Lead Director - Strategic Customer Engagement Operations (Health100)

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. Position Summary The Lead Director, Strategic Customer Engagement Operations is responsible for the strategic management of Health100’s client engagements across prospective and active customers. This leader ensures Health100 is prepared for every client engagement, from planning and internal alignment through logistics and follow-up, and maintains a cohesive view of engagement activity across the client portfolio. This leader also serves as a client-facing point of contact in support of discovery and pre-sales engagements, helping move prospective clients from initial conversations toward agreement.   Key Responsibilities • Set engagement strategy and priorities across the client portfolio, sequencing engagements and meetings to advance each relationship toward its next milestone and aligning leadership time and internal resources accordingly. • Lead the planning and preparation of client engagements with the AVP of Customer Success, defining objectives and approach and confirming the right internal stakeholders and subject matter experts to engage at each stage, along with key messages beforehand. • Support discovery and pre-sales conversations with prospective clients, helping maintain momentum and advance opportunities toward agreement. • Prepare leadership for client interactions through briefings on client context, relationship history, and objectives, and capture outcomes, meeting notes, action items, owners, and next steps during and after the engagement to ensure clear and timely follow-up with clients and internal stakeholders. • Maintain a consolidated view of engagement activity across all clients, producing regular reporting for Customer Success leadership on status, upcoming milestones, and items requiring attention. • Adapt engagement plans and approach as client needs, priorities, and circumstances evolve, bringing structure and flexibility to a fast-paced environment. Required Qualifications • 10+ years of experience in client engagement operations, business operations, chief of staff, or program operations, including experience supporting complex enterprise pre-sales or prospective client engagements. Experience within healthcare and/or technology is strongly preferred. • Demonstrated experience coordinating engagements with senior executives, both internal and external. • Experience in a client-facing role, with the presence and communication skills to represent the organization directly with prospective and active clients. • Exceptional organizational skills, with the ability to manage many concurrent engagements, priorities, and stakeholders without losing detail. • Ability to convene and align cross-functional teams without direct authority, bringing in the appropriate stakeholders and subject matter experts based on client and engagement needs. • Ability to operate effectively in an evolving environment, demonstrating flexibility and the ability to pivot as client and business needs change. Preferred Qualifications • Experience within healthcare, healthcare technology, digital health, or enterprise technology. • Experience supporting complex enterprise pre-sales cycles, strategic pursuits, solution consulting, or technical discovery. • Experience working in a fast-paced, evolving environment where processes and operating models may still be developing. Ed