Director IT Portfolio Management

TruStage • Madison, WI

104d • $151,200 - $281,200

About The Position

At TruStage, we’re on a mission to make a brighter financial future accessible to everyone. We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance, investment and technology solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition. The TruStage technology organization plays a critical role in enabling scalable, customer-focused solutions. This position is responsible for the development and leadership of the TruStage IT portfolio, ensuring alignment with company goals, robust portfolio governance, roadmap development, and value management through strong financial governance. The incumbent drives organizational transformation, enabling a culture that thrives on ambiguity and change. The role is responsible for leading high-performing teams and driving collaboration across business units and shared services to achieve positive outcomes.

Requirements

• Bachelor’s degree in business, computer science, engineering, or related field, or equivalent combination of education and/or related professional work experience; master’s degree preferred.
• 12+ years of progressive leadership experience within technology organizations, with deep experience in portfolio management, strategic planning, or enterprise PMO roles.
• Proven track record of managing large-scale, complex technology portfolios and transformation programs.
• Expertise in full lifecycle project/portfolio management, SDLC, and Agile delivery (e.g., Scrum, Kanban, SAFe).
• Demonstrated ability to lead high-performing teams and drive operational maturity in ambiguous and evolving environments.
• Strong command of financial planning, budgeting, funding models, and technology value realization.
• Proficiency with tools such as Jira, Jira Align, ServiceNow, Apptio, Power BI, and Confluence.
• Exceptional verbal and written communication skills; adept at influencing and engaging at the executive level.

Nice To Haves

• Relevant certifications (e.g., PMP, SAFe LPM, PMI-ACP, MoP).
• In-depth experience in insurance, finance, or healthcare industry.
• Prior experience leading transformation or building of IT Portfolio Management in medium to large companies.

Responsibilities

• Develop and lead the enterprise IT portfolio strategy aligned to TruStage's strategic goals, balancing Run, Grow, and Transform investments.
• Institutionalize portfolio governance processes including intake, prioritization, funding allocation, and quarterly planning in partnership with business, finance, and architecture.
• Define and apply data-driven frameworks to guide investment tradeoffs and enable transparent decision making across the portfolio.
• Advance enterprise roadmap and strategic alignment through structured planning cadences, ensuring OKR integration and enterprise-wide collaboration.
• Oversee delivery health, risk management, and benefits realization across initiatives, embedding KPI tracking and performance insights into executive dashboards.
• Drive value management through proactive financial governance, including monthly/quarterly forecasting, actuals reconciliation, and long-range planning.
• Optimize resource capacity and utilization across delivery teams; maintain real-time visibility into skills demand, team velocity, and delivery constraints.
• Champion the use of modern tools (e.g., Jira, Confluence, Power BI, ServiceNow) to enable a single source of truth and operational transparency.
• Lead organizational shift from project delivery to business outcome ownership; foster a high performing, inclusive culture that thrives in ambiguity and change.
• Establish continuous learning practices through feedback loops, retrospectives, and knowledge-sharing forums that support agile and lean maturity.
• Act as a thought leader in Lean Portfolio Management, change enablement, and value stream optimization, coach initiative owners on execution excellence.
• Model collaborative leadership; empower teams with clarity, remove barriers, and drive alignment across stakeholder groups.
• Facilitate cross-functional collaboration across business and shared services to surface demand, resolve delivery friction, and accelerate outcomes.
• Own the communication rhythm across portfolio forums including MORs, investment reviews, and steering committees.
• Build trust and influence by aligning partners around shared goals, financial expectations, and operational success criteria.

Benefits

• Medical, dental, vision insurance.
• Employee assistance program.
• Life insurance.
• Disability plans.
• Parental leave.
• Paid time off.
• 401k.
• Tuition reimbursement.
• Annual incentive (bonus) plan.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Bachelor's degree