Strategic Planning & Delivery, Workstream Lead

The Opportunity

The Workstream Lead (“WSL”) is a critical leadership role within Strategic Planning & Delivery (“SP&D”), responsible for guiding strategic efforts across multiple initiatives within a designated workstream. Reporting directly to the Head of SP&D, this role offers consistent engagement with senior leaders and visibility into enterprise-wide strategy. As a WSL, you will champion transformation by connecting strategic priorities to execution, ensuring initiatives deliver meaningful impact beyond process compliance. You will cultivate trust and credibility across the organization, positioning SP&D as a strategic ally through transparent communication and collaborative engagement. You are accountable for the day-to-day leadership of your workstream and for delivering against established goals through disciplined governance, coaching, and cross-functional collaboration. A successful WSL inspires action and drives change. You think strategically across the enterprise, engage and influence senior leaders, and coach initiative owners through planning and execution. You bring strong financial acumen and analytical skills to assess value, pressure-test assumptions, and guide decision-making. You are comfortable navigating ambiguity, challenging assumptions, and presenting insights with clarity and confidence. Your ability to foster alignment, build partnerships, and lead with transparency positions SP&D as a trusted and impactful force across the organization.

The Team

The SP&D Office was established in 2019 to oversee the planning, governance, and execution of strategic initiatives that drive enterprise transformation and growth. It ensures strategic alignment, prioritization, and value realization across MassMutual’s portfolio, partnering closely with the Executive Leadership Team (“ELT”), which acts as its Steering Committee. SP&D is known for its disciplined approach to financial oversight, cross-functional collaboration, and transparent governance processes that span all phases of project maturity—from intake and discovery to implementation and tracking. The team includes roles such as Workstream Leads, Insight Leads, Finance Leads and Program Managers, each accountable for driving execution, managing budgets, and enabling decision-making through data and reporting. The team plays a critical role in fostering enterprise-wide trust and collaboration, positioning SP&D as a strategic ally to business leaders and initiative owners. SP&D has successfully governed over 300 initiatives, contributing significantly to sustainable earnings and helping MassMutual stay aligned with its strategic vision of financial well-being for all Americans.

The Impact

The Workstream Lead (“WSL”) plays a pivotal role in driving strategic execution across their assigned portfolio. They are responsible for aligning initiatives to enterprise goals, managing risks, and ensuring that projects deliver or exceed their projected ROI. WSLs act as strategic advisors to Initiative Owners, coaching them through planning, governance, and execution while pressure-testing assumptions and surfacing barriers to success. Their impact is amplified through cross-functional collaboration, data-driven decision-making, and consistent engagement with ELT, Sponsors, and project teams to maintain portfolio health and strategic alignment.

Key Responsibilities

Ideation – Apply human-centered design principles to help teams uncover and address core business challenges. Focus on solving root issues rather than symptoms, while keeping people at the center of the solution Coaching - Guide initiative owners and cross-functional teams during ideation sessions to identify value, build strong cost / benefit analysis, develop execution plans, and to coordinate across functional areas to ensure strategic alignment. The WSL is also responsible for coaching initiative owners to present plans, results, opportunities and business risks to the Workstream Sponsor, Head of SP&D and other senior leaders.

Inspirational Leader – Inspire colleagues and leaders throughout the business to embrace a culture of continuous improvement and transformation. Drive mindset shifts and behavioral change that support enterprise goals.

Analytics / Reporting –Proactively review and analyze financial health of workstream; report on the progress of workstream and initiatives, track performance of initiatives and identify key risks to value and execution. Partner with SP&D Finance on matters relating to valuing initiatives and managing workstream budget.

Value Creation - Work across a matrixed organization to bridge ideas and opportunities to increase profitability for the business. Facilitate ideation sessions , consisting of dozens of employees, which identify opportunities to enhance business profitability.

Oversight – Review milestones and key performance indicators to identify risk of execution and collaborate with Sponsors to mitigate risk and avoid value slippage. Ensure the integrity of data and adherence to SP&D policies.

Collaboration - Work closely with other workstream leads and business leaders to resolve issues share insights, and ensure alignment to workstream and enterprise goals.

The Minimum Qualifications

Bachelor’s Degree

10+ years leading teams or delivering solutions for complex, cross-functional matters Able to present work employing different storytelling techniques, promoting the process and educating team members and stakeholders. Presents recommendations backed by analysis and solution options

Self-driven and adaptable, with the ability to operate hands-on in a fast-paced, dynamic environment while effectively influencing stakeholders across the organization to drive execution. Track record of delivering executive-level presentations that clearly communicate business performance, strategic insights, and recommendations to senior leadership. Extensive experience in analyzing results and drawing insightful conclusions

Microsoft office (with exceptional Excel and PowerPoint Skills)

Demonstrated ability to analyze complex data sets and apply financial insights to identify profitability drivers, inform strategic decisions, and optimize business outcomes. Ability to work with senior leaders, offering constructive challenge and insight to influence outcomes and accelerate execution. Proven ability to lead through a matrix organization, providing direct feedback to partners at varying levels and from all areas of the broader organization

The Ideal Qualifications

Strategic Thinking & Business Insight : A WSL is expected to think strategically across the enterprise, identify opportunities to add value, and align initiatives with MassMutual’s long-term goals.

Leadership & Influence : The ideal candidate brings the ability to inspire action, coach Initiative Owners, and influence senior leaders and cross-functional teams. WSLs lead multiple workstreams and are accountable for delivering on established goals.

Execution & Governance Expertise : WSLs are responsible for managing the workstream portfolio, ensuring adherence to SP&D’s governance standards, and driving initiatives from ideation through execution. They must be comfortable with financial oversight, risk management, and reporting on portfolio health.

Analytical & Financial Acumen : Strong analytical skills and financial literacy are essential. WSLs will help assess initiative ROI, manage budgets, and ensure benefits are realized in the company’s general ledger.

Communication & Collaboration : Effective communication and collaboration across matrixed teams are critical. WSLs prepare sponsors for meetings, facilitate huddles, and ensure data integrity in systems like Wave.

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MassMutual is an equal employment opportunity employer. We welcome all persons to apply.

If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.