TruStage · 4 months ago
Director IT Portfolio Management
Madison, WI
Full-time
Onsite
Director/Executive
$151K/yr - $281K/yr
12+ years expTruStage is on a mission to make a brighter financial future accessible to everyone, focusing on creating a diverse and inclusive environment. The Director of IT Portfolio Management will lead the development and governance of the IT portfolio, ensuring alignment with company goals and driving organizational transformation through collaboration and strategic planning.
Financial Services
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
Qualification
Required
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
Preferred
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
Benefits
Medical
Dental
Vision
Employee assistance program
Life insurance
Disability plans
Parental leave
Paid time off
401k
Tuition reimbursement
Company
TruStage
TruStage™ is a financially strong insurance and financial services provider, built on the philosophy of people helping people, meeting the needs of middle-market consumers and the businesses that serve them.
1001-5000 employees
H1B Sponsorship
TruStage has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (22)
2024 (15)
2023 (13)
2022 (25)
2021 (15)
2020 (15)
Funding
Current Stage
Late StageLeadership Team
Sidd Kuckreja
SVP, Chief Technology Officer
Brian J. Borakove
Senior Vice President - Deputy Chief Financial Officer
Company data provided by crunchbase