Head of Operations

PermitFlow is redefining how America builds. We’re an applied AI company serving the nation’s builders, tackling one of the largest information challenges in the economy: understanding what can be built, where, and how. Our AI agent workforce helps the fastest-growing construction companies navigate everything from permitting and licensing to inspections and project closeouts – accelerating housing, clean-energy, and infrastructure development across the country. Despite being a $1.6T industry, construction still suffers from massive delays, wasted capital, and lost opportunity. PermitFlow has already delivered unprecedented speed, accuracy, and visibility to over $20B in development, helping contractors reduce compliance time, de-risk projects, and scale with confidence. As the U.S. enters a new capex supercycle across data centers, factories, housing, and renewables, joining PermitFlow means building the AI infrastructure at the core of every construction project driving the next wave of reindustrialization. We’ve raised over $90M, most recently completing our Series B, https://www.permitflow.com/blog/permitflow-series-b from top-tier investors including Accel, Kleiner Perkins https://www.linkedin.com/feed/update/urn:li:activity:7401703305569275904/, Initialized, Y Combinator, Felicis, and Altos Ventures, with backing from leaders at OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. ROLE OVERVIEW We’re looking for a Head of Operations to lead and scale the operational engine behind PermitFlow. This role will oversee a large, multi-layered operations organization responsible for delivering permitting outcomes for customers, supporting new customer pilots, and ensuring excellent service that drives retention and growth. The Head of Operations will work closely with Sales, Customer Success, and Product, Engineering, and Design to continuously improve operational workflows and help translate operational insights into product and AI-driven automation.. WHAT YOU’LL DO - Lead and scale PermitFlow’s core operations organization. - Manage a team of Operations Managers and Operations Leads - Partner with Sales and Customer Success to onboard prospective and new customers and help convert them into long-term partnerships. - Own customer operations, ensuring customers receive reliable, high-quality service that drives retention and expansion. - Work closely with Product and Engineering to identify opportunities for AI agents and workflows - Build systems, metrics, and processes that enable the operations team to scale efficiently as the company grows. WHAT WE’RE LOOKING FOR - 7–12+ years of experience in operations, with at least 3–4 years in a senior leadership role managing managers and large teams - Strong operator who can balance strategy, systems design, and execution. - Experience scaling operational processes in a high-growth environment. - Comfortable working cross-functionally with product and engineering teams. - Proven track record scaling operations in a high-growth startup - Experience managing teams at meaningful scale (100+ people) - Strong commercial instincts you understand how operations connects to revenue, retention, and growth - Data-driven decision maker who can define the right metrics, interpret them, and act on them - Experience working alongside or within a product/engineering organization; comfort with technology and AI - Excellent communicator and cross-functional partner; you can hold your own in a room with Sales, Engineering, Finance, and the executive team - Experience in construction, real estate, permitting, or government services is a plus but not required Nice to have - Experience implementing automation or AI - Exposure to construction, permitting, or real estate development. WHY THIS ROLE MATTERS Operations is at the center of how PermitFlow delivers value to customers. This role will help build the systems that power thousands of permitting workflows while helping build scalable so