Director, Business Office Planning (Hybrid)

TruStage; Madison (WI); Hybrid; USD 129,000 - 239,000; Full time

Job summary

TruStage in Madison, WI seeks a Director, Business Office Planning to lead portfolio planning, governance, and delivery across the Business Office. You’ll align priorities with segment leaders and translate strategy into a practical 12–18 month roadmap that informs funding, resource decisions and execution plans.

You’ll develop a high-performing team, establish reporting standards, monitor portfolio health and risks, and partner with strategy, finance and technology to drive data-driven

Qualifications

• Bachelor's degree in Business Administration, Management, or a related field.
• 12+ years in strategic planning or portfolio management.
• Experience leading cross-functional teams and governance frameworks.
• Strong ability to connect strategy with executable roadmaps.
• Proficiency with portfolio data, reporting, and OKRs.

Responsibilities

• Lead Business Office planning forums to align priorities and resources.
• Establish governance frameworks for portfolio investments.
• Collaborate with strategy, finance, and technology to align decisions.
• Ensure governance standards across portfolio initiatives.
• Provide insights to leadership for proactive decisions.
• Develop portfolio performance reporting and roadmaps.
• Mentor and develop portfolio management team.

Skills

Leadership

Portfolio Planning

Governance

Strategic Alignment

Stakeholder Collaboration

Education

Bachelor’s degree in Business Administration/Management

Tools

OKRs

Job description

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 and financial services 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

Job Purpose:

The Director, Business Office Planning is a leadership role within the Business Office, accountable for driving effective operation of Business Office planning, prioritization and governance. This position ensures strategic alignment, prioritization, and resource optimization, and delivery transparency across the business office to support achievement of business segment financial targets and objectives.

The Director leads a team responsible for portfolio planning, roadmap management, governance, and investment decision support. The role oversees the development and maintenance of the business office 12–18-month delivery roadmap, facilitates portfolio prioritization and planning processes, and provides data-driven recommendations regarding funding decisions, resource tradeoffs, initiative readiness, and portfolio performance. The Director collaborates closely with segment leaders, strategy, finance, and technology leaders, to ensure successful execution of business priorities.

Job Responsibilities:

Business Office Planning & Governance Leadership:

• Facilitate business office planning forums to align on priorities, dependencies, and resource allocation with segment leadership.

• Establish, maintain and continuously improve business ofifce planning governance frameworks to ensure strategic alignment, prioritization, and effective execution of portfolio investments.

• Collaborate with key stakeholders (e.g., strategy, finance, technology) to align portfolio decisions with strategic objectives and outcomes.

• Partner with Portfolio Lead to ensure governance standards are consistently applied across portfolio initiatives, including initiative readiness, quality assurance, dependency management, and execution monitoring.

• Drive transparency and accountability for portfolio decisions, delivery commitments, and execution outcomes.

Portfolio Planning & Prioritization:

• Business Office Portfolio Roadmap: Oversee the development and maintenance of the 12-18 month delivery roadmap, providing a clear view of priorities, milestones, dependencies, sequencing, and resource needs.

• Lead annual, quarterly, and ongoing portfolio planning processes that translate segment strategy into executable priorities; represent the Business Office at enterprise technology intake and sequencing meetings to ingest this work.

• Provide recommendations on portfolio investments, funding decisions, and resource allocation to optimize business outcomes.

• Monitor portfolio demand and capacity to ensure alignment between planned initiatives and available resources.

• Drive execution planning discipline across portfolio initiatives to improve predictability and delivery success

Portfolio Performance and Delivery Oversight:

• Monitor portfolio health, delivery progress, risks and execution challenges across the business office portfolio.

• Facilitate the escalation and resolution of portfolio issues and cross functional dependencies.

• Provide insights and recommendations to the business office leadership team, enabling proactive decision-making.

Performance Monitoring and Reporting:

• Develop and maintain portfolio performance reporting, roadmap dashboards, funding analytics, and governance reporting to support Business Office decision-making.

• Deliver accurate, timely, and actionable insights on portfolio health, resource utilization, roadmap progress, and investment performance.

• Establish reporting standards that enable consistent portfolio visibility and informed prioritization decisions.

Team Leadership and Accountability:

• Lead, mentor, and develop Business Office portfolio management leads, Portfolio Planning Consultants, andPortfolio and Process Analysts.

• Provide strategic leadership for portfolio planning, roadmap management, governance, prioritization and business performance reporting.

• Live into and role model TruStage leadership expectations.

• Foster a culture of collaboration, accountability, data-driven decision making and execution excellence.

• Conduct regular performance reviews and provide coaching and feedback to team.

• Identify training needs and opportunities for team members, providing support and encouragement for continued growth and professional development.

Key Outputs:

• Business Office Delivery Roadmap: A 12–18-month view of initiatives, milestones, dependencies, resource requirements, and sequencing.

• Portfolio Prioritization and Investment Recommendations: Data-driven analyses supporting funding, resource, and prioritization decisions.

• Portfolio Health and Performance Reporting: Visibility into portfolio progress, capacity utilization, risks, and execution effectiveness.

• Business Office Planning & Governance Frameworks: Standards for initiative readiness, quality assurance, prioritization, and execution.

• Strategic Planning Insights and Tradeoff Analyses: Recommendations supporting achievement of segment objectives and optimal resource allocation.

The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time.

Job Requirements:

• Education: Bachelor’s degree in Business Administration, Management, or a related field, or equivalent combination of education and/or related professional work experience

• 12+ years in strategic planning, business office leadership, portfolio management, execution planning, or a related discipline.

• Demonstrated experience leading cross-functional teams and integrating governance frameworks across complex organizations.

• Strong background in business planning, portfolio prioritization, resource optimization, delivery roadmapping, and investment decision support.

• Experience facilitating prioritization and tradeoff discussions with senior business leaders.

• Demonstrated ability to connect strategic objectives with executable roadmaps and delivery plans.

• Experience using portfolio data and performance insights to influence funding, capacity, and portfolio decisions.

• Ability to synthesize complex data into actionable insights for strategic decision‑making.

• Proficiency in portfolio management tools, reporting platforms, and planning methodologies (e.g., OKRs, capacity planning, dependency management).

• Exceptional leadership, communication, and facilitation skills to engage with senior executives and cross-functional teams.

Compensation may vary based on the job level, your geographic work location, position incentive plan and exemption status.

Base Salary Range:

$128,500.00 - $239,000.00

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.