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Added 44 mins ago
Financial Advisor
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Full-time
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Manager, Retirement & Savings Advice and Sales - Rollover
Canada Life
Winnipeg, MB
Full-time
The Manager is responsible for achieving team sales, retention, productivity and client experience objectives through strong leadership, operational excellence and disciplined management of…
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Manager, Retirement & Savings Advice and Sales - Rollover
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HDI Global SE

Executive Underwriter, Mid-Market

Toronto, ON, Canada

Job type: Full-time
Apply by: Mar 21, 2027
Education: Bachelor’s degree
Experience: 5+ years of property and casualty underwriting experience, including complex mid-market risks.
Posting language: English
Posted: Sep 22, 2026

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Original job description

Functional Area: Mid-Market Underwriting

Travel: As required

We are seeking a driven underwriting professional with 5+ years of experience to join our growing team in Canada as an Executive Underwriter, Mid-Market. Reporting to the Head of Mid-Market, the successful candidate will underwrite complex and strategic risks, strengthen broker and client relationships, and contribute to the growth, profitability, and long-term success of the Mid-Market portfolio.

This is an exciting opportunity for a seasoned underwriter who thrives in a technical, relationship-driven role. As a trusted expert and business partner, you will help influence underwriting strategy, support portfolio performance, mentor colleagues, and contribute to the future direction of our Mid-Market business.

About Us

HDI Global SE delivers a comprehensive service-based offering to the commercial and specialty insurance markets. Our strategy is to create sustainable growth and build a robust company that operates successfully worldwide. Our highly competent team is committed to delivering market-leading insurance solutions.

We are part of the Talanx Group, one of the major European insurance groups, with insurance revenue of EUR 49.0 billion (2025), and more than 120 years of experience in industrial insurance. HDI Global SE operates in more than 175 countries across the globe with over 5,500 employees worldwide. Financial strength ratings: AM Best A+ (Stable), Standard & Poor’s AA- (Very Strong, Outlook Stable).

At HDI, we offer employees the advantages of an international organization within a modern, dynamic work environment in the heart of downtown Toronto that both challenges and rewards. We foster strong communication and achieve our objectives through our core values of Together, Ownership, and Performance. Employees are encouraged to contribute their ideas and play an active role in shaping our company’s future.

Your Responsibilities

Lead underwriting of complex new and renewal mid-market risks within established authority and risk appetite.
Build, manage, and grow a profitable portfolio of business, maintaining accountability for growth, retention, underwriting quality, and profitability.
Build and maintain strategic broker and client relationships, serving as a trusted advisor on complex underwriting matters.
Contribute to the development of underwriting appetite, portfolio initiatives, and distribution strategies.
Represent the organization in broker and client meetings, negotiations, industry events, conferences, and networking activities to strengthen relationships and enhance market visibility.
Ensure high standards of governance, including accuracy of underwriting files, policy documentation, data quality, and compliance with internal and regulatory requirements.
Act as a senior technical referral authority for complex risks, providing guidance on underwriting structure, pricing, coverage solutions, and risk selection.
Provide coaching, technical mentorship, and underwriting leadership to team members, supporting talent development and underwriting excellence.
Contribute to portfolio reporting, business planning, and strategic initiatives in support of organizational objectives.

Your Profile (Skills, Qualifications & Experience)

5+ years of property and casualty underwriting experience, including complex mid-market risks.
Advanced expertise in property and casualty policy wordings, underwriting, pricing, and risk assessment.
Demonstrated ability to make sound underwriting decisions, manage portfolio performance, and drive profitable growth.
Proven leadership and technical expertise, with the ability to mentor, influence, and develop underwriting talent.
Entrepreneurial and results-oriented, with proven track record in broker relationship management, business development, and profitable portfolio growth.
Bachelor's degree and CIP designation are required; FCIP designation is preferred.
Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment.
Exceptional negotiation, analytical, and problem-solving skills, combined with strong commercial acumen.
Excellent oral and written communication skills in English.
Working knowledge of French and/or German is considered an asset.
Proficiency with underwriting systems and Microsoft Office applications.
Ability to work independently in a fast-paced, results-driven environment while balancing strategic priorities and execution.
Occasional travel to key markets is expected.

What We Offer

Salary range is $100,000-$140,000, plus bonus opportunity.
Competitive total rewards package and professional development support
Flexible Working Hours
Competitive Time Off Policy
International Network
External Education & Tuition Reimbursement Program
Hybrid Work Environment
Comprehensive Health & Dental Benefits
Employer-Matched RRSP Contributions
Employee Share Purchase Program

Privacy

Visit: https://www.hdi.global/en-ca/legal/privacy for information on how we may collect, use or disclose your personal information.

Accessibility

HDI Canada Branch welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

We welcome applications from motivated, team-oriented individuals who are eager to take on new challenges.

Thank you to all applicants for their interest. Please note that only candidates selected for an interview will be contacted.

Apply About employer

More about this job

Responsibilities

The Executive Underwriter will lead the underwriting of complex mid-market risks while managing a profitable portfolio and strengthening broker relationships. They will also provide technical mentorship to team members and contribute to the development of underwriting strategies and portfolio performance.

Requirements

Candidates must have at least 5 years of property and casualty underwriting experience with expertise in complex mid-market risks. A bachelor's degree and CIP designation are required, with strong negotiation, analytical, and leadership skills.

Skills

Underwriting
Risk assessment
Portfolio management
Business development
Technical mentorship
Strategic planning
Negotiation
Analytical skills
Problem-solving
Commercial acumen
Policy wording
Pricing
Data quality
Regulatory compliance

Benefits

Bonus opportunity
Professional development support
Flexible working hours
Competitive time off policy
International network
External education and tuition reimbursement program
Hybrid work environment
Comprehensive health and dental benefits
Employee share purchase program

Visa sponsorship

Not detected in the job text

Keywords

Underwriting
Mid-Market
Property and Casualty
Risk Assessment
Portfolio Management
Broker Relations
Business Development
CIP Designation
FCIP
Insurance
Strategic Planning
Pricing
Policy Documentation
Governance
Mentorship
Commercial Insurance
Risk Appetite
Data Quality
Regulatory Compliance
Negotiation

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