Enterprise CS Director — Retention & Executive Growth

PermitFlow; United States; Hybrid; USD 150,000 - 230,000; Full time

Benefits offered by this job

Equity

Medical/dental/vision coverage

401(k) savings plan

Unlimited PTO

Home office stipend

Lunch and dinner provided

Commuter benefits

Job summary

PermitFlow is seeking an experienced Senior Manager/Director, Customer Success to lead, grow, and scale our enterprise Customer Success team. You'll own the enterprise book of business, covering multi-branch and multi-region accounts with executive stakeholders and complex rollouts.

Reporting directly to the VP, Customer Success, you'll own team performance, operational excellence, and the execution of success strategies that drive retention, expansion, and advocacy with our largest and most

Qualifications

• 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

Responsibilities

• 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.

Skills

People leadership

Enterprise Customer Success

Executive relationships

Data-driven decision making

BI dashboards

Communication & coaching

Tools

CRM systems

Job description

PermitFlow is seeking an experienced Senior Manager/Director, Customer Success to lead, grow, and scale our enterprise Customer Success team. You'll own the enterprise book of business, covering multi-branch and multi-region accounts with executive stakeholders and complex rollouts.

Reporting directly to the VP, Customer Success, you'll own team performance, operational excellence, and the execution of success strategies that drive retention, expansion, and advocacy with our largest and most