Trevor Miles
Winnipeg,MB
Summary
Accomplished insurance leader with a strong focus on building effective broker partnerships and team engagement. Known for developing senior relationships that shape market strategy and drive profitability across diverse portfolios.
Overview
1
1
Certification
2027
2027
years of professional experience
Work History
ASSISTANT VICE PRESIDENT, COMMERCIAL INSURANCE
Definity Insurance
2026 - Current
- Led a commercial insurance organization of approximately 60 employees, including frontline leaders and managers.
- Oversaw growth, underwriting performance, and P&L for southwestern Ontario transportation and national farm portfolio, driving profitability.
- Managed Ontario transportation portfolio, enhancing fleet and cargo coverage for long-haul risks with U.S. exposure.
- Provided national leadership and strategic direction for farm, overseeing underwriting execution and broker relationships.
- Achieved retention near 90%, maintaining rate and underwriting discipline while increasing new business activity.
- Developed senior relationships with key broker partners to shape market strategy and guide business planning.
MANAGING ACCOUNT EXECUTIVE – MIDDLE MARKET
Travelers Canada
2018 - 2026
- Enhanced relationships with key broker partners nationally, aligning distribution strategy with growth and profitability objectives to support regional success.
- Directed managers and underwriting teams across Canada, ensuring profitable growth and execution of regional business plans.
- Cultivated high-performing teams through coaching, succession planning, recruitment, performance management to drive team effectiveness.
- Sustained team engagement during market cycles and organizational change while maintaining underwriting discipline and customer service to ensure consistent service delivery.
MANAGING ACCOUNT EXECUTIVE – MIDDLE MARKET
Travelers Canada
Winnipeg
2013 - 2018
- Established performance-oriented culture prioritizing underwriting excellence and fostering strong broker partnerships.
- Led underwriting team in Winnipeg for Manitoba and Saskatchewan, enhancing coaching effectiveness and optimizing portfolio management.
- Developed employee programs to support professional growth and strengthen team capabilities.
COMMERCIAL LINES CASUALTY SPECIALIST
Aviva Insurance Company of Canada
2011 - 2013
- Drove profitable growth of branch casualty portfolio, collaborating with senior leadership and underwriters on complex referrals and underwriting strategy.
COMMERCIAL LINES UNDERWRITER
Aviva Insurance Company of Canada
2003 - 2011
- Underwrote new and renewal commercial business, ensuring alignment with regional risk factors in Manitoba and Saskatchewan.
Education
Business Administration Diploma - Accounting Major
Red River Community College
WinnipegSkills
- Underwriting execution
- Market analysis
- Portfolio management
- Profitability analysis
- Risk assessment
- Market analysis
- Strategic planning
- Change management
- Performance management
- Team leadership
- Change management
Certification
- CIP Designation
Timeline
ASSISTANT VICE PRESIDENT, COMMERCIAL INSURANCE
Definity Insurance
2026 - Current
MANAGING ACCOUNT EXECUTIVE – MIDDLE MARKET
Travelers Canada
2018 - 2026
MANAGING ACCOUNT EXECUTIVE – MIDDLE MARKET
Travelers Canada
2013 - 2018
COMMERCIAL LINES CASUALTY SPECIALIST
Aviva Insurance Company of Canada
2011 - 2013
COMMERCIAL LINES UNDERWRITER
Aviva Insurance Company of Canada
2003 - 2011
Business Administration Diploma - Accounting Major
Red River Community College