Associate Director, Underwriting

Associate Director leading underwriting for Stop Loss insurance business. Collaborating with sales and analytics to drive strategy and success.

Posted 6/10/2026full-timeHartford • Connecticut, Kansas, Maine, Maryland • 🇺🇸 United StatesSenior💰 $114,300 - $171,500 per yearWebsite

Key responsibilities & impact

Lead and support a high-performing team responsible for underwriting and selling profitable Stop Loss business.
Partner with Actuarial, Underwriting and Advanced Analytics leadership to design and execute strategies aligned with business goals.
Build strong relationships with Sales and Distribution teams to support strategic growth and retention efforts.
Hire, develop, and retain top underwriting talent; foster a culture of learning, performance, and accountability.
Support in departmental and team projects.
Serve as a technical expert and advisor on complex underwriting cases.
Drive consistency and compliance in underwriting practices and procedures.
Support broker meetings and client engagements to help deliver Sun Life’s value proposition.
Continuously evaluate and improve underwriting approaches through training, quality reviews, and feedback loops.
Champion a high-performance culture through clear goals, accountability, and recognition.

What you’ll need

Bachelor’s degree preferred (or equivalent years of experience in the Stop Loss or related insurance industry)
5–10 years of underwriting experience, with a focus on Stop Loss
Proven leadership experience—preferably managing underwriters or underwriting teams
Experience navigating complex underwriting challenges and delivering strategic solutions
A strong background in underwriting operations, ideally within Stop Loss.
Excellent communication and collaboration skills with the ability to influence across teams.
Strategic thinking with a hands-on approach to execution.
Confidence in negotiating and presenting at a senior level.

Comp & perks

Generous vacation and sick time
Market-leading paid family, parental and adoption leave
Medical coverage
Company paid life and AD&D insurance
Disability programs
Partially paid sabbatical program
401(k) employer match
Stock purchase options
Employer-funded retirement account
Flexible, inclusive and collaborative work environment that supports career growth

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

underwritingStop Lossstrategic solutionsunderwriting operationscomplex underwriting challengesquality reviewstraining

Soft Skills

leadershipcommunicationcollaborationinfluencestrategic thinkingnegotiationpresentationaccountability

Certifications

Bachelor's degree