RoleSword is hiring a Senior Customer Success Manager to own a portfolio of approximately 20 to 30 enterprise employer relationships. You will proactively surface renewal blockers, manage retention and renewals, and help benefits leaders and their advisors connect member access, engagement, outcomes, and financial value to clear decisions.
This role is for someone who can move from executive strategy to operating detail. You will diagnose what is blocking customer value, involve the right partners across Sword, and maintain a credible customer plan even when the process or internal owner is unclear.
What you'll be doing- Build proactive account and renewal plans, identify risk early, and focus high-touch engagement where it can materially change the outcome.
- Own retention strategy, pricing and contracting coordination, executive relationships, and risk plans across a portfolio of consequential enterprise accounts.
- Build multithreaded relationships with benefits leaders, consultants, finance, clinical, procurement, and operational stakeholders, adapting the value story to each decision-maker.
- Use eligibility, enrollment, activation, engagement, outcomes, claims, billing, and ROI evidence to diagnose account performance; understand how file specifications and data-flow issues affect customer confidence and results.
- Secure the customer access and communication permissions needed to reach eligible members and improve enrollment, activation, and sustained engagement.
- Identify cross-functional breakdowns, engage the right partners across Sales, Growth Marketing, Implementation, Product, Clinical, Analytics, Finance, and Operations, and keep the customer informed through resolution.
What you need to have- Significant experience personally owning complex enterprise customer or client relationships after implementation, including renewals, retention, and account recovery.
- Evidence of using quantitative customer-value data to make decisions and influence senior stakeholders.
- Strong executive communication and the judgment to navigate competing customer, consultant, and internal priorities.
- A record of identifying cross-functional breakdowns and engaging the right teams to execute a solution.
- Comfort operating in a remote, fast-moving environment where priorities change and a process or owner may not yet be defined, while managing multiple consequential accounts and traveling up to 15%.
What we'd love to see- Employer health benefits, digital health, benefits navigation, wellbeing, PBM, or closely related experience.
- Direct work with enrollment, utilization, claims, outcomes, ROI, billing, or member-engagement data.
- Experience managing complex portfolios through multiple renewal cycles and organizational change.
How success will be measuredIn your first year, you will establish proactive renewal and retention plans, surface blockers earlier, expand access to eligible members where access is limiting results, and build executive and consultant relationships that increase confidence in Sword's value.
*The range below reflects base, variable, and equity for this role.
This is a starting point, not a ceiling - once someone joins and proves they're outlier talent, we adjust quickly to make sure their compensation matches their impact.
Job titles may span more than one career level, so actual pay depends on skills, qualifications, experience, location, and market demand, among other factors. The range reflects base salary plus any variable, bonus, or sales incentives, and our estimate of the value of private company stock options where applicable. It's subject to change, and future stock value isn't guaranteed. Sword also offers additional benefits beyond total compensation.
Total Compensation Range
$136,850-$215,050 USD
Country-specific benefits may vary and will be detailed separately.
