Sr. Manager/Director, Customer Success

What You'll Do

• 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.

Requirements

• 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 time spent in a midmarket segment.
• 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).