Senior Director, Product Strategy

📍 Job Overview

Job Title: Senior Director, Product Strategy

Company: Cigna Healthcare

Location: Connecticut, United States (Work at Home)

Job Type: FULL_TIME

Category: Product Strategy & Management / Operations Leadership

Date Posted: 2026-06-24

Experience Level: Senior Level (10+ years)

Remote Status: Fully Remote (United States)

🚀 Role Summary

• Define and execute enterprise-level digital product strategy and roadmaps for a complex healthcare portfolio, impacting Express Scripts PBS, Express Scripts, EnGuide Pharmacy, Evernorth, and Accredo.

• Lead the end-to-end digital product experience, ensuring consistency and quality across integrated, cross-channel customer touchpoints and interactions.

• Drive value-based prioritization of digital product investments using data insights and a test-and-learn approach to optimize performance and customer outcomes.

• Serve as a strategic enterprise leader and influencer, aligning diverse stakeholders and navigating complex organizational dynamics to achieve unified product vision and execution.

• Champion the adoption of AI and disruptive technologies, staying ahead of industry trends to foster innovation and deliver differentiated digital experiences.

📝 Enhancement Note: This role is positioned as a Senior Director, indicating a significant leadership capacity with enterprise-wide strategic influence. The focus on "end-to-end digital product strategy" across multiple business units (Express Scripts, Evernorth, Accredo) suggests a need for strong operations alignment, process integration, and cross-functional leadership skills to ensure seamless execution and value delivery within a complex healthcare ecosystem. The emphasis on AI and innovation implies a forward-thinking approach to product development and operational efficiency.

📈 Primary Responsibilities

• Establish and articulate a clear, enterprise-level digital product vision and long-term roadmap, translating broad business priorities into actionable product strategies and delivery plans.

• Drive alignment of product strategy across multiple product teams, engineering, design, engagement, platform, data, and business leadership groups to ensure cohesive execution.

• Own the strategy and execution of integrated, cross-channel digital experiences, ensuring consistency and quality across all customer touchpoints and product interactions.

• Lead value-based prioritization of product investments by analyzing business impact, customer outcomes, and data insights, championing a test, learn, and scale mindset.

• Serve as a strategic leader and influencer, aligning stakeholders around a unified product strategy while maintaining clear accountability for digital product outcomes and execution within a complex, highly matrixed environment.

• Drive best-in-class use of AI and disruptive technologies at pace, synthesizing competitive and industry trends, emerging digital capabilities, and voice-of-the-customer insights into prioritization and design decisions.

• Build, lead, and develop high-performing digital product teams, including product leaders and product owners responsible for web and mobile experiences, fostering a culture of accountability, innovation, and continuous improvement.

• Leverage analytics and data-driven insights to identify opportunities, measure product performance, optimize outcomes, and ensure product strategies are grounded in measurable business and customer value.

• Partner closely with product, engineering, design, content, analytics, and operations teams to deliver cohesive solutions and ensure seamless coordination across teams for end-to-end value delivery.

📝 Enhancement Note: The responsibilities highlight a critical need for operational excellence in product delivery. The emphasis on "cross-functional integration," "data-driven decision making," and "enterprise leadership" points to a role that bridges strategy and execution, requiring strong process management, stakeholder alignment, and performance measurement capabilities. The mention of "operations teams" in the responsibilities suggests direct collaboration on process implementation and optimization.

🎓 Skills & Qualifications

Education: Bachelor's degree in Business, Computer Science, Engineering, or a related field. Master's degree or MBA preferred.

Experience:

• 10+ years of progressive experience in digital product management and strategy, with a significant portion focused within the healthcare industry.

• Demonstrated track record of building and scaling product organizations, not just managing existing teams, showcasing leadership in growth and development.

• Proven experience leading web and mobile product portfolios and delivering integrated, omnichannel digital experiences.

