Senior Director, Agile Transformation & Delivery

CVS Health; Boise (ID); Hybrid; USD 144,000 - 288,000; Full time

Benefits offered by this job

Bonus program

Equity awards

Comprehensive benefits

Job summary

CVS Health in Hartford, CT or Pittsburg, PA is seeking an experienced Senior Agile Delivery Leader to drive enterprise tech initiatives, establish scrum structures, coach teams, and manage large budgets.

You will partner with Engineering and Product to deliver value-based outcomes, influence strategy, and oversee 10–12 Agile Practice Leads while shaping Agile adoption across the organization. This role requires 10–15+ years of experience and a track record of transformation.

Qualifications

• 10–15+ years of professional experience, including 3–5 years in people management roles with 5+ direct reports.
• Experience managing budgets of $30M+; Strong execution and delivery skills, with planning, risk mitigation, and stakeholder engagement.
• Proven experience implementing Agile practices in complex, cross-functional environments.
• Familiarity with additional software delivery methodologies including SAFe and Waterfall.
• Demonstrated ability to influence enterprise strategy and lead large-scale transformation initiatives.
• Mastery of problem-solving, decision-making, and growth mindset principles.
• Experience with innovation management, emerging technologies, 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

People management

Budget management

Cross-functional collaboration

SAFe

Waterfall

Stakeholder engagement

Problem solving

Growth mindset

Education

Bachelor's degree

Job description

CVS Health in Hartford, CT or Pittsburg, PA is seeking an experienced Senior Agile Delivery Leader to drive enterprise tech initiatives, establish scrum structures, coach teams, and manage large budgets.

You will partner with Engineering and Product to deliver value-based outcomes, influence strategy, and oversee 10–12 Agile Practice Leads while shaping Agile adoption across the organization. This role requires 10–15+ years of experience and a track record of transformation.