Customer Success Director

Castlight Health; United States; On-site; USD 131,000 - 197,000; Full time

Job summary

Castlight Health is seeking a seasoned Customer Success Director to define and drive the organization's customer success strategy for its largest clients in healthcare. You will shape engagement models, metrics, and lifecycle frameworks, and own executive relationships across a diverse set of health‑tech partners.

You will lead the design and refinement of retention strategies, health scoring, and data‑driven growth initiatives, collaborating with sales, clinical, and product leaders to align

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.
• Strong analytical capability with experience building portfolio-level performance frameworks.
• Expert knowledge of health plan, employer, or value-based care markets.
• MBA or advanced degree preferred.

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, executive level engagement on program direction, escalation, and growth.
• Lead design and 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 priorities.
• Evaluate and drive adoption of technology and tooling that scales customer success capabilities.
• 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 relationships

Data‑driven retention

Leadership

Portfolio performance

Education

Bachelor's degree

MBA or advanced degree preferred

Job description

• CANDIDATES WITH STRONG LABOR AND UNION EXPERIENCE HIGHLY PREFERRED

Job Description Summary

• CANDIDATES WITH STRONG LABOR AND UNION EXPERIENCE HIGHLY PREFERRED

Defines the organization’s customer success strategy and sets the standard for how the organization engages, retains, and grows its most important client relationships. Acts as the enterprise expert on customer success model design, client lifecycle management, and portfolio performance optimization.

Shapes both the programmatic and relationship dimensions of customer success at the highest level, influencing commercial outcomes and long-term client loyalty.

The Customer Success Director drives short- to mid-term strategy for the discipline and exercises independent judgment on novel, cross-functional problems. This job operates as a subject-matter expert across multiple functional areas, designing engagement and retention strategies where no established precedent exists within the function, and influences both functional and cross-functional strategy.

How Will You Make An Impact & Requirements

Key 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 matters of program direction, escalation, 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.

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.
• Strong analytical capability with experience building portfolio-level performance frameworks.
• Expert knowledge of health plan, employer, or value-based care markets.
• MBA or advanced degree preferred.

Compensation Range

$131,243.00 to $196,865.00

The anticipated base salary range represents the Company's good-faith estimate of the compensation it reasonably expects to pay for this position at the time of posting. Actual compensation will be determined based on factors including experience, skills, qualifications, geographic location, internal equity, and business needs.