Head of Sales Illustrations

MassMutual • Springfield, MA

5d

About The Position

The Head of Illustrations owns the business strategy, roadmap, and delivery of MassMutual’s illustration capabilities across the new business and in-force experiences. This role will lead the evolution of critical advisor- and client-facing platforms, balancing near-term delivery with long-term modernization, while partnering closely with Product, Distribution, ETX, Legal, and Operations. In this role, as well as all roles within MassMutual, you will demonstrate accountability, agility, strong business acumen, and the courage to navigate complex challenges. We also highly value strong communication skills, intellectual curiosity, proactivity, resilience, and self-awareness. As part of Brand, Product and Affiliated Distribution, the Distribution Enablement organization is responsible for driving strategy and execution related to technology, reporting, readiness and change management to support MassMutual’s product, marketing and career distribution organizations. Within our organization we place a premium on our creating a diverse and inclusive team, aligning priorities with key markets and distribution channels, while nurturing partnerships with key stakeholders based on transparency and accountability.

Requirements

• Bachelor’s degree
• 10+ years leading complex product, platform, or business capabilities in a regulated environment.
• Proven experience owning and delivering multi‑year roadmaps with execution accountability.
• Demonstrated people leadership experience, including leading and developing high‑performing SME teams.
• Strong background partnering with technology teams to deliver scalable solutions.
• Demonstrated success managing senior stakeholders across multiple functions.
• Clear, confident communicator with the ability to navigate ambiguity and competing priorities.

Nice To Haves

• Experience serving as a business owner for large, multi‑year capabilities or platforms, with accountability for roadmap decisions, delivery outcomes, and stakeholder alignment.
• Demonstrated ability to lead complex initiatives without direct authority, influencing senior stakeholders across Product, Distribution, Technology, Legal, and Operations.
• Proven success leading initiatives that span process design, product evolution, and technology modernization, including system enhancements or platform transformations.
• Strong ability to synthesize business strategy, user needs, regulatory considerations, and technical constraints into clear priorities and executable plans.
• Track record of making data‑informed decisions and tradeoffs in complex, ambiguous environments.
• Comfortable challenging the status quo constructively to improve outcomes, simplify complexity, and drive continuous improvement.
• Experience balancing near‑term delivery commitments with long-term strategic objectives in a regulated or highly governed setting.

Responsibilities

• Own the end‑to‑end vision and multi‑year roadmap for illustrations, aligned to product, distribution, and enterprise priorities.
• Drive consistent delivery of illustration capabilities, translating strategy into executable plans and measurable outcomes.
• Lead and develop a team of approximately 5 Illustration Subject Matter Experts, providing clear direction, prioritization, and accountability.
• Operate as a player‑coach, leveraging team expertise while remaining closely engaged in strategy, delivery, and stakeholder conversations.
• Partner cross‑functionally with Technology, Product, Legal, Compliance, and Operations to manage dependencies, risks, and tradeoffs.
• Serve as the primary senior stakeholder point of accountability, clearly communicating priorities, progress, and delivery commitments.
• Champion advisor and client experience, ensuring illustrations are intuitive, actionable, and support effective decision‑making.
• Improve intake, prioritization, and governance processes while simplifying legacy complexity.

Benefits

• industry leading pay and benefits
• Access to mentorship opportunities
• Networking opportunities including access to Asian, Hispanic/Latinx, African American, women, LGBTQ, veteran and disability-focused Business Resource Groups
• Access to learning content on Degreed and other informational platforms

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 5,001-10,000 employees