Senior Technical Program & Portfolio Manager

Salary Range: $115,000 – $135,000. The base pay offered may vary within this range based on job-related knowledge, skills, and experience.

Work Location: Preference for candidates located in Wisconsin. Employees within 45 miles of WPS Headquarters (1717 W. Broadway, Madison, WI 53713) will work onsite 2 days per week on a regular basis.

About the Role

The Senior Technical Program & Portfolio Manager drives consistent delivery across complex and cross-functional initiatives. They establish and evolve portfolio governance, ensure alignment to strategic business outcomes, and create the operating rhythm that enables transparency, accountability, and accelerated value delivery. This role flexes seamlessly across delivery disciplines, including traditional program and project management, scaled agile execution, and enterprise portfolio management, to orchestrate work across multiple teams, products, and functional groups. The role guides initiatives from conception through execution, managing scope, schedule, financials, risks, and change control.

Responsibilities

• Establish and maintain enterprise portfolio frameworks, governance structures, and operating mechanisms that ensure consistent delivery, strategic alignment, and transparent decision-making.
• Align initiatives with business objectives, ensuring measurable impact, value realization, and clear prioritization across the portfolio.
• Facilitate executive portfolio and program reviews, highlighting delivery risks, interdependencies, and resource constraints to accelerate decisions and maintain organizational alignment.
• Lead large and cross-functional programs through full lifecycle execution using predictive, agile, and hybrid approaches, ensuring scope, schedule, and budget adherence while delivering outcome-focused results.
• Identify and manage cross-team dependencies, constraints, and integration points; drive issue resolution and escalation management to prevent delays and maintain delivery flow.
• Build and maintain strong relationships across business, product, engineering, and operational teams to strengthen collaboration, trust, and shared accountability.
• Provide clear, concise, and data-driven communication of program and portfolio status, risks, milestones, and outcomes to senior leadership.
• Oversee resource planning and capacity management in partnership with product, engineering leaders, and finance to ensure optimal team utilization and investment alignment.
• Track budgets, forecasts, actuals, and burn rates; drive financial health across initiatives and identify optimization opportunities to maximize value delivery.
• Implement disciplined risk management and change control processes that preserve delivery integrity and reduce volatility across programs.
• Coordinate agile planning activities such as PI Planning and maintain cadence-based execution, improving flow metrics, predictability, and alignment across agile teams.
• Drive continuous improvement through targeted process optimization; reduce delivery cycle time and improve team throughput by refining planning, review, and execution rituals.
• Track and report operational performance metrics including deployment frequency, lead time, defect escape rate, flow efficiency, and team predictability.
• Champion transformation office best practices, delivery excellence, and agile maturity across teams and stakeholders.

Requirements

• Bachelor’s degree in Computer Science, Business, or a related field, or an equivalent combination of education and experience.
• 7 or more years of experience in technical program or project management roles.
• 3 or more years of experience at a senior or portfolio level.
• Extensive experience in execution methodologies, including Agile (Scrum, Kanban) and scaled frameworks like SAFe or LeSS.
• Extensive knowledge of structured approaches to identify, mitigate, and communicate risks and manage change control processes.
• Extensive knowledge of budgeting, forecasting, cost optimization, and financial tracking across programs.
• Demonstrated experience in stakeholder analysis, executive communication, and cross-functional alignment strategies.
• Ability to translate strategy into actionable roadmaps, orchestrating execution across multiple teams and domains.
• Ability to collaborate closely with engineering teams to understand architecture, integration, and dependencies without needing hands-on development experience.
• Demonstrated experience 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

• Experience with WPS systems, tools, and processes.
• Understanding of WPS lines of business, including Health Plan, Government Services, and Data Logistics.

Remote Work Requirements

• High-speed cable or fiber internet connection.
• Minimum of 10 Mbps downstream and at least 1 Mbps upstream (verifiable via 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 salary and a 50% match for the next 2% (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 fosters an open and empowering employee experience, recognizing the benefits of engagement as an investment in its workforce. The company values diverse perspectives to fuel agility and innovation on high-performing teams, encouraging employees to bring their authentic selves to work. This approach has earned WPS recognition from local and national organizations for its culture and workplace.