✦ Luna Orbit — Executive & General Management

Head of Sales Illustrations

at Massachusetts Mutual Life Insurance

📍 Springfield, MA Unknown 💰 $172K – $225K USD / year Posted April 15, 2026
Salary $172K – $225K USD / year
Type Not Specified
Experience executive
Exp. Years 10+ years
Education Bachelor's degree
Category Executive & General Management

The Head of Illustrations owns MassMutual’s illustration business strategy, roadmap, and delivery across new business and in-force experiences. This leader guides modernization while ensuring consistent delivery of advisor- and client-facing illustration capabilities, partnering closely with multiple functions.

  • Own the end-to-end vision and multiyear roadmap for illustrations
  • Drive consistent delivery of illustration capabilities with measurable outcomes
  • Lead and develop a team of approximately 5 Illustration Subject Matter Experts as a player-coach
  • Partner cross-functionally with Technology, Product, Legal, Compliance, and Operations to manage dependencies, risks, and tradeoffs
  • Improve intake, prioritization, and governance processes while simplifying legacy complexity

The role is primarily platform and product capability leadership, coordinating with Technology and Product to deliver scalable illustration solutions. It focuses on roadmap execution, governance, and modernization of legacy illustration complexity rather than hands-on software development.

The ideal candidate is a senior leader with 10+ years leading complex product, platform, or business capabilities in a regulated environment, owning multiyear roadmaps with clear execution accountability. They have strong people leadership experience managing and developing high-performing SME teams, and proven cross-functional partnership with technology and business stakeholders to deliver scalable, modern advisor- and client-facing experiences.

Bachelor's degree10+ years leading complex productplatformor business capabilities in a regulated environmentowning and delivering multiyear roadmaps with execution accountabilitypeople leadership experience including leading and developing high-performing SME teamspartnering with technology teams to deliver scalable solutionsmanaging senior stakeholders across multiple functionsclearconfident communicator able to navigate ambiguity and competing priorities
experience serving as a business owner for largemulti-channeltechnology-enabled experiencesexperience in advisor experience and client experience improvementexperience with illustration governance and modernization
business strategyroadmapmultiyear roadmapend-to-end visionexecution accountabilitypeople leadershipSME teamssubject matter expertscross-functional partnershipstakeholder managementregulated environmentadvisor experienceclient experiencegovernance processesintake prioritizationlegacy modernizationrisk managementdependency managementtradeoff managementchange managementplayer-coach
business strategyroadmap ownershipmultiyear roadmap deliveryproduct platform deliveryillustration capabilitiesadvisor-facing platformsclient-facing platformsend-to-end visionintake prioritizationgovernance processeslegacy modernizationstakeholder managementrisk managementdependency managementtradeoff managementcross-functional partnershipchange managementteam leadershipplayer-coach operating modelmeasurable outcomes deliverycommunication of priorities and progress
accountabilityagilitystrong business acumencourage to navigate complex challengesstrong communication skillsintellectual curiosityproactivityresilienceself-awarenessnavigate ambiguityconfident communicatorprioritizationresilience under competing prioritiesclear direction settingtransparencycollaboration
Industry Insurance
Job Function Lead and deliver MassMutual’s illustration strategy, roadmap, and execution across advisor- and client-facing platforms.
Role Subtype General Manager
Head of Sales IllustrationsHead of Illustrationsillustrationsbusiness strategyroadmapmultiyear roadmapend-to-end visionexecution accountabilityplayercoachplayer-coachpeople leadershipSME teamssubject matter expertscross-functionalTechnologyProductDistributionLegalComplianceOperationsstakeholder managementregulated environmentadvisor experienceclient experiencegovernance processesintake prioritization

Bachelor's degree required, 10+ years leading complex product, platform, or business capabilities in a regulated environment, Must have multiyear roadmap ownership with execution accountability, Must have people leadership experience leading and developing high-performing SME teams

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