Advanced Markets Underwriting Director - Winnipeg - Dayforce HCM

Description

Posted Wednesday, February 25, 2026 at 5:00 AM

At Equitable, we believe work should be a place where you feel supported, inspired, and empowered to grow. In our caring and collaborative environment, your curiosity is encouraged, your passion is recognized, and your contributions truly matter. Together, we create meaningful impact, for our clients, our communities, and each other.

The Opportunity : At Equitable, we believe great things happen when we work together. We're a Canadian mutual company driven by purpose - putting people first and helping Canadians protect today and prepare for tomorrow. If you're passionate about making a difference and growing your career in an inclusive and collaborative environment, we'd love to hear from you. Our culture is built on care, passion and curiosity. We put people above all else, strive to be our best and welcome new ideas to deliver positive outcomes.

In this role, you will take case-level ownership of Advanced Markets files up to $200M, holistically assessing complex insurance structures, medical information, and financial scenarios to determine appropriate risk classifications. You will also serve as a mentor and informal leader within the Underwriting team, sharing expertise on advanced market cases and supporting the development and succession of critical technical knowledge. This position requires exceptional communication and case‑management skills, balancing a strong client‑focused approach with sound, risk‑appropriate underwriting decisions that maintain Equitable's competitive position in the market.

Join one of the region's top employers and be part of something that truly makes a difference.

Work Arrangements: You will work from your home office 100% of the time. You may be required to be in-person at our office in Waterloo, ON or another assigned location within the Waterloo Region, on an as needed basis. Sales related roles may be required to travel based on the assignment.

What you'll do:

- Underwrite complex UHNW cases by reviewing and analyzing medical, personal, legal, and financial information, assessing risks on applications with face amounts up to $200M.
- Deliver a high‑touch, concierge‑level experience to UHNW clients while ensuring underwriting decisions align with Equitable's pricing and risk philosophy.
- Build and maintain exceptional relationships with Advisors, their teams, and external professionals such as family office and client service teams.
- Develop strong partnerships with Distribution and internal colleagues to support seamless, client‑focused underwriting outcomes.
- Negotiate effectively with reinsurers, pricing, vendors, and internal partners to deliver competitive decisions and optimal solutions for the client, Equitable, and reinsurers.
- Ensure timely turnaround and uphold service standards for all UHNW underwriting activities.
- Act as a steward of the UHNW business by identifying risks, collaborating with senior leadership and technical experts, and ensuring sound risk assessment.
- Partner with the Technical Risk Team, Compliance, Claims, Legal, and Operations on complex cases and specialized underwriting considerations.
- Contribute to a positive team environment through active participation, knowledge sharing, mentorship, case clinics, and continuous development initiatives.
- Monitor industry trends and evolving underwriting practices, sharing insights and recommendations with the Chief Underwriter and senior leadership.

What you'll bring:

- A minimum of 10 years as an Individual Underwriter with Advanced Markets experience.
- Deeply understands the market, has awareness of trends and emerging risks, and brings forward recommendations, helping to maintain profitable mortality & morbidity experience.
- Expertise in compliance, claims, rescission, fraud, and legal implications associated with underwriting.
- Expert knowledge/experience in all aspects of risk assessment: medical, non‑medical, foreign travel, financial underwriting principals.
- Expert knowledge of retention management.
- Expert knowledge of the reinsurance marketplace.
- Delivers competitive underwriting decisions while balancing solid risk assessment.
- Ability to anticipate, negotiate, and drive outcomes through a client‑first mindset.
- Proven leadership and or mentorship experience in developing underwriters, especially in the Large Case space.
- Proficiency in assessing risk and applying guidelines with exceptional analytical, judgement and problem‑solving skills.
- Collaborative to forge partnerships with advisor and distribution teams.
- Drive toward client‑focused outcomes with an ability to identify and appropriately mitigate risks in a multi‑market/segment business.
- Has an entrepreneurial spirit and possess the communication skills and confidence to engage with senior level clients and colleagues.
- Self‑sufficient and resourceful professional who demonstrates flexibility and efficient time management skills.
- Strong presentation and influencing skills with the ability to represent our underwriting expertise and build trusted relationships.
- Mentor, develop, and inspire less experienced underwriters, ensuring continuity of expertise and readiness of future talent.
- Working toward or completion of FALU, FLMI, and ACS.

What's in it for you:

- Career Growth: Regular learning sessions and development opportunities.
- Total Rewards: Incentive pay, annual salary reviews, employer‑paid benefits and pension matching.
- Time Away: Competitive vacation plus one paid volunteer day each year.
- Flexibility: Healthy work‑life balance with employee wellness always top of mind, complemented by a "dress for your day" approach.

At Equitable, we're committed to fair pay and an inclusive, accessible hiring experience. If you need accommodations or alternative formats at any stage, just reach out to us at careers@equitable.ca. We're happy to help.

Your base pay will be based on your skills, qualifications, experience and education. In addition to your salary, this role is eligible for a discretionary annual incentive award tied to business performance, plus a wide range of competitive benefits.

If you're selected to move forward, our Talent Acquisition team will walk you through all the details of our total rewards program, so you know exactly what's included.

Reports To: Underwriting and Claims Vice President

Department: Individual Insurance

Term: Permanent Full-Time

This position is open and we are excited to find the right person to join our team.

As part of the recruitment process, you will need to go through background screening, as per our company policy.

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