Chief Technology Officer
16 hours ago
Manasquan
Job DescriptionSalary: 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 PropertyPilots 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 Youll Do Set Technology Strategy and Architecture. • 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, youll 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. Youre 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 (1030 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 dont just tolerate thisyou 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 dont 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. Were building the infrastructure layer to fix it., • Early-stage impact.Your work will directly shape the product, the roadmap, and the companys trajectory., • Strong foundation.Experienced SaaS founder, proven team, and a clear product visionnot a science experiment., • Competitive compensation.Salary, equity and benefits commensurate with experience/stage of the company. PropertyPilot is an Equal Opportunity Employer.