Senior Commercial Underwriter (Remote/Ontario) - Job #229

Our client is seeking an experienced Senior Commercial Underwriter to support the continued growth of its commercial insurance business in Ontario. This is a remote opportunity for an experienced Ontario-based underwriter who brings strong technical expertise, local market knowledge, and established broker relationships.

The successful candidate will become an important technical underwriting resource in the Ontario market, working closely with business development leadership to evaluate opportunities, support broker relationships, and help expand the organization’s commercial presence across the province.

This role offers the opportunity to combine hands‑on commercial underwriting with broader market involvement. You will have meaningful autonomy, exposure to a diverse commercial portfolio, and the opportunity to support the continued development of a growing Ontario operation.

Candidates throughout Ontario are encouraged to apply. The role does not need to be based specifically in the Greater Toronto Area.

In this role, you will:

• Assess, price, negotiate, and structure commercial property and casualty risks in accordance with established underwriting guidelines and risk appetite.
• Underwrite a diverse commercial portfolio that may include commercial property and liability, realty, manufacturing, hospitality, construction and course of construction, professional lines, and other commercial exposures.
• Manage both new business and renewal accounts.
• Evaluate opportunities originating through broker and business development relationships within the Ontario market.
• Take ownership of the underwriting process from submission review and risk assessment through quoting, binding, policy documentation, and account finalization.
• Apply strong technical judgment when assessing complex or non-standard commercial risks.
• Build and maintain productive relationships with Ontario brokers and other insurance‑market partners.
• Attend broker meetings, industry events, and market‑development activities as appropriate.
• Work collaboratively with business development and underwriting leadership to evaluate and support new opportunities.
• Provide technical guidance and mentorship to less experienced underwriting professionals.
• Contribute local Ontario market knowledge and insight as the organization continues to expand its presence in the province.
• Manage priorities independently while contributing to a collaborative national underwriting environment.

The Employer

Our client is an established Canadian property and casualty insurer with a growing commercial portfolio and an established history of writing business in Ontario.

The organization offers broad underwriting exposure rather than heavily segmenting individuals by account size, class of business, or new business versus renewals. Senior underwriters are encouraged to take meaningful ownership of accounts and apply professional judgment throughout the underwriting lifecycle.

About You

You are an experienced commercial underwriter who understands both the technical and relationship sides of the Ontario insurance market.

You bring strong commercial property and casualty expertise and are comfortable assessing a broad range of risks independently. You understand the Ontario broker landscape and can evaluate opportunities based on sound underwriting fundamentals and market context.

You are confident working remotely and independently while staying closely connected to underwriting and business‑development colleagues.

You also enjoy sharing your expertise. Less experienced underwriters are comfortable coming to you for guidance, and you are willing to help others strengthen their underwriting judgment, confidence, and technical capability.

Necessary Qualifications Include

• 4+ years of commercial property and casualty underwriting experience, with deeper senior-level experience strongly preferred.
• Demonstrated experience underwriting risks within the Ontario market.
• Strong commercial property and liability underwriting knowledge.
• Knowledge of the Ontario commercial insurance market and broker community.
• Experience underwriting a diverse range of commercial risks.
• Demonstrated ability to independently assess, price, and structure commercial accounts.
• Strong technical judgment and the ability to clearly explain underwriting decisions.
• Experience managing both new business and renewal accounts.
• Strong broker relationship and communication skills.
• Comfort working alongside business‑development professionals and assessing new market opportunities.
• Willingness to participate in broker meetings, industry events, and relationship‑development activities.
• Ability to work effectively and independently in a remote environment.
• Ability and willingness to provide technical guidance and mentorship to less experienced colleagues.
• Willingness to obtain the required insurance licence within the expected timeframe if not already licensed.
• Experience with large realty portfolios, manufacturing, hospitality, construction, builders' risk or course of construction, professional lines, or other specialty commercial risks is considered an asset.
• Experience underwriting business across multiple Canadian jurisdictions is considered an asset.
• Post‑secondary education and/or a Chartered Insurance Professional (CIP) designation is considered an asset.

What's in It for You

• Anticipated base salary of approximately $97,000-$125,000, based on experience, technical expertise, market knowledge, and overall fit.
• Candidates with particularly strong experience whose expectations are modestly above the stated range may still be considered.
• Remote work from Ontario.
• Opportunity to become an important technical underwriting resource within a growing Ontario operation.
• Broad exposure to commercial property and casualty risks.
• Meaningful underwriting autonomy and account ownership.
• Opportunity to help shape the organization’s continued growth in Ontario.
• Strong broker and industry relationship exposure.
• Opportunity to mentor developing underwriting professionals.
• Flexible time off and vacation.
• Group retirement savings plan with employer matching contributions.
• Fitness subsidy.
• Training and professional development assistance.
• Health, dental, and insured benefits.
• Health and lifestyle spending account.
• Employee discount programs.

About Us

DGA Careers has been proudly serving the Canadian insurance industry for over 30 years, specializing in providing insurance recruiting services to major insurers, insurance brokerage firms, and independent adjusting firms. With offices