Senior Manager, Digital Product Strategy at CVS Health

📍 Job Overview

Job Title: Senior Manager, Digital Product Strategy

Company: CVS Health

Location: Chicago, Illinois, United States

Job Type: FULL_TIME

Category: Product Strategy / Digital Product Management

Date Posted: 2025-06-09T00:00:00

Experience Level: 7+ years (Senior Manager)

Remote Status: On-site / Hybrid / Telecommute (Chicago, IL preferred, with remote options in OK, PA)

🎨 Role Summary

Lead the strategic development and enhancement of digital products and services specifically for CVS Caremark Members, applying expertise in user-centric design and agile methodologies.
Drive the digital product roadmap, focusing on prioritization and successful delivery to enhance brand recognition and competitive advantage in the healthcare industry.
Conduct comprehensive market research and complex data analysis (qualitative and quantitative) to inform product features, influence prioritization, and ensure digital products meet evolving customer needs and expectations.
Champion cross-functional collaboration with design, engineering, marketing, content strategy, and PR teams to ensure seamless product development, deployment, and launch.
Apply strong storytelling and presentation skills to communicate product vision, roadmaps, and insights to stakeholders at all organizational levels.
Mentor and coach team members within the digital product strategy function, fostering a growth mindset and execution excellence.

📝 Enhancement Note: While the core role is Product Strategy, the emphasis on "digital products," "user-centric design," "user experiences," and collaboration with design teams strongly implies a need for a deep understanding of design principles, methodologies, and their integration into the product lifecycle. The candidate will likely be expected to effectively collaborate with and guide design teams.

🖼️ Primary Responsibilities

Prioritize and manage the digital product roadmap, ensuring alignment with company goals and market demands, specifically focusing on enhancing the member experience for Caremark.
Develop and maintain technology and product roadmaps, identifying potential risks and improvement opportunities to proactively manage the digital product portfolio.
Generate and evaluate innovative digital product ideas that integrate seamlessly with existing technology while adhering to healthcare regulatory, safety, quality, and confidentiality standards.
Perform detailed analysis of qualitative and quantitative data to derive actionable insights that directly influence product feature development and strategic prioritization decisions.
Define key performance indicators (KPIs) and success metrics for digital products, continuously monitoring analytics, competitive landscape shifts, and evolving customer needs to refine product strategy.
Coordinate closely with Marketing, Content Strategy, and Public Relations teams to plan and execute successful go-to-market strategies and launches for new digital products and services.
Facilitate continuous and effective communication and collaboration across various functional units and stakeholder groups, building strong relationships at all levels of the organization.
Provide leadership, mentorship, and coaching to team members, fostering professional growth and skill development within the digital product team.
Oversee and approve product iterations, release schedules, and roadmaps to maintain a rapid pace of innovation and market differentiation.
Contribute to the annual budget planning process, identifying digital product needs and aligning resource allocation with overall company revenue and profitability targets.

📝 Enhancement Note: The responsibilities highlight the strategic nature of the role, focusing on roadmap ownership, innovation, data analysis, and significant cross-functional leadership. For a design professional considering this role, understanding how their design expertise informs and drives these strategic decisions will be crucial.

🎓 Skills & Qualifications

Education: A Bachelor's degree is preferred, ideally in a related field such as Business, Marketing, Design, Computer Science, or a relevant professional qualification. Specialized training in product management, user experience, or agile methodologies would be beneficial.

Experience: Minimum of 7+ years of progressive work experience, with a significant portion focused on digital product strategy, product management, or a closely related field within a complex organizational environment. Experience leading product teams and a strong portfolio demonstrating strategic thinking and impactful product outcomes are highly valued.

Required Skills:

Extensive experience in Digital Product Strategy, including roadmap development, prioritization, and execution.
Proficiency in conducting Market Research and competitive analysis to identify opportunities and inform product decisions.
Strong understanding of User-Centric Design principles and the importance of user experience in digital product development.
Demonstrated expertise in Agile Methodologies and product development lifecycle management.
Excellent Collaboration and teamwork skills, with the ability to work effectively across diverse functional teams (design, engineering, marketing, etc.).
Proven Problem Solving and Decision Making abilities in a fast-paced and complex environment.
Adept at Business Intelligence and leveraging data analytics to drive product strategy and measure success.
Strong Storytelling and Presentation Skills, capable of effectively communicating complex ideas and product vision to various audiences.

