Manager, Underwriting Operations, Commercial Mid-Market - Ontario

Wawanesa Insurance•Toronto, ON

2d•CA$130,000 - CA$150,000•Hybrid

About The Position

The Manager, Underwriting Operations, Commercial Mid-Market - Ontario is responsible for leading and developing a team of Commercial Mid-Market Underwriters while driving profitable growth, underwriting quality, and strong broker relationships across Ontario. This highly visible, market-facing leadership role combines people leadership, technical underwriting expertise, and business development support to strengthen Wawanesa's presence in the Ontario market. Working closely with Business Development, Claims, Risk Prevention Services, Product, and Pricing, the Manager coaches underwriting talent, supports complex risk decisions, builds strategic broker partnerships, and ensures consistent execution of underwriting and growth strategies.

Requirements

8-10+ years of Commercial Underwriting experience, including significant Mid-Market expertise.
Demonstrated leadership capability with a strong passion for coaching, mentoring, and developing underwriting talent.
Strong technical knowledge of Commercial Property and Casualty risks, portfolio management, and underwriting authorities.
Proven ability to balance profitable growth with disciplined underwriting practices.
Strong broker relationship management, business development, and stakeholder engagement skills.
Excellent communication, negotiation, and leadership abilities.
CIP designation required
Willingness to travel throughout Ontario and occasionally nationally.

Nice To Haves

FCIP, CRM, or MBA considered assets.

Responsibilities

Lead, coach, and develop a high-performing underwriting team through regular coaching, file reviews, performance management, and talent development initiatives.
Provide technical oversight on complex commercial risks, underwriting referrals, exceptions, and authority decisions while ensuring alignment with underwriting appetite and profitability objectives.
Build and maintain strong broker relationships, participate in broker-facing meetings and growth initiatives, and represent Wawanesa as a trusted market leader throughout Ontario.
Support profitable growth by partnering with Business Development on new business opportunities, targeted industries, and key broker relationships.
Monitor portfolio performance, underwriting quality, and service standards, identifying trends and implementing corrective actions where required.
Partner with internal stakeholders to execute commercial strategies, support underwriting and pricing initiatives, and contribute market insights to business decisions.
Champion operational excellence, continuous improvement, regulatory compliance, and an exceptional broker experience.