Senior Manager/Director of Customer Success (Midmarket)

About this role

• PermitFlow is seeking an experienced Sr Manager/Director, Customer Success to lead, grow, and scale our midmarket Customer Success team
• Reporting directly to the VP, Customer Success, you’ll own team performance, operational excellence, and the execution of success strategies that drive retention and advocacy across our midmarket book
• Lead, mentor, and develop a team of 7 midmarket Customer Success Managers, fostering a high-performance, customer-centric culture
• Own gross and net retention for the midmarket segment including adoption, expansion, and renewal
• Set and refine the midmarket coverage model, segmentation, and engagement cadence as the book scales
• Partner with CSMs to identify at-risk customers and deploy proactive success plans
• Lead customer escalations and executive communications, ensuring fast resolution and strong outcomes
• 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
• Act as a champion of customer insights to inform strategic decisions and prioritization

### Benefits

• Equity packages
• 100% Paid health, dental & vision coverage
• Company issued laptop
• Home office & equipment stipend
• Lunch & Dinner provides via UberEats w/ a fully stocked kitchen
• Commuter benefits
• Team building events
• Unlimited PTO- Strong analytical skills and comfort with BI dashboards, customer health metrics, and data-driven decision-making
• Experience in startup or high-growth environments, with a builder’s mindset and bias toward action
• 8+ years of experience in Customer Success, with time spent in a midmarket segment
• Adept at producing clear documentation, thoughtful analysis, concise internal communication, polished presentations, and direct, effective coaching
• 4+ years of experience in a people leadership position in Customer Success, including experience m...