Chief Technology Officer

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 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.

The Role

As CTO, you are PropertyPilot’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 DevOps Engineer, govern our SDLC Playbook, and own how Claude is embedded across every department.

What You’ll Do

Set Technology Strategy and Architecture.

• 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.

Build the Engineering Organization.

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

Own Organization-wide AI Strategy.

• 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, GitHub, Cursor, and future providers).

Own Security, Risk, and Executive Communication.

• 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.

A Role with Its Own AI Counterpart

Every senior role at PropertyPilot owns a Claude-powered digital counterpart. As CTO, you’ll build and maintain the Technology Strategy Agent — an executive-level synthesizer that drafts board-ready updates, benchmarks DORA metrics, surfaces security and compliance drift, and produces strategic analyses that would otherwise need a full engineering-operations team. You’re accountable for its accuracy, discretion, and alignment with our strategic positioning, and for validating every board- and investor-facing output it produces.

Required Skills \& Experience

• 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 Have

• 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.

Who You Are

• You pick the simplest solution that meets the need and revisit it when the data or the business outgrows it.
• Quality-obsessed. You treat data quality as a first-class feature. Bad data is a bug, and you hunt it down at the source.
• 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.
• 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.
• Competitive compensation. Salary, equity and benefits commensurate with experience/stage of the company.

PropertyPilot is an Equal Opportunity Employer.