Chief of Staff

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.

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.

About the Role

The Chief of Staff is the CEO's primary thought partner and operational extension. You'll work directly with Francis (our CEO) on an increasingly complex and critical basket of priorities, with full access to our decision-making and internal reflections. This role spans executive alignment, strategic project leadership, and confidential communications, with broad exposure to our leadership team, partners, customers, and investors.

You are a problem solver and self-organizer who thrives in ambiguity. You love being given ambitious goals and the freedom to figure out how to get there. From day one, you'll have responsibility and access beyond your tenure. We're looking for high-drive, high-horsepower operators who are excited to help take PermitFlow to the next level.

What You'll Do

• Serve as the CEO's Thought Partner: Act as a sounding board across all topics related to the company and support the CEO in executing priority tactical and strategic work.

• Drive Strategic Projects End-to-End: Spearhead specific strategic projects in high-priority business areas: scoping, setting goals and success metrics, and reporting on outcomes.

• Hold Executive Accountability: Drive senior executives to ensure execution on the most immediate and critical priorities and keep a consistent accountability loop on leadership action items.

• Act as a Force Multiplier: Collaborate across functions to align teams and accelerate progress. This is a cross-functional role; your success is tied closely to the success of the functions you support.

• Handle Executive-Level Matters: Manage confidential communications, strategic decisions, and executive-level matters with professionalism and empathy.

Who You Are

• Dual-track background: 4+ years of aggregate experience across top-tier management consulting or financial services (private equity, investment banking, or venture capital) and strategy and operations at a high-growth startup. Both legs are required.

• Strategic operator: proven experience in operational strategy development, with a track record of improving efficiency and driving growth.

• Execution-oriented: proven experience implementing and executing key initiatives in fast-paced, ambiguous environments.

• Adaptable: strong problem-solving skills and operational agility; you make good decisions quickly when the path is not fully defined.

• Analytical: we are a data-driven company. You are very comfortable in Excel and other data tools.

• Clear communicator: we communicate heavily via writing. You are a concise writer who can bring your audience along through your thought process and analysis.

• Strong work ethic: from day one, you will have responsibility and access beyond your tenure. You are excited to take on those challenges alongside the CEO.

• Team player: you see the success of the functions you support as your own success.

• Hybrid in NYC: in office Monday, Wednesday, and Friday in our Manhattan office.

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)

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.