Associate Director, Underwriting

Sun Life U.S. is one of the largest providers of employee and government benefits, helping approximately 50 million Americans access the care and coverage they need. Through employers, industry partners and government programs, Sun Life U.S. offers a portfolio of benefits and services, including dental, vision, disability, absence management, life, supplemental health, medical stop-loss insurance, and healthcare navigation. We have more than 6,400 employees and associates in our partner dental practices and operate nationwide. Visit our website to discover how Sun Life is making life brighter for our customers, partners and communities. 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. Not ready to apply yet but want to stay in touch? Join our talent community to stay connected until the time is right for you! We are committed to fostering an inclusive environment where all employees feel they belong, are supported and empowered to thrive. We are dedicated to building teams with varied experiences, backgrounds, perspectives and ideas that benefit our colleagues, clients, and the communities where we operate. We encourage applications from qualified individuals from all backgrounds. Life is brighter when you work at Sun Life At Sun Life, we prioritize your well-being with comprehensive benefits, including generous vacation and sick time, market-leading paid family, parental and adoption leave, medical coverage, company paid life and AD&D insurance, disability programs and a partially paid sabbatical program. Plan for your future with our 401(k) employer match, stock purchase options and an employer-funded retirement account. Enjoy a flexible, inclusive and collaborative work environment that supports career growth. We’re proud to be recognized in our communities as a top employer. Proudly Great Place to Work® Certified in Canada and the U.S., we’ve also been recognized as a "Top 10" employer by the Boston Globe's "Top Places to Work" for two years in a row. Visit our website to learn more about our benefits and recognition within our communities. We will make reasonable accommodations to the known physical or mental limitations of otherwise-qualified individuals with disabilities or special disabled veterans, unless the accommodation would impose an undue hardship on the operation of our business. Please email View email address on click.appcast.io to request an accommodation. For applicants residing in California, please read our employee California Privacy Policy and Notice. We do not require or administer lie detector tests as a condition of employment or continued employment. Sun Life will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requirements of applicable state and local laws, including applicable fair chance ordinances. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. Job Category: Underwriting - Group Posting End Date: 19/07/2026 Shine together At Sun Life, you can be your most brilliant self. Our supportive, flexible, and inclusive work environment is one where you – and your career – can thrive. Whatever your aspirations, collaborative leaders and colleagues are ready to help you learn, grow, and succeed. Make life brighter We’re a global company with a passion for people. Our purpose is to help Clients achieve lifetime financial security and live healthier lives. As a team of 30,000 across 26 countries, our impact is far-reaching, and locally relevant There’s power in numbers. As part of Sun Life’s growing team, you have an impact on people in your community and around the world. Shape the future With an optimistic eye on a brighter future, we drive to innovate. Be part of leading change, push boundaries and try new ways of working. Use data to drive bold actions. Be agile and pivot as we test and learn. At Sun Life, we’re driving transformation, sustainability and innovation for our Clients, employees, partners, and communities. Join us. Together, we can make the future brighter. Join a top employer for a brighter future. Visit Sun Life Careers