Sr. Manager/Director, Customer Success (Midmarket)

- 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.

- 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

- Competitive salary and meaningful equity in a high-growth company

- 100% company-paid base medical, dental, and vision coverage for employees + healthcare FSA