Chief Technology Officer

PropertyPilot•Wall Township, NJ

About The Position

PropertyPilot is 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 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.

Requirements

12+ years in software engineering, with 5+ as CTO, VP Engineering, or an equivalent executive.
Track record scaling engineering orgs from early-stage (10–30 engineers) through growth-stage.
Deep, current expertise across modern mobile (Flutter or native), web, AWS, data engineering, and geospatial or search systems.
Demonstrated AI-native engineering transformation — embedding LLM tools across workflows with measurable velocity and quality outcomes — plus the ability to build executive-level AI agents that synthesize, not just automate.
Security and compliance ownership (SOC 2, GDPR, HIPAA, or similar) and budget ownership at meaningful scale.
Strong executive communication — board memos, investor updates, and technical trade-offs explained to non-technical audiences.
Experience hiring senior engineering leaders and setting compensation philosophy with HR.

Nice To Haves

Proptech, real estate data, geospatial, SaaS data products, or marketplace experience.
Prior founding-team or bootstrapped, small-team experience.
Experience taking a VC or PE-backed company through a successful exit (acquisition, IPO, or major liquidity event), including leading technical due diligence.