Head of Customer Success at PermitFlow (W22) $250K - $275K TurboTax for Construction Permitting New York City, NY Full-time US citizen/visa only 6+ years About PermitFlow PermitFlow is redefining how America builds. Pre-construction remains one of the most broken and manual parts of the $1.6T construction industry, causing massive delays, wasted capital, and lost opportunity across the built world. Our AI workforce delivers unprecedented speed, accuracy, and visibility to pre-construction — accelerating housing development, enabling clean-energy projects, and driving economic growth in communities nationwide. To date, we’ve powered over $20B in real estate development, helping builders and contractors move faster, reduce risk, and scale with confidence. We’re entering hypergrowth with clear product-market fit and a world-class team from top AI and construction companies. We’ve raised over $36.5M from Kleiner Perkins, Initialized Capital, Y Combinator, Felicis Ventures, and Altos Ventures, alongside backers from OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. We are on a mission is to modernize how the built world operates. About the role About Us PermitFlow is redefining how America builds. Pre-construction remains one of the most broken and manual parts of the $1.6T construction industry, causing massive delays, wasted capital, and lost opportunity across the built world. Our AI workforce delivers unprecedented speed, accuracy, and visibility to pre-construction — accelerating housing development, enabling clean-energy projects, and driving economic growth in communities nationwide. To date, we’ve powered over $20B in real estate development, helping builders and contractors move faster, reduce risk, and scale with confidence. We’re entering hypergrowth with clear product-market fit and a world-class team from top AI and construction companies. We’ve raised over $36.5M from Kleiner Perkins, Initialized Capital, Y Combinator, Felicis Ventures, and Altos Ventures, alongside backers from OpenAI, Google, Procore, ServiceTitan, Zillow, PlanGrid, and Uber. We are on a mission is to modernize how the built world operates. 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 We are seeking a seasoned and strategic Head of Customer Success to lead our CS team and drive exceptional customer outcomes. This individual will be responsible for building a scalable customer success program that ensures customer satisfaction, retention, and growth. This includes managing the entire post-sale customer lifecycle, overseeing a team of CSMs, and directly owning our renewal and expansion motion—including deal structuring, upsell strategies, and operational rigor. Key Responsibilities Customer Success Strategy & Leadership Define and execute scalable CS strategies across onboarding, adoption, retention, and growth. Lead and develop a high-performing team of CSMs with clear goals and KPIs. Build a systematic post-sales processes tracked through our CRM and collaborate cross-functionally to ensure a seamless customer experience. Be accountable to and report on retention and expansion performance metrics (e.g., NRR, churn). Customer Advocacy, Retention & Risk Management Build strong executive relationships to drive satisfaction, loyalty, and advocacy. Maintain a constant pulse on customer health and proactively identify churn risks. Surface actionable feedback to Product and other teams to enhance the customer experience. Renewals & Upselling Own the full renewal cycle, including forecasting, pricing, deal structuring, and negotiation. Establish and manage proactive renewal timelines and repeatable playbooks. Use Salesforce to systematically track renewals, expansion pipeline, and customer lifecycle milestones. Cross-Functional Collaboration Translate customer insights into actionable feedback to inform Product development and enhance the end-to-end user experience. Collaborate closely with Sales to align on account strategy, identify revenue opportunities, and drive upsell and renewal outcomes. Partner with the Operations team to streamline client communications related to project tracking, status updates, and overall engagement throughout the permitting process. Qualifications 8+ years of experience in Customer Success or Account Management, including 4+ years in a leadership role Previously scaled and managed CS teams at early-stage or growth-stage startups Proven track record of managing renewals and upsells, including deal structuring, renewal operations, and contract negotiations. Experience in B2B SaaS, preferably with technical products and/or startup environments. Strong communication, leadership, and project management skills. Experience implementing and managing CRM for CS pipeline and renewal management. Passion for building systems, teams, and processes from the ground up. Experience in construction tech is a huge plus! Even if you don’t meet 100% of the qualifications, we recommend applying to the role! Benefits: 💰 Competitive Salary 📈 Equity packages 🩺 100% Paid health, dental & vision coverage 🍽️ Lunch & Dinner provided w/ a fully stocked kitchen 🚍 Commuter benefits 🌴 Unlimited PTO