Strategic Enterprise Customer Success Director

Castlight Health; Northern (KY); Hybrid; USD 131,000 - 197,000; Full time

Job summary

Castlight Health seeks a seasoned Director of Customer Success to define strategic engagement, retention, and growth for our enterprise clients. You will own executive relationships, design scalable success programs, and collaborate with sales, product, and clinical teams to align client outcomes with business goals.

The role requires 12+ years in customer success or enterprise leadership in healthcare, with MBA preferred.

Qualifications

• Bachelor's degree required; 12+ years of experience in customer success strategy or enterprise account leadership in healthcare or health technology.
• Deep expertise in designing and scaling customer success programs with direct accountability for retention and growth outcomes.
• Exceptional executive relationship management and communication skills.

Responsibilities

• Set the strategic vision for customer success across the organization, defining engagement models, success metrics, and client lifecycle frameworks.
• Own relationships with the most strategically significant clients, personally engaging at the executive level on program direction and growth.
• Lead design and continuous refinement of customer success infrastructure, including health scoring, QBR formats, and data-driven retention frameworks.
• Partner with sales, clinical, and product leadership to align customer success strategy with enterprise commercial and product priorities.
• Evaluate and drive adoption of technology and tooling that scales customer success capabilities across the team.
• Lead customer success professionals, setting quality expectations, establishing team standards, and developing functional expertise.
• Synthesize portfolio-level performance insights to advise senior leadership on client satisfaction, retention risk, and expansion opportunity.

Skills

Executive relationship management

Portfolio performance insights

Data-driven retention strategies

Education

Bachelor's degree

MBA or advanced degree preferred

Job description

Castlight Health seeks a seasoned Director of Customer Success to define strategic engagement, retention, and growth for our enterprise clients. You will own executive relationships, design scalable success programs, and collaborate with sales, product, and clinical teams to align client outcomes with business goals.

The role requires 12+ years in customer success or enterprise leadership in healthcare, with MBA preferred.