Director, Customer Success (Enterprise)

The role

You will lead, grow, and scale the enterprise Customer Success team. You will own the enterprise book of business and execute success strategies to drive retention, expansion, and advocacy for large customers.

What you will do

• Lead, mentor, and develop a team of 8 Enterprise Customer Success Managers.
• Own gross and net retention for the enterprise segment.
• Build and own the enterprise engagement model.
• Partner with CSMs to identify at-risk customers and deploy proactive success plans.
• Serve as an executive sponsor and escalation point for C-suite and VP-level relationships.
• Ensure the team delivers measurable outcomes aligned with customer and business goals.
• Partner cross-functionally with Sales, Product, and Operations.
• Act as a champion of customer insights to inform strategic decisions.

Required qualifications

• 4+ years of experience in a people leadership position in Customer Success, including 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

Benefits

• Competitive salary
• Meaningful equity
• 100% company-paid base medical, dental, and vision coverage for employees
• healthcare FSA
• 401(k) savings plan
• Unlimited PTO
• paid family leave
• Home office & equipment stipend
• Daily in-office lunch and dinner provided
• Commuter benefits (pre-tax transit and parking)

About the company

PermitFlow is an applied AI company serving the nation's builders. It helps construction companies navigate permitting, licensing, inspections, and project closeouts.