Job Description:

Sun Life embraces a hybrid work model that balances in-office collaboration with the flexibility of virtual work in the contiguous states plus AK.

The opportunity: Are you a strategic underwriting leader who thrives in a collaborative, high-impact environment? We are seeking an Associate Director, Underwriting for our Medical Stop Loss insurance business. In this key leadership role, you’ll lead a multi-site team of experienced Stop Loss underwriters. You’ll work closely with the Director of Stop Loss Underwriting to drive new business strategies, support pricing and product innovation, and contribute to the success of our Stop Loss business at both regional and national levels.

You’ll bring strong technical underwriting expertise and a natural ability to build relationships—most notably with our Stop Loss Sales. Actuarial and Advanced Analytics partners—to help shape the future of our business.

How you will contribute:

• 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 will bring with you:

• Ability to work with a diverse range of people
• 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.

Salary: 

$114,300-$171,500

At our company, we are committed to pay transparency and equity. The salary range for this role is competitive nationwide, and we strive to ensure that compensation is fair and equitable. Your actual base salary will be determined based on your unique skills, qualifications, experience, education, and geographic location. In addition to your base salary, this position is eligible for a discretionary annual incentive award based on your individual performance as well as the overall performance of the business. We are dedicated to creating a work environment where everyone is rewarded for their contributions.

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