Sr. Manager/Director, Customer Success (Midmarket)

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.

You Have:

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