Director of Client Success

About Leap

Leap is one of the fastest-growing benefits solutions and a category-defining pioneer in employer specialty pharmacy. We are reshaping how life-changing therapies are delivered and financed, ensuring patients get the treatment they need while employers finally get a fair deal.

Specialty drugs and infusions represent nearly 10% of all healthcare spend and are the fastest-growing cost category for employers. Leap tackles this challenge with a novel approach: eliminating hidden markups, expanding access to high-quality infusion providers, and bringing clarity and fairness to how therapies are priced and paid for.

We’re proud to partner with numerous Fortune 500 companies and leading TPAs. Each patient we serve creates immediate ROI: lower costs, improved access, and better care. Join us as we redefine what’s possible in specialty care.

About the Role

The Director of Client Success leads Leap's team of senior Strategic Client Success Managers and owns the systems that let us deliver a white glove experience to every client while the business grows at extreme velocity. You will manage and develop a team of experienced, principal-level client leaders who each own strategic relationships with employers, TPAs, Pharmacy Benefit Managers (PBMs), in partnership with the benefits consultants.

You will also carry executive relationships with our most strategic clients and be the senior point of escalation for the team.

This is a builder role. Our client base is growing faster than our team, and the next stage requires operating rhythms, escalation paths, and account coverage models that scale without making any client feel like a number. This position reports to the SVP of Client Operations & Success.

WHAT YOU'LL ACCOMPLISH

• 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 we scale, and design how accounts are assigned and balanced across the team
• Build a culture where team members give direct feedback to each other and push back on clients with confidence and care
• Run regular 1:1s, account reviews, and performance conversations that raise the bar for the whole team
• Build The Operating System For Client Success
• Design and run the team's operating rhythm, including a daily or weekly standup that surfaces risks, blockers, and wins quickly without adding busywork

Create a clear escalation process: what the team resolves on its own, what comes to you, and what goes to clinical, operations, product, or executive leadership, with defined response times

Build playbooks, account plans, health scoring, and renewal workflows that let each team member manage more clients without losing quality

Track and report on team and portfolio metrics, including retention, utilization, client satisfaction, and time to resolution

Develop a team that knows how to launch and upsell clients to the best benefit plan design that drives the highest engagement.

• The leader will know how to overcome barriers and strong negotiating skills
• Deliver White Glove Service At Scale
• Make sure every client feels known and well served, even as volume and pace increase
• Set service standards for responsiveness, communication, and follow through, and hold the team to them
• Spot where process is breaking under growth and fix it before clients feel it
• Own Executive Client Relationships
• Serve as the executive sponsor and senior escalation point for our most strategic employer, TPA, PBM, and consultant relationships
• Lead or support quarterly and annual business reviews that translate utilization, savings, and member experience data into clear recommendations
• Partner 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
• Bring structured client feedback into product and process decisions
• Proactively identify portfolio-level risk and lead mitigation plans to protect retention

WHAT WE'RE LOOKING FOR

• 8+ years in client success, account management, or benefits consulting, with at least 4 years managing a team of senior or principal-level individual contributors
• Deep experience with employer-sponsored healthcare, working directly with HR and Benefits leaders, TPAs, PBMs, or benefits consultants
• Experience working in start up environments or the pace of a start up
• A relationship-first leader who builds trust quickly with HR and Benefits executives, with strong executive presence and the backbone to push back on clients when it is the right call
• A track record of building team operating systems from scratch: standups, escalation paths, playbooks, coverage models, and metrics
• Proven results on gross and net revenue retention and client satisfaction across a growing book of business
• Experience with carve out programs, navigation health plans, understanding HR leaders and their strategic planning
• Sound judgment on when to resolve an issue and when to escalate, and the ability to teach that judgment to a team
• Startup or growth-stage experience; comfortable building while the business moves quickly
• Humble and growth-oriented; comfortable taking direct feedback from multiple senior leaders in a flat, fast-moving organization
• Comfort turning retention, utilization, and savings data into a clear story for senior client stakeholders
• Willingness to travel up to 30%
• At Leap, we’re building an outlier company with real impact — and that takes focus, energy, and commitment. If that excites you, we’d love to hear from you.
• Leap is an equal opportunity employer and welcomes applicants from all backgrounds. We’re committed to building a team that reflects a diversity of perspectives, experiences, and identities.