Preferred Skills:

Experience in Management Consulting, particularly within the healthcare or digital technology sectors.
Demonstrated success in leading and collaborating with Multi-Disciplinary Product Teams, including design, engineering, and research professionals.
Experience in the healthcare or pharmacy benefits management industry (relevant to Caremark focus).
Familiarity with Design Thinking methodologies and their application in product strategy.
Experience with user research, usability testing, and incorporating user feedback into product iterations.

📝 Enhancement Note: While not a pure design role, the emphasis on user-centric design and collaboration with design teams means a strong understanding of the design process and its strategic impact is essential. Candidates with a design background looking to move into product strategy should highlight their strategic thinking, business acumen, and ability to translate user needs into product requirements.

🎨 Portfolio & Creative Requirements

Portfolio Essentials:

While a traditional visual design portfolio might not be the primary requirement, candidates should be prepared to present case studies or examples that demonstrate their strategic thinking and impact on digital product outcomes. Focus on the "why" and "how" behind product decisions.
Case studies should clearly articulate the problem addressed, the market opportunity identified, the strategic approach taken, the key design and product decisions made (and why), and the resulting business and user impact (using metrics).
Highlight projects where you successfully collaborated with design teams, demonstrating your understanding of the design process and your ability to leverage design to achieve product goals.
Showcase your analytical skills by presenting data-driven insights that informed your product strategy and decisions.

Process Documentation:

Be prepared to discuss your approach to market research and user discovery, outlining the methodologies used to understand user needs and market trends.
Explain your process for ideation, strategic planning, and roadmapping, including how you prioritize features and manage trade-offs within an agile framework.
Describe your approach to product validation and testing, including how you gather user feedback and iterate on digital products based on performance data.

📝 Enhancement Note: Since this is a strategy role with a focus on digital products and user experience, the portfolio requirement shifts from visual execution to demonstrating strategic thinking, problem-solving, and the ability to drive impactful product outcomes through effective collaboration with design and other teams.

💵 Compensation & Benefits

Salary Range: $130,295.00 - $260,590.00 per year.

📝 Enhancement Note: The provided salary range is exceptionally wide, suggesting it covers various factors including experience, specific skill sets, and potentially location within the approved remote states (Oklahoma and Pennsylvania) compared to the preferred Chicago location. The actual offer will likely be influenced by the candidate's proven track record in digital product strategy, experience in the healthcare sector, and leadership capabilities.

Benefits:

Comprehensive Medical Plan Options to support your health and well-being.
401(k) Plan with matching company contributions to help you save for retirement.
Employee Stock Purchase Plan, providing an opportunity to invest in the company's future.
No-cost Wellness Screenings, Tobacco Cessation, and Weight Management Programs to support a healthy lifestyle.
Confidential Counseling and Financial Coaching services for personal and financial support.
Generous Paid Time Off and Flexible Work Schedules to promote work-life balance.
Family Leave and Dependent Care Resources to support family needs.
Colleague Assistance Programs and Tuition Assistance for professional development.
Retiree Medical Access depending on eligibility.

Working Hours: This is a full-time position, typically requiring around 40 hours per week. The nature of a Senior Manager role may necessitate flexibility based on project deadlines and team needs, particularly given the remote work options in some locations.

🎯Team & Company Context

🏢 Company & Design Culture

Industry: CVS Health operates within the Hospitals and Health Care industry, specifically focusing on Retail, Pharmacy Benefits Management, Health Insurance, and Care Management. This context means digital products must navigate complex regulatory environments while prioritizing patient and member needs.

Company Size: CVS Health is a very large organization with over 300,000 colleagues globally (10,001+ on LinkedIn). Working within such a large company means navigating complex organizational structures, collaborating with numerous stakeholders, and influencing decisions across various business units. For design professionals, this implies the need for strong communication, negotiation, and the ability to advocate for user needs within a large enterprise.

