Sign up to access all features of our service.
  • Job search
  • Favorites
  • Create a CV
    New
  • Salaries
  • Subscriptions

Associate Director, Underwriting

$114.3k - $171.5k

Sun Life

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 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:

29/06/2026
Vacancy posted 9 hours ago
Similar jobs that could be interesting for youBased on the Associate Director, Underwriting in Portland, ME vacancy
  • $103k - $154.5k

     ...We have more than 6,400 employees and associates in our partner dental practices and operate...  ...The Opportunity: The Associate Director LTD Claims is leadership role offers the...  ...with internal parties, including underwriting, distribution, and legal compliance.... 
    Suggested
    Work at office
    Local area
    Flexible hours
    2 days per week

    Sun Life

    Portland, ME
    3 days ago
  • $137k - $235.75k

     ...while championing patients every step of the way. Learn more at We are searching for the best talent for the role of Associate Director, Oncology Epidemiology . We have a preference for this position to be located in either Raritan, NJ or Horsham, PA. Remote work... 
    Suggested
    Full time
    Temporary work
    Local area
    Remote work

    Johnson & Johnson

    South Portland, ME
    3 days ago
  • $4,000 per month

     ...Job Description Job Description About the Job... We're looking for an Associate Creative Director with an art background who is ready to stop being “almost there.” You're past the part where potential is enough. You believe in your work and you're learning how... 
    Suggested
    Work at office
    Monday to Thursday

    VIA

    Portland, ME
    15 days ago
  • $90k - $100k

     ...Job Type Full-time Description Job Title: Associate Director of Development, Institutional Giving Supervisor: Chief Development Officer Starting Salary Range: $90,000-$100,000 Overview: The Gulf of Maine Research Institute (GMRI) develops... 
    Suggested
    Full time
    Work at office
    Immediate start
    Flexible hours

    Gulf of Maine Research Institute

    Portland, ME
    4 days ago
  •  ...trained, full-time surgical oncologist to join its well-established team in Portland, Maine, with the potential to become the Associate Medical Director of General Surgical Oncology and Endocrine Surgery. The surgeon will be expected to have a track record of clinical... 
    Suggested
    Full time
    Local area
    Immediate start
    Relocation package

    Maine Medical Center

    Portland, ME
    3 days ago
  • $100k - $130k

     ...Associate Product Manager The Associate Product Manager will support the end-to-end management of assigned product lines, ensuring strong operational execution, cross-functional alignment, and continuous product improvement. This role is responsible for monitoring product... 
    Work at office
    Remote work
    Flexible hours

    Nova Biomedical

    Westbrook, ME
    9 hours ago
  • Cheez is a new app that sends you the pictures that your friends take of you, powered by facial recognition. See the iOS app or the Android app Responsibilities: Assist in defining product requirements, objectives, and key results based on user needs and market...
    Full time

    Cheez

    South Portland, ME
    3 days ago
  • $50k - $65k

     ...Experience an area of great opportunity for potential candidates. What will you be doing? World Wide Technology is seeking an Associate Customer Onboarding Manager to facilitate onboarding and software lifecycle activities for customers engaged in recurring revenue... 
    Full time
    Contract work
    Remote work
    Shift work

    World Wide Technology

    Portland, ME
    4 days ago
  • $20.41 - $40.36 per hour

     ...part of a company where your voice matters, your work has purpose, and your potential has no limits — HUB is the place for you. Associate Account Executive We currently have an opportunity for an Associate Account Executive to join our Small Business Commercial... 
    Work at office
    Local area

    Squaremouth

    South Portland, ME
    2 days ago
  • $147.1k - $220.7k

     ...products for many top Fortune 500 companies. Prudential has been underwriting group insurance plans since 1916. Today, our Group Insurance...  ...directly to the Head of Supplemental Health Underwriting, the Director, Operational Excellence will direct the process analysis,... 
    Full time
    Part time

    Prudential Financial

    Portland, ME
    2 days ago
  •  ...Company: Marsh McLennan Agency Description: Associate Consultant, Employee Health & Benefits Our not-so-secret sauce....  ...relationships Identify and understand negotiable elements of underwriting calculations for all lines of coverage. Manage post-... 
    Local area
    Night shift

    Marsh McLennan

    Portland, ME
    2 days ago
  •  ...and budget. Present products through Zoom calls to guarantee understanding for each client Complete applications and meet underwriting requirements efficiently. Handle various administrative tasks related to client accounts ~18 years of age or older ~ Passion... 
    Full time
    Remote work

    Zuzick Organization of Globe Life

    South Portland, ME
    4 days ago
  •  ...of others while personally thriving! Join Bridge Senior Living – a certified Great Place to Work (2025-2026)! Now Hiring! Care Associate Shifts: 6a-2p or 2p-8p! Qualifications of an ideal Care Associate: High school diploma or equivalent (GED) CNA or HHA in... 
    Work experience placement
    Local area
    Immediate start
    Shift work

    The Enclave Of Scarborough

    Scarborough, ME
    5 days ago
  •  ...Hartford, CT, Denver, CO, Moorpark, CA, or Portland, ME Korn Ferry has partnered with our client on their search for the role, Director, AI Enablement. Purpose of the Position The Director – AI Enablement is responsible for translating emerging AI capabilities... 
    Work at office
    Immediate start

    Korn Ferry

    Portland, ME
    3 days ago
  •  ...Director of Rehabilitation (Director of Rehab) We are seeking an experienced and motivated Director of Rehabilitation to oversee daily operations of rehabilitation services, including physical, occupational, and speech therapy programs. The Director will lead therapy... 

