Lead Director, Strategic Planning

CVS Health•Work At Home-Texas, TX

4d•$100,000 - $231,540•Remote

About The Position

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 Chief of Staff (CoS) to the SVP of Employer Sales is a strategic and execution partner responsible for strengthening renewal strategy, improving delivery reliability, and increasing overall leadership effectiveness across the Sales and Account Management organization. This role improves decision quality, installs a disciplined operating rhythm, and ensures early alignment between renewal strategy, pricing intent, and delivery readiness. The CoS acts as an objective filter for issues and initiatives brought to the SVP—clarifying priorities, surfacing trade-offs, and ensuring follow-through on the work that matters most. The role is both highly strategic and strongly execution-oriented, with a focus on reducing late-stage renewal risk, preventing delivery failures, and enabling the SVP and leadership team to operate with clarity and confidence.

Requirements

10+ years of experience within the PBM or health plan space with 5+ years of experience specifically in strategy, operations, consulting, sales enablement, or chief-of-staff–type roles.
Proven experience leading complex, cross-functional initiatives with executive visibility.
Strong execution, prioritization, and follow-through skills.
High level of comfort with data, performance measurement, and trend analysis.
Excellent judgment, problem-solving, and executive communication skills.
Ability to influence without direct authority.

Nice To Haves

Experience in healthcare, employer-facing sales, or account management organizations.
Pharmacy benefit management or health plan experience, particularly with renewals, pricing strategy, and delivery coordination.

Responsibilities

Renewal Strategy & Portfolio Risk Management: Own enterprise-level renewal and RFP readiness across Sales and Account Management. Maintain a forward-looking portfolio view of renewal health, including retention risk, margin pressure, consultant dynamics, and delivery reliability signals. Identify systemic risks and trends across accounts and escalate early with clear options and recommendations. Ensure renewal strategies are intentional, consistent, and aligned with enterprise goals.
Pricing and Delivery Alignment: Partner with Pricing, Finance, Operations, Product, and Account Management to ensure renewal commitments are operationally achievable. Pressure-test pricing and renewal strategies against delivery capacity and known constraints. Surface trade-offs when pricing, growth, or concession strategies introduce delivery or service risk.
Operating Rhythm and Execution Discipline: Own the operating cadence for the SVP and Sales Leadership Team, including agendas, pre-reads, action tracking, and decision logs. Establish dashboards and performance reviews that track renewal health, execution progress, and delivery risk. Ensure meetings drive decisions, ownership, and follow-through—not status updates.
Decision Quality and Executive Readiness: Develop concise, executive-ready decision briefs that frame options, risks, and recommendations. Track key decisions and ensure they are clearly communicated and executed across the organization. Improve consistency and discipline in how high-stakes decisions are made and implemented.
Leadership Team Effectiveness: Support stronger coordination between Sales and Account Management leaders within the SVP’s organization. Improve role clarity, escalation paths, and alignment around renewal ownership and execution. Surface patterns related to leadership capacity, coverage gaps, and skill needs that could impact renewals or delivery.