Director Customer Success - Enterprise

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.

PermitFlow is seeking an experienced Director, Customer Success to lead, grow, and scale our enterprise Customer Success team. You'll own the enterprise book of business, covering multi-branch and multi-region accounts with executive stakeholders and complex rollouts. Reporting directly to the VP, Customer Success, you'll own team performance, operational excellence, and the execution of success strategies that drive retention, expansion, and advocacy with our largest and most complex customers.

This is a hybrid role based in our New York City office (in-office Monday, Wednesday, and Friday).

What You'll Do:

• Lead, mentor, and develop a team of 8 Enterprise Customer Success Managers, fostering a high-performance, customer-centric culture.

• Own gross and net retention for the enterprise segment, including multi-stakeholder adoption, expansion, and renewal.

• Build and own the enterprise engagement model: executive business reviews, mutual success plans, multi-threaded relationship maps, and structured rollout plans across branches, regions, or business units.

• Partner with CSMs to identify at-risk customers and deploy proactive success plans, with direct involvement in the highest-value accounts.

• Serve as an executive sponsor and escalation point, holding C-suite and VP-level relationships at key accounts.

• Ensure the team delivers measurable outcomes that align with both customer objectives and PermitFlow's business goals.

• Partner cross-functionally with leaders across Sales, Product, and Operations to improve the customer experience and shape roadmap priorities for enterprise needs.

• Act as a champion of customer insights to inform strategic decisions and prioritization.

You Have:

• 4+ years of experience in a people leadership position in Customer Success, including experience managing a team carrying a retention or revenue number

• 8+ years of experience in Customer Success, with meaningful time in an enterprise segment managing complex, multi-stakeholder accounts

• Experience owning executive relationships with senior buyers at large organizations

• Strong analytical skills and comfort with BI dashboards, customer health metrics, and data-driven decision-making

• Adept at producing clear documentation, thoughtful analysis, concise internal communication, polished presentations, and direct, effective coaching

• Experience in startup or high-growth environments, with a builder's mindset and bias toward action

What We Offer (Full-Time Roles Only)

• 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.