Founded: Founded in 1963, CVS Health has a long history and is a well-established player in the healthcare market. This history shapes the company's culture, potentially influencing its approach to innovation and digital transformation.

Team Structure:

The digital product strategy team likely sits within a larger digital or technology organization.
As a Senior Manager, you would likely lead a team of product strategists or product managers, reporting to a Director or VP-level leader.
Significant cross-functional collaboration is expected with design teams (UI/UX), engineering, clinical teams, legal/compliance, marketing, and operations.

Methodology:

The job description mentions "agile methodologies," suggesting teams likely work in sprints, with iterative development and continuous feedback loops.
A strong emphasis on user-centric design implies the incorporation of user research, prototyping, and usability testing within the product development process.
Data analysis and business intelligence are key components, indicating a data-driven approach to product decision-making.

Company Website: CVSHealth.com

📝 Enhancement Note: Given CVS Health's size and industry, the design culture likely emphasizes user-centered design within a framework of regulatory compliance and business objectives. Collaboration and the ability to influence across a large organization will be critical for success in this role, even for those with a strong design background transitioning into strategy.

📈 Career & Growth Analysis

Design Career Level: This role is at a Senior Manager level, which in a large organization like CVS Health signifies a position of significant responsibility, requiring not only strategic thinking but also leadership and team management capabilities. It is a step up from individual contributor roles and often involves managing a team or leading complex initiatives.

Reporting Structure: The Senior Manager likely reports to a Director or Vice President within the Digital Product organization, providing a clear path for growth into higher leadership roles. The role involves managing direct reports and influencing peers and senior leaders.

Design Impact: While not a hands-on design role, this position has a significant impact on the design of digital products by defining the strategy, prioritizing features, and ensuring that user needs are at the forefront of product development. Success requires effectively partnering with design teams to translate strategic goals into compelling user experiences.

Growth Opportunities:

Advancement to Director or VP-level roles within Digital Product Management or Strategy.
Opportunities to lead larger or more complex product portfolios across different areas of CVS Health.
Development of leadership skills, including team management, mentoring, and strategic planning at a higher level.
Increased influence on the overall digital transformation strategy of a major healthcare company.

📝 Enhancement Note: For design professionals aspiring to move into product leadership, this role offers a clear pathway by leveraging design thinking and user-centric expertise within a strategic context. Highlighting leadership potential and strategic impact in their portfolio and interviews will be crucial.

🌐 Work Environment

Studio Type: The primary location is listed as the Chicago office, suggesting an on-site or hybrid work environment is preferred for this location. However, remote options are available in Oklahoma and Pennsylvania, indicating flexibility depending on the candidate's location and potentially team structure.

Office Location(s): The main office address is in Chicago, IL (333 W Wacker Dr). The job also lists remote options in "Work At Home-Oklahoma" and "Work At Home-Pennsylvania."

Design Workspace Context:

For the Chicago location, expect a corporate office environment with dedicated workspaces and meeting rooms. The setup likely supports collaboration with cross-functional teams, including potentially co-located design and engineering teams.
Remote locations would involve working from home, requiring self-discipline and effective remote collaboration tools and practices.
Regardless of location, the role requires significant interaction with design, engineering, and business teams, necessitating comfort with virtual collaboration platforms.

Work Schedule: This is a full-time role, generally following standard business hours. However, as a Senior Manager, there may be instances requiring flexibility to accommodate meetings across different time zones (if collaborating with teams in other locations) or to meet project deadlines.

📝 Enhancement Note: The hybrid/remote nature of the role requires candidates to be proficient in both in-person and virtual collaboration. For design professionals, this means being able to effectively communicate design vision, provide feedback, and collaborate on strategic decisions using digital tools.

