Job Description

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 client requires personnel with qualifications, knowledge, skills, and capabilities as described below.

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.

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.

Required Qualifications

• 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

Citizenship

· US Citizenship

Knowledge, Skills & Abilities

• 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.

Certificates

• Any one of the Industry leading Agile practitioner certifications such as:
• Certified Scrum Master
• Certified Scrum Product Owner
• PMP-ACP or
• Scaled Agile Framework (SAFe), etc.
• MI Certification a plus, Agile program management certification preferred.

Education

• Bachelor's degree in a relevant field; advanced degree preferred

Compensation & Benefits [1][2]

• Wage Range: Negotiable
• General Benefits: Custom Software Systems, Inc. offers our employees a competitive benefits package that may include:

• Health insurance plans
• Health Savings Account (HSA)
• Dental
• Vision
• Long-term disability
• Short-term disability
• Basic term life insurance
• Supplemental term life insurance for employees, spouses, and dependents
• Simple IRA
• Parking/Commuting expense reimbursement
• Training/Education

[1] Compensation range must be coordinated with and approved by the CSS Chief Operating Officer (COO).

[2] Compensation & Benefits information is required for all Maryland Employers effective October 1, 2024.