• Experience operating in complex, highly matrixed organizational environments with multiple stakeholders and competing priorities. Required Skills:

• Product Strategy & Vision: Ability to define and articulate a clear, enterprise-level product vision and long-term roadmap.

• Digital Product Management: Deep expertise in managing digital products, including web and mobile platforms, with a focus on customer experience.

• Omnichannel Experience Design: Proven ability to create and deliver integrated, cross-channel digital experiences that are consistent and high-quality.

• Stakeholder Management & Influence: Demonstrated ability to influence senior executives, drive enterprise-wide alignment, and navigate complex organizational dynamics.

• Data-Driven Decision Making: Strong expertise in leveraging analytics to identify opportunities, measure performance, and optimize outcomes, grounding strategies in measurable value.

• Team Leadership & Talent Development: Experience building, leading, and developing high-performing product teams and leaders, fostering a culture of accountability and innovation.

• Healthcare Industry Knowledge: Proven experience leading digital product strategy within healthcare, with a strong focus on patient and customer communication experiences.

• AI & Innovation: Strong understanding of emerging digital channels and technologies, with experience deploying innovative capabilities and AI at scale.

Preferred Skills:

• Agile Methodologies: Proficiency in Agile, Scrum, or other iterative development frameworks for product delivery.

• User Experience (UX) Principles: Understanding of UX best practices to ensure intuitive and effective digital products.

• Market Analysis & Competitive Intelligence: Ability to conduct thorough market analysis and competitive intelligence to inform product strategy.

• Financial Acumen: Understanding of financial modeling and ROI analysis for product investments.

📝 Enhancement Note: The "scaling product organizations" requirement implies a need for candidates who understand the operational build-out of product functions, including process definition, team structure, and resource allocation. The emphasis on healthcare product strategy specifically points to experience with regulatory environments, patient journeys, and health-related data considerations.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Product Strategy & Roadmap Examples: Showcase comprehensive examples of enterprise-level product strategies and roadmaps developed, including how they translated business priorities into actionable plans.

• Integrated Digital Experience Case Studies: Present case studies demonstrating the successful design and delivery of integrated, cross-channel digital experiences, highlighting complexity and scale.

• Value-Based Prioritization Frameworks: Illustrate frameworks or methodologies used for value-based prioritization of product investments, detailing how data insights and customer outcomes were incorporated.

• AI/Innovation Implementation Projects: Provide examples of projects where AI or other disruptive technologies were successfully implemented at scale, demonstrating innovation and measurable impact.

Process Documentation:

• Product Lifecycle Management: Documentation of processes for managing the entire product lifecycle, from ideation and strategy through development, launch, and ongoing optimization.

• Cross-Functional Collaboration Workflows: Examples of established workflows and processes that facilitate seamless collaboration between product, engineering, design, data, and operations teams.

• Data-Driven Decision Making Processes: Evidence of structured processes for leveraging analytics and data insights to inform product strategy, prioritization, and performance measurement.

• Agile/Scrum Implementation Documentation: If applicable, documentation outlining the implementation and adherence to Agile or Scrum methodologies for product development and delivery.

📝 Enhancement Note: For a Senior Director role, the portfolio should demonstrate strategic thinking and operational execution at an enterprise level. Candidates should be prepared to showcase not just what they achieved, but how they achieved it, emphasizing the processes, methodologies, and cross-functional collaboration that underpinned their success. This includes demonstrating an understanding of how to build and scale product operations.

💵 Compensation & Benefits

Salary Range: $183,500 - $305,800 USD (Annual)

Benefits:

• Comprehensive Health Coverage: Medical, vision, dental insurance, along with dedicated well-being and behavioral health programs.

• Retirement Savings: 401(k) plan with company contributions.

• Life Insurance: Company-paid life insurance policy.

• Professional Development: Tuition reimbursement for continued education and skill enhancement.

• Generous Paid Time Off: A minimum of 18 days of paid time off per year, plus paid holidays.

• Leave of Absence: Access to leaves of absence for various needs.

