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