Agile Program Manager

Custom Software Systems Inc.•Washington, DC

5d•Onsite

About The Position

Custom Software Systems, Inc. (CSS) is seeking a skilled Agile Program Manager to assist with the F&M program on an as-needed basis. The Agile Program Manager is responsible for leading the strategic direction and operational execution of our Agile transformation program. This senior role will be responsible for driving team maturity, ensuring Agile resource effectiveness, maintaining playbook consistency, and achieving measurable business value across multiple teams, with planned expansion. The person will work closely with the manager of the Transformation Office, program sponsors, and business stakeholders to build a sustainable, data-driven Agile program that adapts to our organizational culture while maintaining rigor and consistency. This is a strategic role requiring someone who can both operate and innovate—executing day-to-day program management while shaping the future direction of our Agile practices. The candidate must have direct experience leading agile transformations in either the federal or private space. This is an on-site position.

Requirements

10+ years of professional experience with at least 5+ years leading enterprise Agile transformations
At least 10 years of experience as a program manager, project manager, or project consultant for technology projects.
At least 5+ years of hands-on experience and proven track record of coaching teams
At least 3+ years of experience of effective project/program management or systems engineering experience demonstrating ability to manage complex initiatives
Technology implementation experience
US Citizenship

Nice To Haves

Deep expertise in multiple Agile frameworks (Scrum, Kanban, SAFe, or similar) with ability to adapt practices to organizational culture rather than rigid framework adherence
Demonstrated ability to define and implement Agile maturity models and assessment frameworks
Strategic thinker with track record of evolving Agile practices, recommending improvements, and driving organizational change
Excellent stakeholder management skills with 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
Government or highly regulated industry experience preferred.
MI Certification a plus, Agile program management certification 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/throughput
Ensure Agile resource effectiveness by establishing performance standards for Coaches and Scrum Masters, monitoring coaching quality, resolving team/coach conflicts, and providing evidence-based recommendations on resource performance
Ensure consistent application of the Agile playbook across all teams, coaches, and Scrum Masters to maintain standardization, alignment, and continuity in Agile practices.
Drive business value realization by ensuring Agile teams deliver work that meets expected business outcomes through coaching oversight, metrics analysis, and alignment between team outputs and program objectives
Build sustainable program governance through documented processes, stakeholder engagement rhythms, risk management protocols, resource management systems, and strategic recommendations that enable long-term program success
Shape program strategy by continuously assessing program effectiveness, piloting innovative practices, recommending adaptations to our Agile approach, and ensuring the program evolves with organizational maturity.
Responsible for the overall management of the specific task order(s) and ensuring that the technical solutions and schedules in the task order are implemented in a timely manner.
Performs enterprise-wide horizontal integration planning and interfaces to other functional systems.
Responsible for formulating and enforcing work standards, assigning contractor schedules, reviewing work discrepancies, supervising contractor personnel, and communicating policies, purposes, and goals of the organization to subordinates.
Responsible for overall contract performance.