Enterprise Customer Success Leader - Retention & Growth

PermitFlow; New York (NY); Hybrid; USD 170,000 - 230,000; Full time

Benefits offered by this job

Competitive salary

100% company-paid medical, dental, and

vision coverage

401(k) savings plan

Unlimited PTO

Home office & equipment stipend

Daily in-office lunch and dinner

Commuter benefits

Job summary

PermitFlow is seeking an experienced Senior Manager/Director of Customer Success to lead and scale our enterprise CS team in a hybrid New York City setting. You will own the enterprise book of business across multiple branches and regions, managing executive stakeholders and complex rollouts.

In this role you will mentor 8 Enterprise CSMs, drive retention and expansion, and partner with Sales, Product, and Operations to shape roadmaps.

Qualifications

• 4+ years in a people-leadership role in Customer Success, with retention/revenue ownership.
• 8+ years in Customer Success, with enterprise, multi-stakeholder accounts.
• Experience managing executive relationships with senior buyers.
• Strong analytics and data-driven decision making.
• Clear documentation, concise communication, and coaching.
• Startup or high-growth experience with a builder mindset.

Responsibilities

• Lead, mentor, and develop a team of Enterprise CSMs, fostering a high-performance culture.
• Own gross and net retention for the enterprise segment across multiple regions.
• Build and own the enterprise engagement model with executive reviews and rollout plans.
• Partner with CSMs to identify at-risk customers and deploy proactive plans.
• Serve as executive sponsor with C-suite relationships at key accounts.
• Ensure measurable outcomes align with customer objectives and PermitFlow goals.
• Collaborate across Sales, Product, and Operations to improve the customer experience.

Skills

People leadership

Enterprise CS

Executive relationships

Data-driven decisions

Documentation & communication

Startup experience

Tools

BI dashboards

Job description

PermitFlow is seeking an experienced Senior Manager/Director of Customer Success to lead and scale our enterprise CS team in a hybrid New York City setting. You will own the enterprise book of business across multiple branches and regions, managing executive stakeholders and complex rollouts.

In this role you will mentor 8 Enterprise CSMs, drive retention and expansion, and partner with Sales, Product, and Operations to shape roadmaps.