Sr. Director of Client Success

ABOUT THE ROLE
The Sr. Director of Client Success will lead Rightway’s growing Client Success (CS) organization, driving the overall retention, satisfaction, and growth of our client portfolio across our two product lines–care navigation and pharmacy benefit management (PBM). This leadership role is responsible for ensuring that our clients receive maximum value from their relationship with Rightway while maintaining close collaboration with key departments such as Sales, Implementation, Service Delivery, Product, and Marketing.

As the senior leader of the CS function, the Sr. Director will shape the strategic vision, define goals, optimize operational processes, and create scalable systems to support business growth. This role also involves overseeing critical client relationships, managing escalation processes, and ensuring that the organization consistently exceeds client expectations through effective issue resolution and proactive support.

The ideal candidate is a strategic, relationship-driven leader with a deep operational acumen, a focus on driving measurable outcomes, and a hands-on approach when necessary to ensure both client and team success. This individual will thrive in a dynamic, fast-paced environment and be instrumental in scaling the CS function as the organization grows.

WHAT YOU’LL DO

• Recruit, develop, and scale a high-performing team of Client Success professionals, fostering a culture of continuous learning and growth. 
• Design and evolve the client segmentation and service model to optimize client coverage, account management, and team efficiency.
• Lead the CS function with a commercial mindset, ensuring that client success strategies are aligned with business objectives and drive profitable growth. Drive the development and execution of client renewal and growth (upsell/cross-sell) strategies, ensuring long-term success and value for clients. Support the sales team as needed on high value RFPs and finalist discussions.
• Build and maintain strong, multi-faceted relationships with key decision-makers at client organizations, navigating complex, high-stakes situations to ensure ongoing satisfaction and success. Serve as a trusted advisor in driving long-term client value and loyalty, handling sensitive and escalated issues with care and expertise.
• Implement a robust system for gathering and analyzing client feedback to identify areas for improvement and develop targeted strategies to address gaps.
• Develop and implement comprehensive playbooks, processes, and guidelines that ensure consistent, high-quality service delivery and enable the team to scale effectively. These resources should provide a framework for proactive client engagement, renewals, and growth.
• Partner with senior leaders across the organization to introduce new processes and initiatives that improve service quality and overall client experience.
• Lead strategic account planning with cross-functional involvement, ensuring actionable, timely, and effective execution of client plans.
• Hold the team accountable for delivering on key initiatives, including churn mitigation, member activation, and alignment with client deadlines and goals.
• Collaborate closely with departments such as Marketing, Service Delivery, Operations, Product, and Analytics to align on strategic initiatives, address client requests, and influence product roadmaps, particularly for customizations.
• Optimize the client handoff process from Implementation to Client Success to ensure seamless transitions and consistent service quality.
• Travel as needed to attend important client meetings, including kickoffs and strategic reviews, as well as broker and TPA meetings to foster client relationships.

ABOUT YOU

• 10-15+ years of relevant experience in client management, strategy consulting, complex sales, or operations 
• Minimum 3+ years of experience in the healthcare, health tech, or benefits industry
• Bachelor’s Degree required
• Experience leading and developing teams working with complex products 
• Operational excellence and ability to work cross-functionally
• Has had primary ownership in strategic account relationships for a sustained time period
• Excellent critical thinking skills, combined with the ability to present beliefs clearly and compellingly in verbal and written form, particularly the ability to convey technical / nuanced information in an accessible and understandable manner
• Ability to juggle several high-priority initiatives at once and continuously reprioritize to ensure the most impactful work is accomplished 
• Relationship oriented, with a high degree of comfort managing external stakeholders
• Adept at presenting in large groups, b