Senior Director of Agile Transformation & Delivery

CVS Health; Dover (DE); On-site; USD 144,000 - 288,000; Full time

Job summary

CVS Health is seeking an accomplished leader to drive enterprise delivery of complex technology initiatives. You will shape Agile practices, coach teams, and guide cross-functional Product Owners, Engineers, and Executives toward value-driven outcomes.

With 10–12 Agile Practice Leads and a $35M–$50M budget, you will influence strategy, build high-performing teams, and champion change management to sustain Agile transformation across the organization.

Qualifications

• 10–15+ years of professional experience with 3–5 years in people management (5+ direct reports).
• Experience managing budgets of $30M+ and strong execution, risk mitigation, stakeholder engagement.
• Proven track record implementing Agile practices in complex, cross-functional environments.
• Familiar with SAFe and Waterfall methodologies.
• Ability to influence enterprise strategy and lead large-scale transformations.
• Strong problem-solving, decision-making, and growth mindset.
• Experience with innovation management and digital transformation.

Responsibilities

• Lead enterprise delivery of multiple, highly complex technology initiatives aligned to government lines of business.
• Partner with Engineering and Product teams to execute delivery of value-based outcomes based on the product roadmap.
• Contribute to business objectives and strategies to increase productivity and enable faster time-to-market for products and features in order to stay competitive in a rapidly evolving market.
• Manage annual portfolio budgets of $35M – $50M and a team of 10-12 scrum masters and/or program managers.
• Identifies initiative delivery risks and issues, and manages through to mitigation and resolution.
• Drive Agile adoption across the organization including engage with executive stakeholders to communicate Agile value, influence prioritization, and support strategic decision-making.
• Drive business outcomes by increasing productivity, accelerating time-to-market, and enhancing cross-functional collaboration.
• Develop and execute change management plans to support Agile transformation and sustainability.
• Define and manage metrics and reporting standards to provide visibility into Agile performance and inform continuous improvement.
• Lead talent development initiatives, including coaching, mentoring, and succession planning.
• Contributes to top-level decision making on delivery governance and compliance protocols to ensure adherence with organizational policies, standards, and regulations.

Skills

Agile delivery

Budget management

Stakeholder engagement

Cross-functional leadership

SAFe experience

Waterfall experience

Problem solving

Education

Bachelor's degree

Tools

SAFe

Waterfall

Job description

CVS Health is seeking an accomplished leader to drive enterprise delivery of complex technology initiatives. You will shape Agile practices, coach teams, and guide cross-functional Product Owners, Engineers, and Executives toward value-driven outcomes.

With 10–12 Agile Practice Leads and a $35M–$50M budget, you will influence strategy, build high-performing teams, and champion change management to sustain Agile transformation across the organization.