Strategic Agile Program & Roadmap Director

WPS Health Solutions; Monona (WI); Hybrid; USD 160,000 - 180,000; Full time

Benefits offered by this job

Remote and hybrid work options

Performance bonus

401(k) with match

Generous PTO

Health insurance starting day 1

Professional development programs

Know Your Rights information

Job summary

WPS Health Solutions is seeking a Director to govern Agile delivery and manage the Health Plan's strategic roadmap. You will align strategy, portfolio governance, and disciplined Agile execution across initiatives while coaching governance practitioners and improving delivery throughput.

The role requires extensive experience in Agile governance, SAFe or hybrid environments, and the ability to balance technical, business, and regulatory needs.

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 nontechnical teams.
• Ability to work in a complex, rapidly evolving environment with multiple internal and externalstakeholders.

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.

Skills

Leading strategy execution

Agile governance

SAFe / Scrum

Jira/Azure DevOps/Rally

Communication & influencing

Education

Bachelor's degree in Business/CS or related

CSM certification

Tools

Jira

Azure DevOps

Rally

Job description

WPS Health Solutions is seeking a Director to govern Agile delivery and manage the Health Plan's strategic roadmap. You will align strategy, portfolio governance, and disciplined Agile execution across initiatives while coaching governance practitioners and improving delivery throughput.

The role requires extensive experience in Agile governance, SAFe or hybrid environments, and the ability to balance technical, business, and regulatory needs.