📄 Application & Portfolio Review Process

Design Interview Process:

Initial Screening: Expect a recruiter screen to assess basic qualifications and experience, including relevant digital product strategy and leadership experience. Be prepared to briefly articulate your strategic approach and career goals.
Hiring Manager Interview: This will likely focus on your experience leading product strategy, managing teams, and collaborating with cross-functional partners (including design). Be ready to discuss specific examples of successful product initiatives you've led and how you've incorporated user-centric principles.
Panel Interviews: You may interview with various stakeholders, including potentially design leadership, engineering managers, and business leaders. These interviews will assess your ability to collaborate effectively across different disciplines and influence strategic decisions. Be prepared to discuss how you partner with design teams to achieve product outcomes.
Case Study or Presentation: You might be asked to prepare and present a case study of a digital product strategy you developed or a strategic problem you solved. Focus on your process, data-driven insights, and the impact of your decisions. If applicable, highlight how design contributed to the success.
Final Interviews: These may involve senior leadership, focusing on your strategic vision, leadership potential, and fit within the company culture.

Portfolio Review Tips:

As this is a strategy role, your "portfolio" should emphasize strategic outcomes and your process rather than just visual design. Prepare case studies that detail the business problem, market opportunity, your strategic approach, key decisions, and measurable results.
For each case study, clearly articulate your role and how you collaborated with design and other teams. Highlight instances where you championed user needs and leveraged design insights to inform strategy.
Focus on the impact of your work, using data and metrics to demonstrate success. Quantify outcomes whenever possible (e.g., increased user engagement, improved conversion rates, cost savings).
Structure your case studies to tell a compelling story, outlining the challenge, your approach, and the results.

Challenge Preparation:

If a case study or presentation is required, choose a project that demonstrates your strategic thinking, problem-solving skills, and ability to drive results in a complex environment.
Practice presenting your case study clearly and concisely, focusing on the strategic rationale and impact. Be prepared to answer questions about your decision-making process and collaboration style.
If given a specific problem to solve as a challenge, approach it systematically. Outline your process for understanding the problem, conducting research, developing a strategic approach, and proposing solutions. Consider how design would be integral to the solution.

ATS Keywords: Digital Product Strategy, Product Management, User-Centric Design, Agile Methodologies, Market Research, Collaboration, Problem Solving, Decision Making, Business Intelligence, Storytelling, Presentation Skills, Mentoring, Coaching, Data Analysis, Cross-Functional Coordination, Innovation, Regulatory Compliance, Healthcare, Pharmacy Benefits Management, Digital Transformation, Product Roadmap, User Experience, Stakeholder Management, Strategic Planning, Team Leadership, Management Consulting.

📝 Enhancement Note: The interview process will heavily weigh strategic thinking, leadership, and the ability to collaborate effectively across disciplines. For design professionals, demonstrating how their design background informs their strategic approach and ability to partner with design teams will be crucial for success.

🛠 Tools & Technology Stack

Primary Design Tools: While this is not a hands-on design role, familiarity with the tools used by design teams is beneficial for effective collaboration. This might include:

Collaboration Platforms (e.g., Figma, Sketch, Adobe XD) for reviewing design deliverables and providing feedback.
Prototyping Tools (e.g., InVision, Figma) for understanding user flows and interactive designs.
Design System Management Tools for understanding design consistency and scalability.

Collaboration & Handoff:

Project Management Tools (e.g., Jira, Asana, Trello) for tracking product development progress and collaborating with engineering.
Communication Platforms (e.g., Slack, Microsoft Teams) for daily communication and team collaboration.
Documentation Tools (e.g., Confluence) for documenting product requirements, strategies, and decisions.

Research & Testing:

User Research Platforms for gathering user insights and feedback.
Analytics Tools (e.g., Google Analytics, Adobe Analytics, Amplitude) for tracking product performance and user behavior.
A/B Testing Tools for validating product hypotheses and optimizing user experiences.

📝 Enhancement Note: While the candidate won't be using design tools daily, a strong understanding of the design toolchain and workflow will be essential for effective collaboration with design teams and ensuring design quality aligns with strategic goals.

