Head of Customer Success

PermitFlow is revolutionizing construction permitting with an AI workforce, accelerating housing development and clean-energy projects. They are seeking a seasoned Head of Customer Success to lead their CS team, build scalable programs, and drive customer satisfaction, retention, and growth. This role involves managing the post-sale customer lifecycle, overseeing CSMs, and owning renewal and expansion motions, including deal structuring and upsell strategies.

Must Have

• 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 systematic post-sales processes tracked through CRM and ensure seamless customer experience.
• Be accountable for and report on retention and expansion performance metrics (e.g., NRR, churn).
• Build strong executive relationships to drive satisfaction, loyalty, and advocacy.
• Maintain a constant pulse on customer health and proactively identify churn risks.
• 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.
• Translate customer insights into actionable feedback to inform Product development.
• Collaborate closely with Sales to align on account strategy and identify revenue opportunities.
• Partner with Operations to streamline client communications throughout the permitting process.
• 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 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.

Good to Have

• Experience in construction tech

Perks & Benefits

• Competitive Salary
• Equity packages
• 100% Paid health, dental & vision coverage
• Lunch & Dinner provided w/ a fully stocked kitchen
• Commuter benefits
• Unlimited PTO

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