Director IT Agile Practice Management - Medicare

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 seeking an accomplished IT leader to serve as Director, Agile Delivery Practice. This is a high-impact leadership position responsible for overseeing a diverse, strategically important portfolio of technology initiatives and ensuring the highest standards of delivery, governance, and organizational alignment. In this role, you will lead and support multiple, concurrent programs totaling 633,000+ hours of work and representing $44M+ of annual investment. You will be responsible for connecting business strategy to execution, creating structure and predictability in how work gets done, and ensuring that program outcomes translate into tangible value for the enterprise.

Success in this role requires a rare combination of portfolio thinking, hands-on program delivery expertise, and strong stakeholder leadership across technology and business partners.

Required Qualifications

• 10+ years of experience leading Program Managers, Agile/Scrum teams, and cross-functional technology teams, delivering strategic initiatives and business-critical programs at scale.
• 10+ years of proven success managing IT portfolios and complex, multi-year technology programs within large, matrixed organizations, including oversight of budgets exceeding $20M.
• 8+ years of experience balancing strategic portfolio management with hands-on program leadership, adapting to business needs while driving successful program execution and outcomes.
• 6+ years of experience designing, implementing, and continuously improving program and portfolio governance frameworks, enhancing visibility, prioritization, risk management, and delivery performance.
• 5+ years of experience supporting Medicare programs, with a strong understanding of healthcare operations, regulatory requirements, and delivery within a complex healthcare environment.
• 5+ years of experience utilizing portfolio management and product delivery toolsets, including Rally, JIRA, roadmap planning, initiative management, and financial tracking solutions, with a commitment to continuously expanding expertise in emerging tools and practices.
• 3+ years of experience leading and developing high-performing teams, including direct management of 10+ employees, with a proven ability to coach, mentor, and foster an engaged, results-oriented culture.
• 3+ years of experience demonstrating strong communication skills and executive presence, with the ability to influence and build alignment across all levels of the organization, including senior executives and cross-functional stakeholders.
• 3+ years of experience establishing and maintaining high standards for quality, accountability, and stakeholder engagement, with a demonstrated ability to drive results through teams and cross-functional partnerships.
• 3+ years of experience successfully operating in complex and ambiguous environments, connecting priorities across multiple initiatives and driving clarity, alignment, and execution among diverse stakeholders.