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Director, Agile Program & Roadmap Governance
Role Snapshot
The Director, Agile Program & Roadmap Governance is accountable for governing, orchestrating, and maturing the Health Plan's Agile delivery framework and strategic roadmap execution. This role ensures alignment between organizational strategy, portfolio governance, and disciplined Agile execution across both technical and non‑technical Health Plan initiatives. The Director oversees portfolio management, organizational capacity and demand analysis, program 'MVP' decomposition, and prioritization governance. The individual also facilitates program-level Agile ceremonies, drives operational readiness for Program Increment execution, and ensures that delivery outcomes are transparent, predictable, compliant, and aligned with enterprise priorities. The role coaches and develops Agile and governance practitioners, strengthens organizational delivery capability and throughput, and fosters a culture of accountability, transparency, and collaboration. The Director, Agile Program & Roadmap Governance is responsible for building and sustaining governance structures that support compliant, high-quality execution in a regulated Health Plan environment.
Salary Range
160-180k
The base pay offered for this position may vary within the posted range based on your job-related knowledge, skills, and experience.
Work Location
Our first consideration will be to have this employee live in the state of Wisconsin to take advantage of Hybrid work and collaboration. Employees within 45 miles of WPS Headquarters (1717 W. Broadway in Madison, WI, 53713) will be expected to be able to be able to work Hybrid 2 days a week on a regular basis.
As a secondary consideration, we do offer remote work in the following approved states:
We are open to remote work in the following approved states:
Colorado, Florida, Georgia, Illinois, Indiana, Iowa, Michigan, Minnesota, Missouri, Nebraska, New Jersey, North Carolina, Ohio, South Carolina, Texas, Virginia, Wisconsin
How do I know this opportunity is right for me? If you:
- Lead and govern Agile execution across Health Plan initiatives by ensuring cadence, consistency, and alignment to strategic priorities.
- Facilitate and oversee key Agile ceremonies, such as program prioritization, Program Increment (PI) Planning, Scrum of Scrums, ART Sync, Inspect & Adapt, and other cross-team coordination ceremonies.
- Establish and maintain roadmap and prioritization governance processes and delivery timelines that balance technical, business, and regulatory needs.
- Strategically optimize organizational capacity and demand by identifying, balancing, and reconciling resource constraints.
- Partner with executive leadership, Product Managers, Business Owners, and delivery teams to ensure backlog readiness, prioritization, and alignment to strategic outcomes.
- Identify and resolve escalated impediments, manage cross-team dependencies, and proactively address risks that impact roadmap delivery.
- Provide visibility into delivery performance by maintaining program-level dashboards, metrics, and reporting; analyze trends to drive improvement and decision-making.
- Coach, mentor, and develop Scrum Masters, Product Owners, Analysts, and other governance and Agile delivery roles to strengthen maturity and consistency across teams.
- Drive continuous improvement initiatives, promoting best practices across Agile, execution governance, and compliance-driven delivery.
- Partner with portfolio and regulatory stakeholders to ensure adherence to governance, audit, and compliance requirements across the Health Plan.
- Champion change management and Agile transformation efforts by influencing behaviors, supporting capability development, and fostering a culture of accountability and transparency.
Minimum Qualifications
- Bachelor's degree, in Business, Computer Science, or related field, or equivalent combination of education and experience.
- Certified ScrumMaster (CSM), Certified Scrum Professional (CSP), or equivalent required, or the ability to become certified within 6 months of hire.
- 10 or more years of experience leading strategy execution, Agile governance, or program-level delivery within business and/or IT environments, to include five 5 or more years of experience leading high-performing cross-functional teams within highly regulated industry (e.g., health insurance, government programs).
- Proven leadership experience facilitating PI Planning, cross-team Agile ceremonies, and program-level execution structures within a SAFe or hybrid Agile environment.
- Strong knowledge of Agile metrics, tooling, and reporting (e.g., Jira, Azure DevOps, Rally) to support transparency, predictability, and quality delivery.
- Excellent interpersonal communication and influencing skills with the ability to drive alignment across business, technical, and executive stakeholders.
- Demonstrated ability to manage complex risks, dependencies, and decision-making across multiple teams or business units.
- Deep understanding of system development lifecycles, compliance-driven delivery requirements, and the ability to collaborate with technical and non‑technical teams.
- Ability to work in a complex, rapidly evolving environment with multiple internal and external stakeholders.
Preferred Qualifications
- Strong knowledge of the health insurance industry, its core functions, and its commercial and government insurance products/programs.
Remote Work Requirements
- High speed cable or fiber internet.
- Minimum of 10 Mbps downstream and at least 1 Mbps upstream internet connection (can be checked at
- Please review Remote Worker FAQs for additional information.
Benefits
- Remote and hybrid work options available
- Performance bonus and/or merit increase opportunities
- 401(k) with a 100% match for the first 3% of your salary and a 50% match for the next 2% of your salary (100% vested immediately)
- Competitive paid time off
- Health insurance, dental insurance, and telehealth services start DAY 1
- Professional and Leadership Development Programs
- Review additional benefits: (
Who We Are
WPS, a health solutions company, is a leading not-for-profit health insurer and federal government contractor headquartered in Madison, Wisconsin. WPS offers health insurance plans for individuals, families, seniors and group health plans for small to large businesses. We process claims and provide customer support for beneficiaries of the Medicare program and manage benefits for millions of active-duty and retired military personnel across the U.S. and abroad. WPS has been making healthcare easier for the people we serve for nearly 80 years. Proud to be military and veteran ready.
Culture Drives Our Success
WPS' culture is where the great work and innovations of our people are seen, fueled and rewarded. We accomplish this by creating an open and empowering employee experience. We recognize the benefits of employee engagement as an investment in our workforce-both current and future-to effectively seek, leverage, and include differing and unique perspectives that fuel agility and innovation on high-performing teams. This results in people bringing their authentic selves to work every day in an organization that successfully adapts to business changes and new opportunities.
We are proud of the recognition we have received from local and national organization regarding our culture and workplace: WPS Newsroom - Awards and Recognition.
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Skills:
Agile Programming Methodologies, Atlassian JIRA, Backlog Prioritization, Best Practices, Business Strategy, Cadence, Capacity Analysis, Capacity Strategy, Certified ScrumMaster, Change Management, Coaching, Communication Skills, Computer Science, Continuous Improvement, Cross-Functional, DevOps, Employee Benefits, Establish Priorities, Federal Contracts, Federal Government, Government, Government Contracts, Health Insurance, Health Plan, Healthcare, Information Technology & Information Systems, Insurance, Interpersonal Skills, Investment Management, Leadership, Machine Tool, Maintain Compliance, Mentoring, Metrics, Microsoft Windows Azure, Military, Newsroom, Nonprofit, Process Improvement, Product Programs, Reconciliation, Regulations, Regulatory Compliance, Reporting Dashboards, Risk Management, Scrum Product Owner, Scrum Project Management and Software Development, ScrumMaster, Software Development Lifecycle (SDLC), Team Lead/Manager, Team Player, Trend Analysis, Work From Home
Wisconsin Physicians Service Insurance Corp