Working Hours: Standard full-time hours (estimated 40 hours per week), with potential for flexibility given the remote nature of the role and the need for effective global collaboration.

📝 Enhancement Note: The salary range is provided by the employer. The range is substantial and reflects a senior leadership position with significant responsibility. The benefits package is comprehensive, emphasizing employee well-being and professional growth, which are often key attractors for senior operations and strategy roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare and Health Services (specifically within health insurance, pharmacy benefit management, and health services). Cigna Healthcare operates within a highly regulated and competitive landscape, prioritizing innovation, customer-centricity, and operational efficiency.

Company Size: The Cigna Group is a large, publicly traded company (indicated by its scale and broad offerings across Cigna Healthcare and Evernorth Health Services). This means the operations team likely operates within a structured environment with established processes, but also has the resources for significant investment in technology and talent.

Founded: The Cigna Group has a long history, tracing roots back to the 18th century. This rich history suggests a stable, established organization with a deep understanding of the healthcare market, while also being committed to modernizing its digital offerings.

Team Structure:

• Product Organization: This role sits within a broader digital product organization, likely comprising multiple product teams, product owners, designers, and engineers.

• Reporting Structure: The Senior Director will likely report to a VP or SVP of Digital Product or Digital Transformation, overseeing a team of product leaders and individual contributors.

• Cross-Functional Collaboration: Expect extensive collaboration with engineering, design, marketing, data analytics, operations, legal, compliance, and various business unit leaders across Express Scripts, Evernorth, and Accredo.

Methodology:

• Data-Driven Operations: Emphasis on leveraging data analytics and insights to inform product strategy, measure performance, and drive continuous improvement in digital product offerings.

• Agile & Iterative Development: Likely utilizes Agile methodologies for product development, fostering flexibility, rapid iteration, and a test-and-learn approach.

• Customer-Centric Design: A strong focus on understanding and meeting the needs of patients, customers, and stakeholders through user-centered design principles.

Company Website: https://www.thecignagroup.com/

📝 Enhancement Note: The company's positioning across multiple healthcare segments (insurance, pharmacy, health services) indicates a complex operational environment. The Senior Director will need to understand how digital products integrate across these distinct but related areas, requiring strong GTM strategy alignment and operational process harmonization.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Director role, placing it at a high-level leadership position within the product strategy function. It signifies substantial responsibility for strategic direction, team management, and enterprise-wide impact. This level typically involves significant autonomy and accountability for achieving key business objectives through digital product innovation and execution.

Reporting Structure: The Senior Director will likely report to a Vice President or Senior Vice President of Digital Strategy, Product, or Transformation. They will be responsible for leading and developing a team of Product Managers, Product Owners, and potentially other strategy professionals, who in turn manage specific product portfolios or initiatives.

Operations Impact: This role has a direct and significant impact on Cigna Healthcare's revenue and business decisions by defining the digital product strategy that shapes customer engagement, service delivery, and operational efficiency across major business units like Express Scripts and Evernorth. Success in this role directly influences customer acquisition, retention, satisfaction, and ultimately, profitability through optimized digital experiences and innovative solutions.

Growth Opportunities:

• Executive Leadership Path: Potential to advance to VP or SVP roles within Digital Product, Strategy, or broader Digital Transformation functions, overseeing larger portfolios or entire business units.

• Specialization & Deepening Expertise: Opportunities to become a recognized leader in specific areas, such as AI in healthcare products, omnichannel customer journeys, or digital health innovation.

• Cross-Functional Leadership Roles: The experience gained in navigating complex matrixed organizations and aligning diverse stakeholders can prepare individuals for broader leadership roles in areas like GTM strategy, business operations, or innovation labs.

• Mentorship & Team Development: A key growth area will be in developing and mentoring other product leaders, contributing to the overall talent pipeline within Cigna Healthcare.

📝 Enhancement Note: The growth trajectory for a Senior Director in Product Strategy within a large healthcare organization is typically towards broader strategic leadership. For individuals with a background in operations, this role offers a pathway to influence operational strategy through product innovation, bridging the gap between technical product development and business process execution.

