Custom Software Systems, Inc. (CSS) is seeking an experienced Senior Agile Program Manager to support our client’s Business and Technology Modernization (BTM) Program. The ideal candidate will provide strategic leadership and oversight of enterprise-wide Agile transformation initiatives, driving Agile maturity, standardizing best practices, and ensuring measurable business outcomes across multiple teams. This role requires a proven leader with extensive experience in Agile program management, organizational change, and team coaching who can establish effective governance, engage senior stakeholders, and continuously improve Agile practices. The successful candidate will balance strategic planning with hands-on program execution to support sustainable transformation and long-term organizational success.
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
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Citizenship
· US Citizenship
Required Qualifications
- At least ten (10) years of experience as a program manager, project manager, or project consultant for technology projects with at least 5+ years leading enterprise Agile
Transformations.
- At least five (5+) years of hands-on experience and proven track record of coaching teams.
- At least three ( 3+) years of experience of effective project/program management or system engineering experience demonstrating ability to manage complex initiatives.
- Direct experience leading agile transformations in either the federal or private space.
- Direct experience with Jira and Confluence.
Knowledge, Skills & Abilities
- Deep understanding and expertise of Scaled Agile Framework (SAFe).
- Deep expertise in multiple Agile frameworks (Scrum, Kanban, Scaled Agile Framework (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 assessments
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.
Education
- Bachelor's degree in a relevant field; advanced degree preferred
Certificates
- Industry-leading Agile practitioner certifications such as Certified Scrum Master, Certified Scrum Product Owner, PMP-ACP, or Scaled Agile Framework (SAFe), etc.
Preferred Qualifications
- Government or highly regulated industry experience 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.
Skills Required
- At least 10 years of experience as a program manager, project manager, or project consultant for technology projects
- At least 5 years leading enterprise Agile transformations
- At least 5 years of hands-on experience coaching teams
- At least 3 years of project/program management or systems engineering experience managing complex initiatives
- Direct experience leading Agile transformations in federal or private-sector environments
- Direct experience with Jira and Confluence
- Deep understanding of the Scaled Agile Framework (SAFe)
- Expertise in multiple Agile frameworks, including Scrum, Kanban, or SAFe
- Experience defining and implementing Agile maturity models and assessments
- Experience building sustainable governance models, documentation standards, engagement rhythms, and risk management processes
- Excellent stakeholder management, communication, facilitation, conflict resolution, and problem-solving skills
- Bachelor's degree in a relevant field
- Industry-leading Agile practitioner certification such as Certified Scrum Master, Certified Scrum Product Owner, PMP-ACP, or SAFe
- U.S. citizenship
- Advanced degree
- Government or highly regulated industry experience
What We Do
Welcome To Custom Software Systems, Inc. About Custom Software Systems, Inc.: Headquartered in Leesburg, Virginia, Custom Software Systems, Inc. (CSS) is a certified Woman Owned Small Business (WOSB) and certified HUBZone Business. Built on a foundation of trusted client partnerships, CSS has fostered a “stakeholder-centric”, yet disciplined approach to IT solutions development. This ensures our ability to consistently deliver on time and within budget and to meet or exceed our customers’ expectations. Core Expertise: CSS specializes in developing and implementing Custom Software Solutions and Support Services which deliver high value to our customers. Our skilled team of consultants helps our clients/partners integrate technology that fits their business needs. We provide our clients with a full array of services, including: - Project Management & Oversight (PMP certified Project Managers) - Database and Data Management (Certified DBA’s) - Data Architecture (DAMA and TDWI member) - Middleware Support (Oracle Fusion Middleware) - Application Lifecycle Management (ALM) - Oracle Fusion Middleware Support - Business Intelligence Support (WebFOCUS, Business Objects, Tableau) - Full Lifecycle Application Development (Agile, RUP, Waterfall) - Identity Management - Operations and Maintenance Core Values: CSS was founded on a set of guiding principles that include good old fashioned hard work, ethics, teamwork, and innovation. We establish relationships with our customers that are based on direct and honest communication and perseverance to get the job done which in turn fosters respect and trust. We expect our associates, at every level, to conduct themselves with integrity, honesty and strong ethics in all relationships with customers and employees.
