Senior Technical Program & Portfolio Manager

Wis Phys Svc Ins Corp • Full-time • Madison, Wisconsin, United States • $120,000 - $140,000 / year • 4w ago

Role Snapshot

Our Senior Technical Program & Portfolio Manager is accountable to drive consistent execution and delivery across complex, cross-functional programs by establishing portfolio governance frameworks and aligning initiatives with strategic business objectives in a scaled agile framework (SAFe®). This Manager leads programs or projects from initiation through completion, ensuring scope, schedule, and budget adherence while proactively managing risks, resolving issues, and maintaining momentum. They will facilitate executive-level reviews to support accountability and accelerate decision-making. Oversees resource planning and financial management to optimize investments and ensure program efficiency. Will foster strong stakeholder relationships and communicate program status and outcomes with clarity to ensure alignment, strategic cohesion, and sustained delivery performance. Leverage the SAFe® framework to participate in Agile Release Trains and facilitate effective PI Planning, ensuring synchronized execution and alignment across teams and programs.

Salary Range
$120,000 ~ $140,000
The base pay offered for this position may vary within the posted range based on your job-related knowledge, skills, experience and may fall outside the posted range.

Work Location
Hybrid – This employee will be expected to be able to work Hybrid 3 days a week on a regular basis, out of our WPS Headquarters (1717 W. Broadway in Madison, WI).

How do I know this opportunity is right for me? If you:

Can define and maintain portfolio frameworks and governance structures that enable consistent execution and delivery across programs.
Would enjoy aligning initiatives with strategic business objectives to ensure measurable impact and value realization.
Like to facilitate executive-level portfolio reviews and reporting to drive accountability, surface delivery risks, and accelerate decision-making.
Have led complex, cross-functional programs from initiation through execution, driving delivery of high-impact outcomes. Ensure adherence to scope, schedule, and budget across all phases of the program lifecycle.
Can resolve escalated issues and actively manage interdependencies to maintain momentum and prevent delays.
Would enjoy building strong relationships with business and technical stakeholders to foster trust and collaboration while facilitating decision-making and alignment across teams to ensure consistent progress and strategic cohesion.
Have communicated program status, risks, and outcomes to leadership with clarity and precision.
Like to oversee resource planning and capacity management across programs to ensure optimal allocation and utilization by working with application or product owners.
Can track budgets, forecasts, and actuals to maintain financial health and accountability by identifying cost-saving opportunities and optimizing investments to maximize program value and efficiency.
Enjoy identifying, assessing, and mitigating risks across the program portfolio to ensure delivery stability and resilience.
Have managed change control processes with structured impact analysis to maintain alignment and minimize disruption to scope, schedule, and resources.
Want to implement targeted process improvements to reduce delivery cycle time and accelerate execution while increasing sprint predictability and velocity by refining planning and delivery rituals.
Can track and report key operational KPIs, including defect escape rate, deployment frequency, and lead time for changes.
Want to champion delivery best practices and agile maturity to drive continuous improvement across programs.

Minimum Qualifications

Bachelor's degree in Computer Science, Business, or related field or equivalent combination of education and experience.
7 or more years of experience in technical program or project management roles.
3 or more years working at a senior or portfolio level.
Extensive experience in Agile methodologies (Scrum, Kanban) and scaled frameworks like SAFe® or LeSS.
Extensive knowledge and understanding of structured approaches to identify, mitigate, and communicate risks and manage change control processes.
Strong understanding and knowledge of Technical Program & Portfolio Management including:
- Budgeting, forecasting, cost optimization, and financial tracking across programs.
- Stakeholder analysis, executive communication, and cross-functional alignment strategies.
- Aligning technical programs with business goals and translating strategy into actionable roadmaps.
- Engage with engineering teams on architecture, integration, and dependencies without being hands-on.
- Using KPIs, dashboards, and analytics to guide execution and report outcomes.
- Exceptional organizational, analytical, and problem-solving skills.
- Excellent written and verbal communication skills, with the ability to influence at all levels of the organization.

Preferred Qualifications

3 or more years working in SAFe® environments.
The ability and experience to influence without direct authority.
Strong experience using MS tools, Teams, MS Excel.
Experience with Agile tools such as ADO, Jira.
Certifications: PMP, and at least one SAFe® certification.

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 https://speedtest.net)
Please review Remote Worker FAQs for additional information

Benefits

Hybrid work
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: (https://www.wpshealthsolutions.com/careers/fulltime_benefits.shtml)

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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This position may from time to time provide support to federal health care programs and other governmental or regulated industries. In accordance with law and/or contractual requirements, individuals in this role are or may be subject to all applicable federal regulations, agency contract requirements, and WPS internal policies, including but not limited to standards for data security, privacy, confidentiality, and program integrity. WPS and its personnel are subject to mandatory enhanced screening and background investigation prior to being granted access to information systems and/or sensitive data in order to safeguard regulated information and government resources that provide critical services.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.