Senior Manager/Director, Customer Success (Enterprise)

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.

What You Bring

• 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)