    Medcadre Inc

    Scarborough, ME
    2 days ago
  •  ...Director Of Pharmacy New England Life Care (NELC) is one of the fastest growing home infusion therapy services companies in New England and is the region's only non-profit home infusion provider. NELC is a hospital collaborative serving more than 70 hospital systems... 
    Full time
    Temporary work
    Work at office
    Local area
    Monday to Friday
    Weekend work

    New England Life Care

    Scarborough, ME
    1 day ago
  • $155.3k - $213.51k

     ...Director, Labor Relations location: PORTLAND, OR, US, 97232 | SALT LAKE CITY, UT, US, 84116 Company: PacifiCorp POWER YOUR GREATNESS PacifiCorp is seeking customer-centric candidates to grow and sustain our commitment to a culture of customer service... 
    Full time
    Contract work
    Temporary work
    Local area

    PacifiCorp Careers

    Portland, ME
    3 days ago
  • $33 - $46 per hour

     ...Job Description Job Description Position: Director of Rehab Salary Range: $33-46 per hour (depending on discipline) a reputable 60-bed skilled nursing facility, is seeking a highly qualified and experienced Director of Rehab to join our team. This is a full-time... 
    Hourly pay
    Full time
    Temporary work
    Monday to Friday
    Weekend work

    Trinity Healthcare Talent Services

    Scarborough, ME
    18 days ago
  •  ...time and critically think and react quickly in emergent situations, above average manual dexterity, independent decision making associated with accepted practice in clinical perfusion, strong ability to anticipate and solve life threatening perfusion problems. 4) Pediatric... 
    Immediate start
    Flexible hours

    Maine Medical Center

    Portland, ME
    1 day ago
  • $33 - $50 per hour

    10% Salary placement fee Salary range: $33 - $50 40 hours Monday - Froday Cannot take new Can accept any discipline (PT, OT, SLP, PTA, OTA) 60-bed skilled nursing facility, offering short-term rehab, LTC and respite care.
    Permanent employment
    Temporary work

    Carenest Health Services

    Scarborough, ME
    3 days ago
  • $80k

     ...Senior Organizing and Political Director The Maine Democratic Party (MDP) is seeking a seasoned senior operative to serve as the Senior Organizing and Political Director, responsible for developing and overseeing the Party's statewide political, organizing, and down... 
    Full time
    Temporary work
    Work at office
    Local area
    Relocation package

    Arena

    Portland, ME
    4 days ago
  • $40 - $50 per hour

     ...Program, and expand your expertise with our Clinicians in Action professional development program. Responsibilities: The Senior Director of Rehab (Sr. DOR) is responsible for the efficient and profitable management of rehabilitation services in their assigned... 
    Full time
    Part time
    H1b
    Work from home
    Visa sponsorship
    Relocation package

    PowerBack Rehabilitation

    Westbrook, ME
    3 days ago
  •  ...Job Description Job Description Job Title: Associate Veterinarian Location: Multiple Opportunities Available Nationwide Job Description Aeries Recruiting partners with privately owned veterinary practices across the United States that are actively seeking... 
    Flexible hours

    Aeries Recruiting LLC

    Portland, ME
    23 days ago
  • $58.8k - $88.2k

     ...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... 
    Work at office
    Local area
    Flexible hours
    Night shift

    Sun Life

    Portland, ME
    9 hours ago
  •  ...Cruise & Excursions Director American Cruise Lines, the largest USA flagged cruise line in the United States, is looking to add Cruise & Excursions Directors to our shipboard team for our 2026 season. American Cruise Lines only operates within the United States and has... 
    Daily paid
    Full time
    Work at office
    Local area
    Immediate start
    Home office
    Shift work
    Day shift

    American Cruise Lines

    Portland, ME
    1 day ago
  • $185k - $220k

     ...Job Summary The Director, Medical Affairs (Nutrition) is responsible for leading and managing medical affairs for approved nutrition...  ...enable comprehensive scientific exchange around disease states and associated Company products. Must maintain scientific expertise in the... 
    Permanent employment
    Work at office
    Night shift

    DiversityJobs Inc

    Portland, ME
    5 days ago
  • $150k - $175k

     ...passionate,diverseand dedicated employees who work together to achieve uncommon results. Job Summary We are seeking a Director, AI Enablement to lead the adoption and application of AI across our enterprise. This role is focused on using tools like ChatGPT... 

    Ensign-Bickford Industries

    Portland, ME
    3 days ago
  •  ...Full-Time Kitting Associate at Sea Bags Sea Bags, the original maker of one-of-a-kind totes, handbags, and accessories crafted in the USA from recycled sailboat sails, is looking for a Full-Time Kitting Associate who plays a vital role in coordinating and assembling... 
    Full time
    Temporary work
    Flexible hours
    Shift work

    Sea Bags, LLC

    South Portland, ME
    5 days ago
  • Walmart Stores | Medical, Dental, Vision, Rx + 401(k) with match + PTO + 100% Reimbursement of Tuition & Books | 500 Gallery Boulevard | Responsibilities: Fill and dispense online orders; Locate, prepare, and package merchandise; Ensure accuracy of orders prior to pick...
    Immediate start

    Wal-Mart Stores , Inc.

    Scarborough, ME
    4 days ago
  •  ...make your mark with the world's largest equipment rental provider, come build your future with United Rentals! As an Equipment Associate at United Rentals, you will perform a variety of manual tasks to ensure smooth branch operation. Your primary objective will be to... 
    Hourly pay

    American Rental Association

    Westbrook, ME
    9 hours ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Associate Director, Underwriting. Be the first to apply!