Director of Client Success

About Leap: Leap is a rapidly growing benefits solutions company and a pioneer in employer specialty pharmacy. They are transforming how life-changing therapies are delivered and financed, ensuring patients receive necessary treatments while employers achieve fair pricing and improved access. Specialty drugs and infusions account for nearly 10% of healthcare spending and are the fastest-growing cost category for employers. Leap addresses this by eliminating hidden markups, expanding access to high-quality infusion providers, and ensuring clarity and fairness in therapy pricing and payment.

Leap partners with numerous Fortune 500 companies and leading Third-Party Administrators (TPAs). Each patient served delivers immediate ROI for employers through lower costs, improved access, and better care.

About the Role:

The Director of Client Success leads Leap’s team of senior Strategic Client Success Managers and oversees the systems that deliver a premium client experience while the company grows at high velocity. This role involves managing and developing a team of experienced client leaders who handle strategic relationships with employers, TPAs, Pharmacy Benefit Managers (PBMs), and benefits consultants. Additionally, you will manage executive relationships with Leap’s most strategic clients and serve as the senior escalation point for the team.

This is a builder role. With the client base growing faster than the team, the next stage requires establishing operating rhythms, escalation paths, and scalable account coverage models that maintain personalized client service.

The position reports to the SVP of Client Operations & Success.

What You'll Do:

Lead and Develop a Senior Team:

• Manage, coach, and grow a team of senior and principal-level Strategic Client Success Managers, setting clear expectations for account outcomes, client experience, and judgment.
• Hire and onboard new team members as the company scales, and design how accounts are assigned and balanced across the team.
• Build a culture where team members provide direct feedback to each other and confidently push back on clients with care.
• Conduct regular 1:1s, account reviews, and performance conversations to raise the team’s performance bar.

Build the Operating System for Client Success:

• Design and implement the team’s operating rhythm, including daily or weekly standups that quickly surface risks, blockers, and wins without unnecessary busywork.
• Create a clear escalation process, defining what the team resolves internally, what escalates to you, and what goes to clinical, operations, product, or executive leadership, with defined response times.
• Develop playbooks, account plans, health scoring, and renewal workflows that enable team members to manage more clients without compromising quality.
• Track and report on team and portfolio metrics, including retention, utilization, client satisfaction, and time to resolution.

Deliver White Glove Service at Scale:

• Ensure every client feels known and well-served, even as volume and pace increase.
• Set and enforce service standards for responsiveness, communication, and follow-through, holding the team accountable.
• Identify and fix process breakdowns before clients notice them.

Own Executive Client Relationships:

• Serve as the executive sponsor and senior escalation point for strategic employer, TPA, PBM, and consultant relationships.
• Lead or support quarterly and annual business reviews, translating utilization, savings, and member experience data into clear recommendations.
• Collaborate with Growth and Growth Marketing on renewals, expansion, finalist presentations, and client references.

Cross-Functional Leadership:

• Partner with clinical, operations, product, and support leaders to ensure seamless service delivery.
• Integrate structured client feedback into product and process decisions.
• Proactively identify portfolio-level risks and lead mitigation plans to protect retention.

What You Bring:

• At least 8+ years in client success, account management, or benefits consulting, with 4+ years managing a team of senior or principal-level individual contributors.
• Deep experience with employer-sponsored healthcare, including direct work with HR and Benefits leaders, TPAs, PBMs, or benefits consultants.
• A relationship-first leader who builds trust quickly with HR and Benefits executives, possessing strong executive presence and the ability to push back on clients when necessary.
• A track record of building team operating systems from scratch, including standups, escalation paths, playbooks, coverage models, and metrics.
• Proven results in gross and net revenue retention and client satisfaction across a growing book of business.
• Sound judgment on when to resolve issues internally and when to escalate, with the ability to teach this judgment to a team.
• Experience in a startup or growth-stage environment, comfortable with rapid business development.
• Humble and growth-oriented, comfortable receiving direct feedback from multiple senior leaders in a flat, fast-moving organization.
• Ability to translate retention, utilization, and savings data into clear stories for senior client stakeholders.
• Willingness to travel up to 30%.