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CVS Health

Lead Director, Sales Enablement Strategic Initiatives

Posted Yesterday
Be an Early Applicant
In-Office or Remote
Hiring Remotely in Massachusetts, USA
100K-232K Annually
Expert/Leader
In-Office or Remote
Hiring Remotely in Massachusetts, USA
100K-232K Annually
Expert/Leader
Leads strategic sales enablement initiatives for Commercial and Specialty Markets, including value proposition development, sales pitches, field communications, client-facing content, and cross-functional execution. Oversees strategic sales experience activities and manages a team of business consultants, project managers, and communications professionals. Partners with senior leaders across Sales, Marketing, Product, Communications, and Strategy to improve sales effectiveness, retention, client engagement, and organizational transformation.
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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

**We are open to location for this remote or hybrid opportunity**

The Lead Director, Sales Enablement Strategic Initiatives is responsible for advancing Commercial & Specialty Markets' strategic priorities through value proposition and value story development, sales enablement consulting, field communications, and cross-functional execution. This leader serves as a trusted advisor to Commercial leadership and partners across Sales, Account Management, Product, Marketing, Communications, and Strategy to translate business objectives into scalable solutions, compelling value stories, sales pitches and actionable initiatives that drive growth and client engagement.

The role leads a team of business consultants, project managers and communications professionals dedicated to executing high-impact initiatives that support sales and retention efforts across Aetna's $30B Commercial & Specialty Markets business, serving more than 18 million medical members. 
What You Will Do

  • Lead high-priority strategic initiatives that support Commercial & Specialty Markets' growth, sales effectiveness, retention, and organizational transformation, partnering closely with senior leaders, the field and business stakeholders to drive execution and business results.

  • Provide strategic consulting and project leadership for complex strategic initiatives, cross-functional efforts, aligning stakeholders, managing competing priorities, and ensuring successful delivery of business objectives.

  • Drive Commercial's Go-to-Market Excellence strategy through the development of value propositions, sales pitches, enablement content, and field-facing resources that improve sales effectiveness and strengthen client engagement.

  • Own the development, governance, and continuous evolution of Commercial's Customer Conversation Content (CCC), the organization's core value proposition and sales enablement framework, ensuring a consistent and compelling narrative that brings Aetna's products, solutions, and capabilities to life for clients, prospects, and producer partners.

  • Oversee the Strategic Sales Experience team, including the development and delivery of customized sales and retention materials annually that support National Accounts, Public & Labor, and Large Group and DCS business priorities.

  • Oversee field communication strategies, ensuring sales and account management professionals remain informed about business-critical priorities, market trends, product updates, and enterprise initiatives.

  • Promote a culture of innovation and continuous improvement by challenging the status quo, embracing emerging technologies, and identifying new ways to deliver, activate, and measure the impact of sales enablement solutions.

  • Lead, develop, and mentor a team of business consultants and communications professionals by fostering a culture of accountability, collaboration, innovation, and continuous improvement.

  • Establish clear performance expectations, build organizational capabilities, and create growth opportunities that support both individual development and long-term business success.

Required Qualifications:

Leadership & Strategic Influence

  • You will have 10+ years of progressive leadership experience in sales enablement, sales leadership, strategic marketing, communications, business consulting, or related functions.

  • Proven success leading high-performing teams and driving results in complex, highly matrixed organizations.

  • Exceptional executive communication, interpersonal, and stakeholder management skills, with the ability to influence and align leaders across all levels of the organization.

  • Demonstrated ability to mentor, coach, and develop team members while fostering a culture of accountability, collaboration, and continuous improvement.

Strategy, Enablement & Business Execution

  • Experience partnering with sales, marketing, product, and business leaders to translate strategy into actionable programs and measurable business outcomes.

  • Proven ability to lead strategic initiatives, sales activation efforts, organizational change, and cross-functional projects from concept through execution.

  • Experience developing value propositions, sales enablement programs, communications strategies, and client-facing content that drive field engagement and business impact.

  • Strong business acumen and strategic thinking skills, with the ability to connect organizational priorities to market execution.

Operational Excellence

  • Strong organizational and project leadership skills, with the ability to prioritize and manage multiple complex initiatives in a fast-paced environment.

  • Meticulous attention to detail and commitment to delivering high-quality work products and experiences.

  • Proven ability to proactively identify risks, solve problems, and address potential obstacles before they impact delivery or business outcomes.

  • Demonstrated ability to balance strategic thinking with operational execution, ensuring consistent delivery against objectives.

Personal Effectiveness

  • Self-starter with strong ownership, accountability, and follow-through.

  • Growth mindset with a willingness to challenge the status quo, embrace innovation, and continuously improve processes, capabilities, and business results.

Pay Range

The typical pay range for this role is:

$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. 
 

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: 11/25/2026

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

CVS Health Boston, Massachusetts, USA Office

Boston, Massachusetts, United States, 02114

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