Enterprise Customer Success Director — Retention & Growth

PermitFlow; New York (NY); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Equity

Medical coverage

401(k) savings plan

Unlimited PTO

Home office stipend

Daily in-office lunch and dinner

Commuter benefits

Job summary

PermitFlow, an applied AI company redefining how America builds, is seeking an experienced Director, Customer Success to lead our enterprise CS team in New York City. In this hybrid role, you’ll own the enterprise book of business across multi-branch and multi-region accounts, shaping retention and expansion with executive stakeholders.

You’ll mentor 8 Enterprise CSMs, drive patient-long-term adoption, and partner with Sales, Product, and Operations to align roadmaps with customer outcomes.

Qualifications

• 4+ years in people leadership in Customer Success with retention or revenue ownership.
• 8+ years in Customer Success with enterprise, multi-stakeholder accounts.
• Experience owning executive relationships with senior buyers at large organizations.

Responsibilities

• Lead and develop a team of 8 Enterprise Customer Success Managers.
• Own gross and net retention for the enterprise segment.
• Build the enterprise engagement model: executive reviews, mutual success plans, multi-threaded relationship maps, and rollout plans across branches, regions, or business units.
• Partner with CSMs to identify at-risk customers and deploy proactive success plans.
• Serve as an executive sponsor and escalation point with C-suite and VP-level relationships at key accounts.
• Ensure the team delivers measurable outcomes aligned with customer objectives and PermitFlow's goals.
• Partner cross-functionally with 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.

Skills

People leadership

Enterprise CS leadership

Executive relationships

BI dashboards & metrics

Data-driven decision making

Startup / high-growth experience

Tools

CRM systems

BI dashboards

Job description

PermitFlow, an applied AI company redefining how America builds, is seeking an experienced Director, Customer Success to lead our enterprise CS team in New York City. In this hybrid role, you’ll own the enterprise book of business across multi-branch and multi-region accounts, shaping retention and expansion with executive stakeholders.

You’ll mentor 8 Enterprise CSMs, drive patient-long-term adoption, and partner with Sales, Product, and Operations to align roadmaps with customer outcomes.