Director, Agile Program & Roadmap Governance

Accountable for governing, orchestrating, and maturing the Health Plan’s Agile delivery framework and strategic roadmap execution. Ensures alignment between organizational strategy, portfolio governance, and disciplined Agile execution across both technical and non-technical Health Plan initiatives. Oversees portfolio management, organizational capacity and demand analysis, program ‘MVP’ decomposition, and prioritization governance. Facilitates program-level Agile ceremonies, drives operational readiness for Program Increment execution, and ensures delivery outcomes are transparent, predictable, compliant, and aligned with enterprise priorities. Coaches and develops Agile and governance practitioners, strengthens organizational delivery capability and throughput, and fosters a culture of accountability, transparency, and collaboration. Builds and sustains governance structures that support compliant, high-quality execution in a regulated Health Plan environment.

Responsibilities

• 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.

Requirements

• 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, including five or more years of experience leading high-performing cross-functional teams within a 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.

Pay

Salary Range: $160,000 - $180,000. The base pay offered for this position may vary within the posted range based on your job-related knowledge, skills, and experience.

Work Location

First consideration will be given to candidates living in Wisconsin for hybrid work and collaboration. Employees within 45 miles of WPS Headquarters (1717 W. Broadway, Madison, WI, 53713) will be expected to work hybrid 2 days a week on a regular basis. Remote work is also available 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.

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 speedtest.net).

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 starting on day 1.
• Professional and Leadership Development Programs.

About the Company

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. The company processes claims and provides customer support for Medicare beneficiaries and manages benefits for millions of active-duty and retired military personnel across the U.S. and abroad. WPS has been making healthcare easier for nearly 80 years and is proud to be military and veteran ready.

Culture

WPS’ culture fosters an open and empowering employee experience, recognizing the benefits of engagement as an investment in the workforce. The company values differing and unique perspectives to fuel agility and innovation on high-performing teams, encouraging employees to bring their authentic selves to work. This approach helps WPS adapt to business changes and new opportunities. The organization has received recognition from local and national entities for its culture and workplace.