🌐 Work Environment

Office Type: This is a remote position, allowing employees to work from home within the United States. The company emphasizes that a cable broadband or fiber optic internet connection with at least 10Mbps download/5Mbps upload is required for effective work.

Office Location(s): While the role is remote, the company headquarters are in Connecticut, USA. The remote work authorization is for the United States, suggesting that employees must reside and perform their duties within the US.

Workspace Context:

• Independent Work Environment: Employees are expected to maintain a productive home office environment conducive to focus and concentration.

• Digital Collaboration Tools: Extensive use of digital collaboration platforms (e.g., Microsoft Teams, Slack, Zoom, project management software) will be essential for team communication, meetings, and project tracking.

• Access to Technology: The company provides the necessary digital infrastructure and tools for remote work, but employees are responsible for ensuring a reliable internet connection.

Work Schedule: While standard full-time hours (estimated 40 hours per week) are expected, the remote nature of the role may offer some flexibility. However, given the enterprise leadership scope and the need to coordinate with various teams across different time zones and business units, a significant commitment to availability, especially during core business hours and for key meetings, will be necessary.

📝 Enhancement Note: The remote-first nature of this role underscores the importance of strong self-management, proactive communication, and proficiency with remote collaboration tools. For operations professionals, this means being adept at managing workflows and stakeholder relationships without the benefit of in-person proximity.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will likely conduct an initial phone screen to assess basic qualifications, experience, and alignment with the role's core requirements.

• Hiring Manager Interview: A deeper dive into your experience with product strategy, leadership, healthcare, and digital transformation. Be prepared to discuss your approach to defining vision, roadmaps, and driving alignment.

• Panel Interviews: Expect to meet with a panel of stakeholders, including cross-functional leaders from product, engineering, design, and potentially business unit representatives. These interviews will focus on your collaboration style, problem-solving abilities, and how you handle complex organizational challenges.

• Portfolio Presentation: A critical stage will involve presenting a portfolio of your work, showcasing strategic initiatives, product roadmaps, successful digital experience implementations, and how you've driven measurable outcomes.

• Executive Interview: A final interview with a senior executive (e.g., VP/SVP) to assess strategic fit, leadership potential, and overall alignment with Cigna Healthcare's vision.

Portfolio Review Tips:

• Showcase Strategic Impact: Focus on how your product strategies directly contributed to business goals, customer outcomes, and operational efficiencies. Quantify results wherever possible.

• Demonstrate Process & Methodology: Explain the processes you followed, the methodologies you employed (e.g., Agile, data-driven decision-making), and how you managed cross-functional collaboration.

• Highlight Leadership & Scaling: Provide examples of how you built or scaled product teams and organizations, demonstrating your ability to lead and develop talent.

• Address Complexity: Use case studies that illustrate your ability to navigate complex, matrixed environments and align multiple stakeholders around a unified vision.

• Focus on Healthcare Relevance: Tailor examples to showcase your understanding of the healthcare industry, patient journeys, and customer communication challenges.

Challenge Preparation:

• Product Strategy Case Study: Be prepared to discuss a hypothetical or past product strategy challenge, outlining your approach to problem definition, analysis, solution design, prioritization, and execution.

• Leadership Scenarios: Anticipate questions about how you would handle team conflicts, drive alignment among resistant stakeholders, or manage underperforming product initiatives.

• Innovation & AI Discussion: Be ready to discuss your perspective on the role of AI and emerging technologies in healthcare product strategy and how you would foster innovation within a large organization.

📝 Enhancement Note: The emphasis on "portfolio presentation" and "challenge preparation" suggests the company values tangible evidence of strategic thinking and operational execution. Candidates should prepare to articulate their thought processes and demonstrate how they drive measurable results through structured approaches.

🛠 Tools & Technology Stack

Primary Tools:

• Product Management Platforms: Tools like Jira, Confluence, Aha!, Productboard for roadmap planning, backlog management, and documentation.

