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.

Sign up for Job Alerts

FOLLOW US!

Instagram

LinkedIn

Facebook

WPS Health Blog


Remote

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



Back to blog

Other Jobs To Apply

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...