Senior Agile Program Manager

Custom Software Systems Inc.•Washington, DC

About The Position

Custom Software Systems, Inc. (CSS) is seeking an experienced Senior Agile Program Manager to support a client’s Business and Technology Modernization (BTM) Program. This role provides strategic leadership and oversight of enterprise-wide Agile transformation initiatives, driving Agile maturity, standardizing best practices, and ensuring measurable business outcomes across multiple teams. The role balances strategic planning with hands-on program execution, organizational change, and team coaching to support sustainable transformation and long-term organizational success. US citizenship is required.

Requirements

At least 10 years of experience as a program manager, project manager, or project consultant for technology projects, including at least 5 years leading enterprise Agile transformations.
At least 5 years of hands-on experience coaching teams, with a proven track record.
At least 3 years of effective project/program management or systems engineering experience demonstrating the ability to manage complex initiatives.
Direct experience leading Agile transformations in the federal or private sector.
Direct experience with Jira and Confluence.
Deep understanding and expertise in the Scaled Agile Framework (SAFe).
Expertise in multiple Agile frameworks, such as Scrum, Kanban, or SAFe, and ability to adapt practices to organizational culture rather than adhere rigidly to a framework.
Ability to define and implement Agile maturity models and assessment frameworks.
Strategic thinking and a track record of evolving Agile practices, recommending improvements, and driving organizational change.
Strong stakeholder management skills, including ability to engage and influence senior leadership, sponsors, and business stakeholders.
Experience building sustainable governance models, including documentation standards, engagement rhythms, and risk management.
Strong conflict resolution and problem-solving skills for addressing team dynamics and resource challenges.
Excellent communication skills, including status reporting, presentations, and facilitation.
US citizenship required.
Bachelor’s degree in a relevant field.
Industry-leading Agile practitioner certification, such as Certified Scrum Master, Certified Scrum Product Owner, PMP-ACP, or a SAFe certification.

Nice To Haves

Advanced degree preferred.
Government or highly regulated industry experience preferred.

Responsibilities

Establish and maintain transparency with program stakeholders through meaningful status reporting, proactive communication of changes, data-driven insights on team progress, and regular engagement with sponsors and business stakeholders.
Drive team maturity progression by implementing and maintaining assessment frameworks, ensuring Agile Coaches create and execute coaching plans, measuring advancement, and recommending maturity models and metrics beyond velocity and throughput.
Ensure Agile resource effectiveness by establishing performance standards for Coaches and Scrum Masters, monitoring coaching quality, resolving team and coach conflicts, and providing evidence-based recommendations on resource performance.
Ensure consistent application of the Agile playbook across teams, coaches, and Scrum Masters to maintain standardization, alignment, and continuity in Agile practices.
Drive business value realization by overseeing coaching, analyzing metrics, and aligning team outputs with program objectives so Agile teams deliver work that meets expected business outcomes.
Build sustainable program governance through documented processes, stakeholder engagement rhythms, risk management protocols, resource management systems, and strategic recommendations.
Shape program strategy by assessing program effectiveness, piloting innovative practices, recommending adaptations to the Agile approach, and ensuring the program evolves with organizational maturity.