👥 Team Culture & Values

Design Values: While not explicitly stated, based on the job description's emphasis on user-centric design and CVS Health's mission, the design values likely include:

Putting the user (Caremark Member) at the center of all product decisions, focusing on empathy and understanding their needs.
Driving innovation while ensuring accessibility, usability, and a positive user experience across digital platforms.
Collaborating effectively with cross-functional teams to deliver integrated and seamless digital health solutions.
Using data and research to inform design decisions and measure the impact of design on product outcomes.

Collaboration Style:

The job description emphasizes "collaboration and teamwork" and "continuous and cross-communication across functional units." This suggests a highly collaborative environment where effective communication and relationship- building are valued.
Given the size of the organization, navigating a matrix structure and influencing stakeholders without direct authority will be important.
Agile methodologies imply a culture of iterative development, feedback loops, and shared ownership of product outcomes.

📝 Enhancement Note: For candidates from a design background, understanding how their creative approach and user advocacy can thrive within a large, regulated healthcare environment will be key. Highlighting experience in collaborative, cross-functional teams is important.

⚡ Challenges & Growth Opportunities

Design Challenges:

Balancing user needs and design innovation with complex healthcare regulations and compliance requirements.
Navigating a large, complex organization with multiple stakeholders and competing priorities to champion user-centric design and product strategy.
Ensuring seamless and intuitive user experiences across a potentially wide range of digital products and services for Caremark Members.
Staying ahead of evolving digital health trends and technology while maintaining a focus on core user needs and business objectives.

Learning & Development Opportunities:

Opportunities to deepen expertise in digital product strategy within the specialized healthcare domain.
Development of advanced leadership and team management skills in a large corporate setting.
Exposure to complex business challenges and the opportunity to drive significant digital transformation within a major healthcare company.
Potential for attending industry conferences and workshops focused on healthcare technology, digital product management, and user experience in regulated industries.

📝 Enhancement Note: The challenges highlight the need for a strategic leader who can navigate complexity and advocate for user needs within a highly regulated and large organizational environment. The growth opportunities emphasize leadership and strategic impact within the digital health space.

💡 Interview Preparation

Design Process Questions:

Describe your approach to identifying user needs and translating them into product strategy, particularly in a complex domain like healthcare. Be ready to provide examples from your portfolio/case studies.
How do you collaborate with design teams throughout the product lifecycle, from discovery and ideation to testing and iteration? Provide specific examples of successful partnerships.
Discuss a time you had to make a difficult product decision where design and business objectives were in conflict. How did you navigate this, and what was the outcome?

Company Culture Questions:

Based on your understanding of CVS Health and the healthcare industry, what do you believe are the key challenges in designing digital products for Caremark Members?
How do you approach collaboration and influence stakeholders in a large, matrixed organization? Provide examples of how you've built relationships and achieved alignment across different teams.
What does "user-centric design" mean to you in the context of healthcare digital products, and how do you ensure it is prioritized in your product strategy?

Portfolio Presentation Strategy:

For your case studies, focus on telling a compelling story about the problem you solved, your strategic approach, and the impact of your work. Highlight how design was integral to achieving successful outcomes.
Clearly articulate your role and responsibilities in each project, emphasizing your leadership and strategic contributions.
Be prepared to discuss the data and metrics you used to inform your decisions and measure success.
Practice presenting your case studies concisely and engagingly, demonstrating your storytelling and presentation skills.

📝 Enhancement Note: Candidates with a design background should frame their experience and skills in terms of strategic impact, leadership, and their ability to effectively partner with design and other teams to drive product success in a complex healthcare environment.

📌 Application Steps

To apply for this design position:

Submit your application through this link.
Prepare case studies or examples that highlight your strategic thinking, leadership skills, and the impact of your work on digital product outcomes. Focus on the "why" behind your decisions and the results achieved.
Tailor your resume to emphasize your experience in digital product strategy, leadership, collaboration with design teams, and any relevant experience in healthcare or regulated industries. Use relevant ATS keywords.
Research CVS Health, its digital products (especially related to Caremark), and the healthcare industry to demonstrate your understanding of the context and challenges.
Prepare for interviews by practicing articulating your strategic approach, discussing challenging situations, and demonstrating your ability to collaborate effectively across different functions.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and design industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

Senior Manager, Digital Product Strategy