Executive Director, Customer Success Operations

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time. About Health100 Health100 serves as the trusted front door to health and care, putting the consumer at the center of everything we build. Among our offerings is industry-leading technology for pharmacies: a Pharmacy Management System that enables pharmacists to operate at the top of their license, and a consumer care and engagement platform that transforms how pharmacies connect with and serve the people who depend on them. Our technology is proven at scale, and we're bringing it to forward-thinking pharmacy operators who are ready to deliver a fundamentally better experience for their patients and communities. Customer Success (CS) Operations is foundational to the success of every customer we serve, ensuring each one receives a consistent, high-quality experience from day one and throughout the partnership. The Role The Director of CS Operations is the operational engine behind Health100's Customer Success organization. While our Customer Program Owners focus outward, building customer relationships and driving outcomes, you focus inward, building the operational framework that lets the whole team operate consistently and scale. You will design the processes, metrics, and tooling to support Health100 operations. You will also own some of our most operationally complex functions, including release coordination across multiple product lines that sit at the intersection of CS and our Engineering and Product teams. The foundation you build now will determine whether CS can scale smoothly from a handful of customers to a much larger portfolio without losing quality. What You Will Do Build and Run the CS Operating Rhythm Design and run the cadences that keep CS leadership informed and aligned: team reviews, portfolio health reporting, executive governance, and commitment tracking. Maintain a clear, current view of every customer across all phases: where implementations stand, what is at risk, what commitments are open, and what is coming up on each customer's calendar. Be the organizational memory for the CS team, ensuring that decisions, commitments, and context are documented. Give the CS leadership team the visibility they need to make good resourcing, escalation, and prioritization decisions. Coordinate Customer Release Activation Serve as the primary operational bridge between the CS team and Health100's product release processes, which run independently across multiple product lines. Translate customer-facing decisions about when to activate a new capability, what testing is needed, and how to sequence across products into the scheduling and execution artifacts that Engineering and Deployment teams need to act on. Build and maintain working relationships with each product's release leads so that customer activation needs are anticipated, not surprised. Aggregate across the per-product relationships to give CS leadership a single coherent multi-product view of release activity and risk. Surface conflicts between customer timelines and product release calendars early, and work with CS leadership to resolve them before they become customer issues. Standardize, Measure, and Improve Build the playbooks that make CS repeatable: for implementation kickoffs, release activations, business review preparation, escalation handling, go-live, and steady-state operations. Own the CS tech stack: Customer relationship management documentation, project tracking, and reporting. Make these tools work for the team, not the other way around. Identify where CPOs are solving the same problems independently and turn those patterns into shared, standardized approaches. Who You Will Work With Customer Program Owners: the customer-facing team you enable. You are their operational backbone, standardizing what should be consistent and clearing the path for what is unique. Technical Account Management: The inward and outward technical engines that support the client. Product Release leads: your counterparts for coordinating customer activation across Health100's product lines. You will build standing working relationships with each of them. Product Deployment teams: execution partners for implementation across the customer base. Customer Insights: close collaboration on defining and instrumenting the metrics that reflect CS and customer health. CS Leadership and SVP: you produce the portfolio visibility and governance reporting that enables good decisions at the top of the organization. What We Are Looking For Required 15+ years of experience in CS Operations or a similar operational function in enterprise software. Demonstrated experience building or scaling operational infrastructure including playbooks, metrics frameworks, and tooling in a CS or post-sales organization. Fluency in enterprise software release and deployment mechanics: release trains, change management, configuration management, release cadences. Structured, systematic thinker who documents decisions, builds repeatable processes, and treats the absence of a playbook as a gap to close, not a feature. Strong cross-functional coordination ability. This role holds relationships with Engineering, Product, Release Management, and Deployment. Data fluency: able to define what to measure, interpret operational metrics, and translate data into actionable CS leadership visibility. Preferred Experience in healthcare IT, pharmacy technology or enterprise technology Prior experience standing up a Customer Success Ops function or significantly expanding one during a period of rapid customer growth. Familiarity with multi-product organizational models with separate release practices and matrix reporting relationships. Experience with configuration management principles and tooling in complex enterprise deployments. Pay Range The typical pay range for this role is: $131,500.00 - $303,195.00 This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program. Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong. Great benefits for great people We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families. This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility. Additional details about available benefits are provided during the application process and on Benefits Moments. We anticipate the application window for this opening will close on: 07/27/2026 Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws. Our Work Experience is the combination of everything that's unique about us: our culture, our core values, our company meetings, our commitment to sustainability, our recognition programs, but most importantly, it's our people. Our employees are self-disciplined, hard working, curious, trustworthy, humble, and truthful. They make choices according to what is best for the team, they live for opportunities to collaborate and make a difference, and they make us the #1 Top Workplace in the area.