TruStage Insurance Agency LLC
Director IT Portfolio Management
TruStage Insurance Agency LLC, Madison, Wisconsin, us, 53774
Director IT Portfolio Management page is loaded## Director IT Portfolio Managementlocations:
Madison, WItime type:
Full timeposted on:
Posted 2 Days Agojob requisition id:
R-011249At 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:**Job Summary:**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.**Job Responsibilities:**Portfolio Strategy, Governance & Planning* 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.Execution, Financials & Value Realization* 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.Transformation Leadership & Culture Enablement* 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.Stakeholder Engagement & Communication* 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.The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time.**Job 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.**Preferred Requirements*** 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 Managment in medium to large companiesIf you’re ready to help make a difference, apply today.
A resume is required to apply. TruStage may process applicant information using an Artificial Intelligence (AI) tool.
This tool automatically generates a screening score based on how well applicant information matches the requirements and qualifications for the position. TruStage recruiters use the screening score as a guide to further evaluate candidates; the score is one component of an application review and does not automatically determine whether a candidate moves forward.
Candidates may choose to opt out of this process.Compensation may vary based on the job level, your geographic work location, position incentive plan and exemption status. **Base Salary Range:**$151,200.00 - $281,200.00 At TruStage, we believe a sound, inclusive benefits program is of vital importance, along with a flexible workplace that allows for work-life balance, career growth and retirement assistance. In addition to your base pay, your position may be eligible for an annual incentive (bonus) plan.
Additional benefits available to eligible employees include medical, dental, vision, employee assistance program, life insurance, disability plans, parental leave, paid time off, 401k, and tuition reimbursement, just to name a few. Beyond pay and benefits, we also recognize that flexibility, including working in a place you prefer, is essential to caring for our employees.
We will continue to strive to offer flexibility and invest in technology and other tools that will make hybrid working normal rather than an exception, so that when “life happens,” you can focus on what’s most important.**Accommodation request**TruStage is a place where everyone can bring their best self and thrive. If you need application or interview process accommodations, please contact the accessibility department. #J-18808-Ljbffr
Madison, WItime type:
Full timeposted on:
Posted 2 Days Agojob requisition id:
R-011249At 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:**Job Summary:**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.**Job Responsibilities:**Portfolio Strategy, Governance & Planning* 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.Execution, Financials & Value Realization* 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.Transformation Leadership & Culture Enablement* 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.Stakeholder Engagement & Communication* 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.The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time.**Job 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.**Preferred Requirements*** 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 Managment in medium to large companiesIf you’re ready to help make a difference, apply today.
A resume is required to apply. TruStage may process applicant information using an Artificial Intelligence (AI) tool.
This tool automatically generates a screening score based on how well applicant information matches the requirements and qualifications for the position. TruStage recruiters use the screening score as a guide to further evaluate candidates; the score is one component of an application review and does not automatically determine whether a candidate moves forward.
Candidates may choose to opt out of this process.Compensation may vary based on the job level, your geographic work location, position incentive plan and exemption status. **Base Salary Range:**$151,200.00 - $281,200.00 At TruStage, we believe a sound, inclusive benefits program is of vital importance, along with a flexible workplace that allows for work-life balance, career growth and retirement assistance. In addition to your base pay, your position may be eligible for an annual incentive (bonus) plan.
Additional benefits available to eligible employees include medical, dental, vision, employee assistance program, life insurance, disability plans, parental leave, paid time off, 401k, and tuition reimbursement, just to name a few. Beyond pay and benefits, we also recognize that flexibility, including working in a place you prefer, is essential to caring for our employees.
We will continue to strive to offer flexibility and invest in technology and other tools that will make hybrid working normal rather than an exception, so that when “life happens,” you can focus on what’s most important.**Accommodation request**TruStage is a place where everyone can bring their best self and thrive. If you need application or interview process accommodations, please contact the accessibility department. #J-18808-Ljbffr