Head of Product 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, from top-tier investors including Accel, Kleiner Perkins, Initialized, Y Combinator, Felicis, and Altos Ventures, with backing from leaders at OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber.

• Construction is one of the largest industries in the world - and one of the most operationally fragmented.

• Before anything gets built, projects must move through permitting and pre-construction workflows spread across ~20,000 jurisdictions, each with different rules, systems, and processes.

• The result is a massive bottleneck slowing down housing and infrastructure across the country.

• PermitFlow is rebuilding this layer from the ground up - using modern software and AI systems to automate and orchestrate permitting end-to-end.

• We are still early. The product surface area is expanding rapidly, the workflows are deeply complex, and the opportunity to shape how this industry operates is enormous.

• This is one of those rare moments where product decisions directly influence how the physical world gets built.

Location

• Our HQ is in New York City with a hybrid schedule (Monday, Wednesday and Friday in-office). We prefer NYC-based candidates or those open to relocation.

Role Overview

• We are looking for an experienced and hands-on Head of Product Operations to build and lead PermitFlow’s Product Operations function.

• In this role, you will define how our Product organization plans, operates, launches, and measures its work. You will evolve our Product Operations capabilities from a small team into a well-staffed, strategic organization that partners closely with Product, Engineering, Design, Operations, and the founding team to help the company execute more effectively.

• You’ll be responsible for hiring and developing a team of Product Operations Managers, defining the company’s Product operating system and quality standards, and building the systems and processes that enable great product execution at scale.

• This is a player-coach leadership role that requires exceptional operational judgment, strong product instincts, and the ability to operate both strategically and hands-on in a fast-paced startup environment.

What You’ll Do

• Build and lead PermitFlow’s Product Operations organization, evolving it into a strategic partner embedded across the business.

• Hire and develop a team of Product Operations Managers to support stakeholders across Product, Engineering, Design, GTM, Customer Success, Operations, and more.

• Define PermitFlow’s Product operating system, including planning processes, PRD standards, launch processes, product metrics, customer feedback systems, and cross-functional collaboration models.

• Do hands-on Product Operations work yourself, particularly on the systems and programs that set the quality bar for the rest of the team.

• Own and evolve the systems that support Product planning, execution, launches, and measurement to ensure consistency, scalability, and clarity as the company grows.

• Establish consistent quality standards and review processes across the Product organization, ensuring teams have clear goals, requirements, success metrics, and launch plans.

• Partner closely with leadership to improve Product execution in ways that directly impact business metrics, including activation, retention, customer satisfaction, and product velocity.

• Set the vision for how AI transforms the Product Operations function, driving adoption of AI tools and evolving workflows across the team.

What We’re Looking For

We’re open to calibrating the level of this role based on the candidate’s experience and scope of impact, from Manager through Head of Product Operations. We’re ultimately looking for the strongest product operations leader for the business, with title and scope matched to their track record and leadership experience.

• 8+ years of experience in Product Operations, Business Operations, Strategy & Operations, or B2B SaaS product leadership. Experience supporting complex workflow products with data-heavy systems and cross-functional stakeholders.

• 3+ years of experience leading and managing teams, ideally in a high-growth startup or technology company.

• Proven experience building Product Operations teams and functions from early-stage to scale.

• Exceptional operational judgment across planning, prioritization, product development, launches, measurement, and cross-functional execution. Systems thinking, not just strong project management.

• Player-coach mentality with the ability to do hands-on Product Operations work while simultaneously building and scaling a team.

• Active AI fluency, with AI tools integrated into your daily operating workflow. Strong opinions on how AI is changing the way Product Operations teams work and a track record of evolving your own process accordingly.

• Strong experience standing up Product operating processes, including planning rituals, PRD quality standards, launch readiness, product reviews, customer feedback systems, and product metrics.

• Excellent communication and collaboration skills, with the ability to partner closely with Product and Engineering leadership and hold your own in strategic and technical conversations.

• Ability to balance strategic thinking with hands-on execution in a fast-moving environment.

What We Offer

• Competitive salary and meaningful equity in a high-growth company

• 100% company-paid base medical, dental, and vision coverage for employees + healthcare FSA

• 401(k) savings plan

• Unlimited PTO and paid family leave

• Home office & equipment stipend

• Daily in-office lunch and dinner provided

• Commuter benefits (pre-tax transit and parking)

Closing

If you’re excited by the opportunity to build AI-powered products that simplify complex real-world workflows - and want to help define a category from the ground up - we’d love to talk.

Inside PermitFlow: The Team Transforming Construction Permitting

PermitFlow provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, gender expression, or family status, as protected by applicable law.

We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. All employment decisions are based on merit, qualifications, and business needs.