Disability Underwriting Director

MassMutual • Milwaukee, WI

2d • Hybrid

About The Position

The Disability Underwriting Director leads a team of underwriting consultants supporting MassMutual’s Financial Advisors distribution channel, including career agents, individual brokers, and the consumers they serve. The role provides coaching, answers questions, and guides the team on workflow, procedures, resources, and underwriting. The director maintains awareness of department service-level requirements, supports the team in meeting them, and works with leadership to advance the strategic vision and deliver day-to-day results.

The team is undergoing a digital transformation and works collaboratively across functions, using both legacy and new technologies. The position partners with internal stakeholders and external distribution partners to support underwriting quality, customer experience, talent development, and continuous improvement. Candidates residing within 50 miles of the Springfield, Massachusetts office are expected to work a hybrid schedule of three days per week in the office.

MassMutual describes the role as offering clear ownership and accountability, a collaborative environment, access to learning and development, internal networks, and employee-led communities. Compensation is listed at $144,800–$190,000, with incentive and bonus opportunities. The company also refers applicants to its Total Rewards at a Glance for information about benefits.

Requirements

• High school diploma.
• At least 7 years of disability underwriting experience.
• At least 2 years of experience leading or mentoring production underwriters.

Nice To Haves

• 10 or more years of direct individual disability insurance underwriting experience with underwriting authority.
• 7 or more years of production underwriting experience.
• Individual disability insurance underwriting leadership experience.
• Bachelor’s degree.
• Experience leading a concierge service team.
• Experience driving innovation, brainstorming effectively, adopting new methods and processes, proactively seeking alternatives, articulating how ideas may work in a business environment, and using advanced critical-path thinking.
• Demonstrated knowledge of medical, non-medical, and financial risk selection.
• Proven partnership with sales, product, marketing, and compliance.
• Flexibility to travel and work outside standard office hours.

Responsibilities

• Acquire, retain, and develop individual disability insurance underwriting talent.
• Lead, guide, mentor, and coach disability underwriters in technical and professional skills.
• Promote continuous improvement and root-cause problem-solving.
• Support an exceptional customer experience for career advisors and brokers.
• Work with Compliance, Legal, and underwriting partners on underwriting policies and new regulatory issues or inquiries.
• Maintain awareness of medical, financial, and occupational underwriting developments across the industry.
• Perform trending and root-cause analysis to identify gaps and recommend training needs or procedural changes.
• Develop and maintain relationships with General Agents, advisors, brokerage directors, and firm staff to resolve escalations, discrepancies, or risk-related concerns.
• Consider total case financials, relationships, and customer value when addressing underwriting matters.
• Work with leadership to develop and deliver on the department’s strategic vision and day-to-day results.
• Provide support to help the team meet department service-level requirements.
• Give and receive constructive feedback, adapt to change, and make behavioral changes based on feedback or experience.

Benefits

• Competitive salaries with incentive and bonus opportunities.
• Access to learning, development, and internal networks.
• Employee-led communities and forums that foster connection, learning, and inclusion.
• Industry-leading pay and benefits, with further details referenced through MassMutual’s Total Rewards at a Glance.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: High school or GED