Lead Director, Agile Practice Management

CVS Health•Work At Home-Connecticut, CT

3d•$144,200 - $288,400•Hybrid

About The Position

The Lead Director, Agile Practice Management leads end-to-end delivery of a portfolio of strategic and regulatory technology initiatives within Aetna Commercial and Distinct Client Segments (DCS) Delivery. The role focuses on delivery execution, outcomes, financial discipline, and team-of-teams performance, balancing strategic portfolio oversight with hands-on program leadership. The leader partners with Engineering, Product, Architecture, Finance, and business leaders to set priorities, manage investments, and turn strategy into predictable, measurable results. The Lead Director develops Program Managers, Project Managers, and Scrum Masters and serves as a central connector between technology leaders and business stakeholders. They establish and mature programs, set consistent governance and reporting standards, and manage portfolio financials across capital and operating expenses, including forecasting, variance management, capacity planning, and investment trade-offs. Success is measured by delivery predictability, financial transparency, portfolio health, and a culture of accountability and continuous improvement. The role is hybrid in the Hartford, Connecticut office, which is preferred; remote candidates will also be considered.

Requirements

At least 10 years of experience in program and portfolio management, including managing large-scale, complex technology and business transformation initiatives in large, matrixed organizations.
At least 5 years of experience managing large enterprise portfolios, including annual budgets exceeding $25 million, with responsibility for strategic planning, prioritization, governance, and execution.
At least 5 years in a formal people leadership role developing project, program, and portfolio management teams, including hiring, performance management, and talent development.
Experience standing up new programs and building operating rhythms, governance, and delivery practices from the ground up.
Experience owning portfolio budgets, including forecasting, variance management, capital-versus-operating expense management, and investment trade-off decisions.
Ability to establish governance that keeps scope, schedule, budget, quality, and metrics accurate, transparent, and aligned to enterprise standards.
Expertise with project and portfolio management tools such as Jira, Rally, and Clarity, and other portfolio planning and financial management platforms.
Strong executive communication and ability to influence VP and SVP leaders, translating complex information into clear decisions and actions.
Experience operating in large, highly matrixed enterprise environments.
Current Agile, program/project management, or equivalent professional certification, such as SAFe, RTE, SPC, CSM, and/or PMP.
Bachelor’s degree in computer science, Business Management, Information Technology, or a related field; equivalent combinations of education, specialized training, certifications, and relevant professional experience will be considered.

Nice To Haves

Healthcare or insurance payer experience, ideally supporting Commercial lines of business.
Experience facilitating executive operating reviews, investment reviews, and cross-organization governance forums.
Experience coordinating internal and external staffing partners.
Expertise in product operating models.
Master’s degree.

Responsibilities

Lead end-to-end delivery of a portfolio of strategic and regulatory technology initiatives within Aetna Commercial and Distinct Client Segments Delivery.
Drive delivery execution, outcomes, financial discipline, and team-of-teams performance while balancing portfolio oversight with hands-on program leadership.
Partner with Engineering, Product, Architecture, Finance, and business leaders to set priorities, manage investments, and turn strategy into measurable results.
Develop Program Managers, Project Managers, and Scrum Masters, including hiring, performance management, and talent development.
Serve as a central connector between technology leaders and business stakeholders.
Stand up and mature programs, establishing operating rhythms, governance, delivery practices, and reporting standards.
Manage portfolio financials across capital and operating expenses, including forecasting, variance management, capacity planning, and investment trade-off decisions.
Establish governance that keeps scope, schedule, budget, quality, and metrics accurate, transparent, and aligned with enterprise standards.