Sr. Manager/Director, Customer Success (Midmarket)

• Lead, mentor, and develop a team of 7 midmarket Customer Success Managers, fostering a high-performance, customer-centric culture.
• Own gross and net retention for the midmarket segment including adoption, expansion, and renewal.
• Set and refine the midmarket coverage model, segmentation, and engagement cadence as the book scales.
• Partner with CSMs to identify at-risk customers and deploy proactive success plans.
• Lead customer escalations and executive communications, ensuring fast resolution and strong outcomes.
• 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.
• Act as a champion of customer insights to inform strategic decisions and prioritization.

• 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 time spent in a midmarket segment
• 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

• 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 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 Sr Manager/Director, Customer Success to lead, grow, and scale our midmarket Customer Success team. Reporting directly to the VP, Customer Success, you'll own team performance, operational excellence, and the execution of success strategies that drive retention and advocacy across our midmarket book.

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