# Senior Manager/Director, Customer Success

**Company:** [Permitflow](https://hotfix.jobs/companies/permitflow)
**Location:** New York, NY
**Role:** Customer Success
**Salary:** $150k – $250k/yr
**Experience:** 8+ years
**Skills:** Customer Success, bi dashboards, customer health metrics, data-driven decision making, executive relationship management, retention strategies, expansion strategies, renewal management, Cross-Functional Collaboration
**Posted:** 2026-07-30

> Lead and scale the enterprise Customer Success team at PermitFlow, owning retention, expansion, and executive relationships for complex multi-region accounts in the construction AI space. Requires 8+ years in Customer Success with 4+ years managing teams carrying revenue targets.

## Job Description

## 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.

## 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 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.

## Benefits
- 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).

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