Customer Success Director

Castlight Health, Inc; San Francisco (CA); On-site; USD 131,000 - 197,000; Full time

Job summary

Castlight Health, Inc. in San Francisco is seeking a Customer Success Director to define the organization’s CS strategy, engage senior clients, and drive portfolio performance.

You will shape both programmatic and relationship dimensions of CS at the highest level and influence enterprise outcomes. You will own top client relationships, design CS infrastructure like health scores and QBRs, and partner with Sales, Clinical, and Product leadership to align priorities.

Qualifications

• Bachelor's degree required; 12+ years of experience in customer success strategy or enterprise account leadership.
• Experience designing and scaling customer success programs with retention and growth outcomes.
• Exceptional executive relationship management and communication skills.
• Strong analytical capability with experience building portfolio-level performance frameworks.
• 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, personally engaging at the executive level on 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 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

Analytical capability

Portfolio performance

Education

Bachelor's degree

MBA or advanced degree

Job description

Job Description Summary**CANDIDATES WITH STRONG LABOR AND UNION EXPERIENCE HIGHLY PREFERREDDefines the organization’s customer success strategy and sets the standard for how the organizationengages, retains, and grows its most important client relationships. Acts as the enterprise expert oncustomer 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 exercisesindependent judgment on novel, cross-functional problems. This job operates as a subject-matter expertacross multiple functional areas, designing engagement and retention strategies where no establishedprecedent exists within the function, and influences both functional and cross-functional strategy.How will you make an impact & RequirementsKEY RESPONSIBILITIES• Set the strategic vision for customer success across the organization, defining engagementmodels, success metrics, and client lifecycle frameworks.• Own relationships with the most strategically significant clients, personally engaging at theexecutive level on matters of program direction, escalation, and growth.• Lead design and continuous refinement of customer success infrastructure, including healthscoring, QBR formats, and data-driven retention frameworks.• Partner with sales, clinical, and product leadership to align customer success strategy withenterprise commercial and product priorities.• Evaluate and drive adoption of technology and tooling that scales customer success capabilitiesacross 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 enterpriseaccount leadership in healthcare or health technology.• Deep expertise in designing and scaling customer success programs with direct accountability forretention 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:$131,243.00to$196,865.00The 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.