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Technical Underwriter Small Group Insurance Jobs in Toronto

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Active Technical Underwriter Small Group Insurance roles in Toronto, indexed directly from company ATS systems — not reposted from LinkedIn, Indeed, or Glassdoor. Upload your resume to see your match score against open positions.

Surety - Underwriter - Commercial and Small Contract

The Cincinnati Insurance Companies

Surety - Underwriter - Commercial and Small Contract Hybrid Direct
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Senior Insurance Specialist

Mercedes-Benz Financial Services Australia

Australia-Victoria (Australia)-Mulgrave/Melbourne Flexible Senior Direct
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Property Underwriter

Hippo Insurance

Austin, Texas, United States Hybrid Direct
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Case Consultant (Group Insurance)

AU-VIC-Docklands Direct
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Excess & Surplus - Underwriter

The Cincinnati Insurance Companies

Excess & Surplus - Underwriter Flexible Mid Direct
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Underwriting Assistant

The Cincinnati Insurance Companies

Sales - Underwriting Assistant Onsite Direct
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Excess & Surplus - Underwriter

The Cincinnati Insurance Companies

Excess & Surplus - Underwriter Onsite Mid Direct
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Commercial Lines Underwriter

Auto-Owners Insurance

Charlotte, NC Remote Direct
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Excess & Surplus - Production Underwriter

The Cincinnati Insurance Companies

Excess & Surplus - Production Underwriter Flexible Senior Direct
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Underwriting Assistant

The Cincinnati Insurance Companies

Excess & Surplus - Underwriting Assistant Onsite Direct
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Underwriting Assistant

The Cincinnati Insurance Companies

Excess & Surplus - Underwriting Assistant Onsite Direct
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Senior Motor Fleet Underwriter

Flock

London Hybrid Senior Direct
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Underwriting Manager

The Cincinnati Insurance Companies

Sales - Underwriting Manager Onsite Manager Direct
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Corporate Business Development Manager (Group Insurance)

Multiple Locations Manager Direct
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Commercial Underwriter

EMC

United States of America Remote Direct
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Senior Mortgage Underwriter

Altisource

United States, UNITED STATES, United States Remote mid Direct
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Associate Underwriter

Gravie

Remote Remote Entry Direct
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Excess & Surplus - Production Underwriter

The Cincinnati Insurance Companies

Excess & Surplus - Production Underwriter Onsite Senior Direct
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Underwriter - New Business

ParetoHealth

Salt Lake City, Utah, United States Direct
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Regional Underwriting Manager

Converge Insurance

United States Manager Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Underwriter

Gravie

Remote Remote Direct
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Surety - Field Representative - Commercial and Small Contract

The Cincinnati Insurance Companies

Surety - Field Representative - Commercial and Small Contract Remote Direct
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Surety - Field Representative - Commercial and Small Contract

The Cincinnati Insurance Companies

Surety - Field Representative - Commercial and Small Contract Flexible Direct
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Renewable Energy Underwriter

Climate First Bank

United States - Remote Remote Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Senior Underwriter, Quality

AU-VIC-Docklands Onsite Senior Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Underwriting Assistant

Amwins Global Risks

22 Bishopsgate, London, EC2N 4BQ, United Kingdom Onsite Direct
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Personal Lines Underwriting Trainee

The Cincinnati Insurance Companies

Personal Lines - Underwriting Trainee June 2026 Onsite Entry Direct
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Small Projects Foreman

USA Mechanical & Energy Services

Hartford, Connecticut, United States Onsite Mid Direct
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Underwriter - New Business

ParetoHealth

Philadelphia, Pennsylvania, United States Hybrid Direct
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Commercial CAT Underwriting Manager (P&C Insurance)

US Remote Manager Direct
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Underwriting Manager

Sentry

Denver, CO Remote Manager Direct
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Senior Underwriter

Abound

Madrid Senior Direct
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Insurance Advisor

BESIX

Brussels, Brussels, BE Onsite mid Direct
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Insurance Advisor

BESIX

Brussels, Brussels, BE Onsite mid Direct
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Small Works Estimator

Dexterra Group

Mississauga, ON, Canada mid Direct
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Senior Underwriter

Abound

Madrid Senior Direct
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Senior Underwriter

Nirvana

Remote Remote Senior Direct
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Small Works Estimator

Dexterra Group

Mississauga, ON, Canada Onsite mid Direct
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Insurance Agent

Horace Mann

Nevada Flexible Direct
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Insurance Agent

Horace Mann

Arizona Flexible Direct
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Insurance Representative

Global Elite Empire Consultants

Andover, Minnesota Remote Direct
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Retail Credit - Senior Underwriter

Mercedes-Benz Financial Services

United Kingdom-England-Milton Keynes Flexible Senior Direct
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Underwriter

Starr

Chicago, IL Onsite Mid Direct
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Insurance Representative

Global Elite Empire Consultants

Fresno, California Remote Direct
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Common Questions

How many technical underwriter small group insurance jobs in toronto are available?
JobsGlitch lists active technical underwriter small group insurance jobs in toronto sourced directly from company ATS platforms — not reposted from LinkedIn.
Are these Technical Underwriter Small Group Insurance roles actually hiring in Toronto?
Yes — every listing is indexed directly from company career pages (Greenhouse, Lever, Workday, Ashby). These are not aggregated from other job boards, so they reflect live hiring intent.
What skills do Technical Underwriter Small Group Insurance jobs in Toronto require?
Required skills vary by employer and seniority. Browse the listings above to see the specific requirements for each open role.
How do I apply for technical underwriter small group insurance jobs in toronto?
Click any job listing to view the full description and apply directly on the company's career page. Upload your resume on JobsGlitch first to see your match score before applying.