• Collaboration Suites: Microsoft 365 (Teams, SharePoint, Office Suite) or Google Workspace for daily communication, document sharing, and project management.

• Analytics & BI Tools: Adobe Analytics, Google Analytics, Tableau, Power BI, or similar platforms for data analysis, performance tracking, and dashboard creation.

• CRM Systems: Salesforce or similar CRM platforms may be relevant for understanding customer segmentation and engagement data.

• Prototyping & Design Tools: Figma, Sketch, Adobe XD for reviewing and understanding design outputs and user flows.

Analytics & Reporting:

• Web Analytics: Tools to track user behavior, conversion rates, and engagement metrics on web and mobile platforms.

• Data Warehousing & ETL Tools: Understanding of how data is sourced, transformed, and made available for analysis.

• Business Intelligence (BI) Dashboards: Proficiency in interpreting and creating dashboards to communicate key performance indicators (KPIs) to stakeholders.

CRM & Automation:

• Customer Data Platforms (CDP): Potentially used for unifying customer data across various touchpoints.

• Marketing Automation Platforms: Tools for customer outreach and engagement, though less direct for this role, understanding their integration is beneficial.

• API & Integration Concepts: Familiarity with how different systems (CRM, analytics, product platforms) integrate to provide a holistic view.

📝 Enhancement Note: While this role is strategic, a strong understanding of the underlying technology stack and how different tools support product development, data analysis, and cross-functional operations is crucial. The ability to leverage these tools for insights and to communicate effectively with technical teams is a key differentiator.

👥 Team Culture & Values

Operations Values:

• Customer Centricity: A deep commitment to understanding and serving the needs of patients and customers, ensuring digital products deliver exceptional value and experience.

• Data-Driven Innovation: A culture that encourages the use of data and analytics to drive strategic decisions, measure impact, and foster continuous innovation in product development.

• Accountability & Ownership: A strong sense of responsibility for outcomes, with individuals and teams owning their contributions and driving initiatives to successful completion.

• Collaboration & Partnership: Emphasis on working effectively across diverse teams and business units, fostering strong partnerships to achieve shared goals and drive enterprise-wide alignment.

• Agility & Adaptability: A mindset that embraces change, learns from experimentation, and adapts quickly to evolving market dynamics and technological advancements.

Collaboration Style:

• Cross-Functional Integration: The team embraces a collaborative style where product, engineering, design, data, and operations work in tight-knit, integrated teams to deliver cohesive solutions.

• Open Communication & Feedback: A culture that encourages open dialogue, constructive feedback, and knowledge sharing to drive continuous improvement and problem-solving.

• Strategic Alignment Focus: Collaboration is driven by a shared understanding of the enterprise strategy and a collective effort to align priorities and execution across different functions and business units.

📝 Enhancement Note: The company values suggest a dynamic and collaborative environment where strategic thinking is paired with a commitment to measurable results and customer well-being. For operations professionals, this means demonstrating an ability to translate strategic vision into actionable processes and to collaborate effectively to achieve those goals.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Complex Matrixed Organizations: Effectively aligning product strategy and execution across multiple distinct business units (Express Scripts, Evernorth, Accredo) with potentially different priorities and operational models.

• Driving Enterprise-Wide AI Adoption: Championing and integrating AI and disruptive technologies at scale across a large, established organization, requiring change management and overcoming potential resistance.

• Balancing Innovation with Execution: Ensuring that the pursuit of new digital capabilities and innovative solutions does not detract from the consistent delivery and operational excellence of existing product portfolios.

• Maintaining Data Privacy & Security: Operating within the highly regulated healthcare industry requires stringent adherence to data privacy (e.g., HIPAA) and security protocols in all product development and deployment efforts.

Learning & Development Opportunities:

• Advanced Product Strategy: Deepen expertise in strategic planning, market analysis, and competitive landscaping within the evolving healthcare tech sector.

