Chief Technology Officer

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 technical problem: ingesting and reconciling messy, heterogeneous public data at national scale, layering on a crowdsourced corpus of unstructured documents, and making all of it usable through AI‑native workflows that meaningfully change how an investor 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 CTO, you are Property Pilot’s most senior technical leader and a member of the executive team. You own technology strategy, the engineering organization, our security and compliance posture, and the AI‑native culture that differentiates us. You translate our 9‑Phase business roadmap into a multi‑year technology roadmap, set architectural direction, own the engineering budget, and represent engineering to the board, investors, and partners.

You directly manage the Lead Engineer and Dev Ops Engineer, govern our SDLC Playbook, and own how Claude is embedded across every department.

• Own a multi‑year technology strategy tied to our 9‑Phase roadmap — including the Platform roadmap, direction for our differentiated capabilities (Parcel Service API, Munin NL search, Martin VTS, the Medallion data architecture, the Phase 7 auction marketplace), major ADRs and build‑vs‑buy calls, the features/platform/debt mix each cycle.

• Own org design, headcount planning, senior hiring, and compensation philosophy with the CEO and Head of HR; directly manage the Lead Engineer and Dev Ops Engineer; govern the SDLC Playbook; and partner with the Product Owner on roadmap and capacity.

• Own how Claude is embedded across every department, govern our Digital Counterpart Model so every role‑specific agent is delivering measurable value, track AI ROI monthly and run quarterly AI Effectiveness Reviews, and approve AI tooling spend and vendor contracts (Anthropic, Git Hub, Cursor, and future providers).

• Own our security posture and compliance programs (SOC 2 Type 2, GDPR, state privacy), the technical risk register, quarterly board updates on DORA metrics and AI adoption ROI, and the full engineering budget across cloud, tooling, vendors, AI spend, and headcount.

Every senior role at Property Pilot owns a Claude‑powered digital counterpart. As CTO, you’ll build and…