Lead Director - Strategic Customer Engagement Operations (Health100)

CVS Health; Boston (MA); On-site; USD 100,000 - 232,000; Full time

Benefits offered by this job

Medical insurance

Dental coverage

Vision coverage

Paid time off

Retirement savings

Wellness programs

Equity awards

Job summary

CVS Health is seeking a Lead Director, Strategic Customer Engagement Operations in the United States. You will manage Health100 client engagements from planning through follow-up, serving as a client-facing resource in discovery and pre-sales activities, and aligning internal resources to move opportunities forward.

The role requires coordinating senior executives, maintaining engagement momentum, and delivering cohesive reporting across the client portfolio in a fast-paced environment.

Qualifications

• 10+ years of experience in client engagement operations, business operations, chief of staff, or program operations.
• Experience coordinating engagements with senior executives, internal and external.
• Client-facing role with strong presence and communication against prospective/active clients.
• Exceptional organizational skills managing many engagements and stakeholders.
• Ability to convene cross-functional teams without direct authority.
• Ability to adapt in evolving environments.

Responsibilities

• Set engagement strategy and priorities across client portfolio.
• Lead client engagement planning with internal stakeholders and define objectives.
• Support discovery and pre-sales conversations to maintain momentum.
• Prepare leadership briefings with client context and capture outcomes.
• Maintain a consolidated view of engagement activity and report status.
• Adapt engagement plans as client needs evolve.

Skills

Client engagement leadership

Cross-functional coordination

Executive communication

Organizational skills

Healthcare/tech domain knowledge

Education

Bachelor’s degree or equivalent experience

Job description

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.

Education

• Bachelor’s degree, or equivalent experience (High School diploma + 4 years of relevant experience).

Pay Range

$100,000.00 - $231,540.00

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.

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: 11/15/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.