Head of People at PermitFlow (W22) $200K - $300K TurboTax for Construction Permitting New York City, NY Full-time US citizen/visa only 11+ years About PermitFlow PermitFlow is redefining how America builds. Pre-construction remains one of the most broken and manual parts of the $1.6T construction industry, causing massive delays, wasted capital, and lost opportunity across the built world. Our AI workforce delivers unprecedented speed, accuracy, and visibility to pre-construction — accelerating housing development, enabling clean-energy projects, and driving economic growth in communities nationwide. To date, we’ve powered over $20B in real estate development, helping builders and contractors move faster, reduce risk, and scale with confidence. We’re entering hypergrowth with clear product-market fit and a world-class team from top AI and construction companies. We’ve raised over $36.5M from Kleiner Perkins, Initialized Capital, Y Combinator, Felicis Ventures, and Altos Ventures, alongside backers from OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. We are on a mission is to modernize how the built world operates. About the role 🚀 About PermitFlow PermitFlow is redefining how America builds. Pre-construction remains one of the most broken and manual parts of the $1.6T construction industry, causing massive delays, wasted capital, and lost opportunity across the built world. Our AI workforce delivers unprecedented speed, accuracy, and visibility to pre-construction — accelerating housing development, enabling clean-energy projects, and driving economic growth in communities nationwide. To date, we’ve powered over $20B in real estate development, helping builders and contractors move faster, reduce risk, and scale with confidence. We’re entering hypergrowth with clear product-market fit and a world-class team from top AI and construction companies. We’ve raised over $36.5M from Kleiner Perkins, Initialized Capital, Y Combinator, Felicis Ventures, and Altos Ventures, alongside backers from OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. We are on a mission is to modernize how the built world operates. Our HQ is in New York City with a hybrid schedule (3 in-office days per week). We prefer NYC-based candidates or those open to relocation. ROLE OVERVIEW As Head of People, you’ll design and run the systems that power how we hire, onboard, grow, and support every member of the team. You’ll transform our people function into a strategic engine - one that connects culture, performance, and business outcomes. From architecting our HR tech stack to shaping how managers lead and teams thrive, you’ll build the infrastructure that keeps our company strong as we scale. What You’ll Do Build and lead a high-performing People Ops operating cadence , setting priorities and partnering cross-functionally with Finance, Legal, and Department Heads to ensure operational excellence. Serve as the architect and administrator of our People systems (Rippling) - maintaining data integrity, optimizing automations, and integrating tools that streamline HR, payroll, and compliance workflows. Drive performance, compensation, and leveling frameworks , ensuring alignment to business goals, retention, and career growth. Advise leadership on org design, headcount planning, and change management , balancing business velocity with a consistent and compliant employee experience. Champion employee experience as a strategic advantage - creating systems and resources that make information transparent, empower self-service, and build trust across the organization. Serve as a thought partner to the CEO and leadership team on People strategy, culture, and long-term organizational design. What We’re Looking For 8–10+ years of People/HR experience , including time in a high-growth or startup environment where you’ve built and scaled programs from the ground up. Proven ability to own and improve People systems and processes end-to-end , from data accuracy to workflow automation. Strong strategic instincts paired with hands-on operational rigor - you can design frameworks and execute them with speed and precision. Exceptional communication and influencing skills - trusted by executives, respected by peers, and empathetic with employees. Adaptable and nimble – skilled at building scalable processes while seamlessly flexing with evolving business needs. Highly organized, detail-oriented, and proactive - you see around corners and drive initiatives forward without waiting for direction. Deep understanding of employment law, compliance, and best practices across multiple states (PEO experience a plus). Based in NYC , with the ability to work in-office M/W/F alongside the leadership team. 💙 Benefits: 📈 Equity packages 💰 Competitive Salary 🩺 100% Paid health, dental & vision coverage 💻 Company issued laptop. 🎧 Home office & equipment stipend 🍽️ Lunch & Dinner provided via UberEats w/ a fully stocked kitchen 🚍 Commuter benefits 🎤 Team building events 🌴 Unlimited PTO