As the Senior Director of Customer Success you will lead our Principal Customer Success Managers (5-7) and two frontline Senior CSM Managers, across Jumbo, Enterprise and Mid-Market segments. Reporting to the SVP, Customer Success, this role is part of our broader Customer Success organization and is key to helping customers realize value, deepen engagement, and achieve measurable outcomes.

Please note that this is a hybrid role based in New York City, with an expectation to be in office 3 days a week. Our office is located at 60 Madison Avenue.

What you’ll do:

• Retention & growth: Own gross / net revenue retention targets and utilization targets to drive post-sales (consumption-based) revenue. Partner with Revenue Operations and Account Management to forecast renewals and surface upsell opportunities.
• Customer outcomes at scale: Design and evolve data-driven playbooks and health-score models that increase activation, utilization, and wellbeing impact while ensuring retention across the book of business.
• Segment strategy: Tailor engagement models by customer size, industry, and program maturity.
• Executive advocacy: Act as senior sponsor for key accounts; guide QBRs and ABRs, executive business reviews, and escalations.

How you’ll lead

• Develop people & culture – coach two CSM Managers and their teams; hire, onboard, and promote with an eye toward inclusivity and career pathing. Mentor Principal CSMs and support the team throughout the customer lifecycle.
• Build systems & insights – iterate on Gainsight, Salesforce, and Looker dashboards that turn customer data into action.
• Orchestrate the customer journey – ensure seamless hand-offs across Implementation, Clinical Ops, Product, and Support.

What success looks like in this role:

• Net Revenue Retention (110%)
• Renewal Retention (92%)
• Supporting upsell target ($25M)
• and supporting VR

What you’ll bring:

• 10+ years in Customer Success / Account Management within B2B SaaS; 5+ years leading multi-layer teams that serve Fortune 500 enterprises.
• Proven record hitting >95 % gross retention and driving expansion in a consultative, data-guided selling motion.
• Executive presence, superb storytelling, and ability to influence C-suite stakeholders internally and externally.
• Comfort operating in a high-growth, mission-driven environment; healthcare or HR-tech experience is a plus.

What we’d love to see:

• Familiarity with benefits administration, mental-health solutions, or outcomes-based pricing models.
• Fluency in data visualization to convey impact and ROI to HR and Finance leaders.
• Familiarity with Gainsight, SalesForce, Asana, JIRA and Google Suite

The target base salary range for this position is $184,000 - $230,000, and is part of a competitive total rewards package including stock options and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay.

Benefits provided by Spring Health:

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals.
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub, which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.