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Bilingual Director, Advanced Underwriting - Mentorship

Remote / Online - Candidates ideally in
Winnipeg, Manitoba, A3C, Canada
Listing for: Sun Life
Remote/Work from Home position
Listed on 2026-08-18
Job specializations:
  • Insurance
    Underwriter, Insurance Analyst
Salary/Wage Range or Industry Benchmark: 110000 - 180000 CAD Yearly CAD 110000.00 180000.00 YEAR
Job Description & How to Apply Below

You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager to share their knowledge with you. Your leaders will inspire and help you reach your potential and soar to new heights. Every day, you'll have new and exciting opportunities to make life brighter for our Clients - who are at the heart of everything we do.

At Sun Life, we're driven by our

Purpose:

helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring, and impactful.

When you join Sun Life, you'll work with passionate colleagues and empowering leaders who support your growth and celebrate your contributions, so you can make a meaningful difference in our Clients' lives.

Discover how you can make a difference in the lives of individuals, families and communities around the world.

Job Description Location

Hybrid, Work from Home

As a Director, Advanced Underwriting
- Mentorship, you’ll be joining one of Canada’s top insurers. We’re known for not only our strength in the market, but our commitment to our people. Underwriting goes beyond risk assessments here. We’re focused on making thoughtful, well-informed decisions that provide financial security to Canadians and their loved ones.

By joining Sun Life, you become part of a high-performing team, led by passionate professionals with extensive experience in the field, industry knowledge, and a passion for mentorship. Our continuous learning pathways and skills development opportunities ensure endless growth for you as you advance in your career.

This role will be reporting to our Chief Underwriter and Claims Risk Officer. We’re looking for an experienced underwriter with a passion for mentoring others and expertise in ultra-high net worth cases (>$25M). You’ll partner with specialized case managers, advisors, reinsurance partners, and business leaders to assess medical, personal, and financial risk up to $200 million. A commitment to Client-first, proactive communication and partnership with our advisors and distribution team are critical aspects to this role.

What

will you do?
  • Analyze insurance applications and evidence of insurability
  • Apply holistic underwriting expertise in all areas of underwriting (including medical, financial and lifestyle factors) to make sound and competitive underwriting decisions
  • Negotiate decisions with our reinsurers, in accordance with reinsurance treaties and internal rules
  • Effectively communicate and explain decisions to advisors and/or Clients’ physicians, as required
  • Build strong relationships with business leaders, distribution teams, and advisors while delivering exceptional service and expertise
  • Identify continuous improvement opportunities and bring forward recommendations for solutions
  • Contribute to a positive environment through teamwork, a spirit of innovation, and professional development
  • Attend and contribute to regular HNW case reviews to share knowledge and support team development
  • Mentor and help employees reach the next levels in their careers
What do you need to succeed?
  • Decision Making Authority >$10,000,000 for Life and $1,000,000 of Critical Illness
  • Exceptional analytical, judgement, problem-solving and decision-making skills
  • Client and results focused, with proactive service orientation to support our business goals
  • Ability to influence and negotiate
  • Strong knowledge of medical and financial risk factors
  • The ability to work in a fast-paced environment, meet tight deadlines, and balance completing priorities
  • Interpersonal skills to work collaboratively with our internal and external partners
  • Strong attention to detail and accuracy
  • Ability to work independently and eager to take on responsibility
  • 10-15 years of experience as an Individual Life Underwriter
  • Bachelor's degree or equivalent
  • Specialized training: ALU certificate and commitment to ongoing education with a goal of attaining the Fellow, Academy of Life Underwriting (FALU) and Fellow, Life Management Institute (FLMI) designations
  • Bilingualism (French, English, both…
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