• AI & Emerging Technologies: Opportunities to lead the charge in applying cutting-edge AI and machine learning to solve complex healthcare challenges and improve customer experiences.

• Leadership Development: Access to executive coaching, leadership training programs, and mentorship to enhance strategic leadership and talent management skills.

• Industry Exposure: Participation in industry conferences, workshops, and forums to stay abreast of best practices, emerging trends, and network with peers in digital health and product management.

📝 Enhancement Note: The challenges highlight the need for strong operational leadership skills, particularly in change management, process integration, and risk mitigation within a regulated environment. The growth opportunities point towards a career path focused on executive-level influence and specialization in digital health innovation.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you developed an enterprise-level product strategy for a complex organization. What was your process, who did you involve, and what were the key outcomes?" (Focus on your strategic thinking, cross-functional alignment, and impact measurement.)

• "How would you approach prioritizing digital product investments across multiple business units with competing needs, ensuring alignment with overall enterprise goals?" (Prepare to discuss your frameworks for value-based prioritization, data analysis, and stakeholder negotiation.)

• "Walk us through your experience leading the integration of AI or other disruptive technologies into product roadmaps. What were the challenges, and how did you drive adoption and measure success?" (Highlight your innovation mindset, technical understanding, and ability to translate new tech into business value.) Company & Culture Questions:

• "What do you know about Cigna Healthcare and its various divisions (Express Scripts, Evernorth, Accredo), and how do you see digital product strategy playing a role in their success?" (Research the company's recent news, strategic initiatives, and market position.)

• "How would you foster a culture of innovation and continuous improvement within a large, distributed product team?" (Discuss your leadership style, team-building strategies, and approaches to driving change.)

• "Describe a situation where you had to influence senior executives to gain buy-in for a strategic product initiative. What methods did you use, and what was the result?" (Focus on your communication, influencing, and executive presence skills.) Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the business problem, your strategic approach, the operational processes you leveraged or established, the team collaboration involved, the key decisions made, and the quantifiable results achieved.

• Quantify Impact: Wherever possible, use metrics to demonstrate the success of your initiatives (e.g., increased customer engagement by X%, reduced operational costs by Y%, improved conversion rates by Z%).

• Highlight Operational Excellence: Emphasize how your strategies were supported by robust operational processes, effective cross-functional collaboration, and data-driven decision-making.

• Tailor to Cigna: Connect your experience and examples to Cigna's specific business units and the healthcare industry's unique challenges and opportunities.

• Be Prepared for Q&A: Anticipate detailed questions about your decision-making process, the challenges you faced, and how you would apply your learnings to Cigna's context.

📝 Enhancement Note: The interview questions are designed to assess strategic depth, leadership capability, operational acumen, and cultural fit. Candidates should prepare to articulate their experience using the STAR method (Situation, Task, Action, Result) and to demonstrate a clear understanding of how product strategy drives operational efficiency and business growth.

📌 Application Steps

To apply for this Senior Director, Product Strategy position:

• Submit your application through the provided Workday link.

• Curate Your Portfolio: Select 2-3 of your most impactful projects that best demonstrate your experience in enterprise product strategy, digital transformation, cross-functional leadership, and driving measurable outcomes within complex organizations, ideally in healthcare.

• Optimize Your Resume: Ensure your resume clearly highlights leadership experience, strategic accomplishments, relevant technical skills (e.g., AI, data analytics), and any experience scaling product organizations or managing complex portfolios. Use keywords from the job description.

• Prepare Your Narrative: Practice articulating your portfolio case studies concisely, focusing on the strategic rationale, operational execution, collaborative efforts, and quantifiable results. Be ready to discuss your leadership philosophy and approach to innovation.

• Research Cigna Healthcare: Gain a deep understanding of Cigna's various business units (Cigna Healthcare, Express Scripts, Evernorth, Accredo), their market position, strategic priorities, and any recent digital initiatives. This will help you tailor your responses and demonstrate genuine interest.

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