Join the Octagon Insurance Services Team!
A division of SIB Corp.
We are always looking for amazing people to join the team!
Octagon Insurance is seeking an experienced Independent Claims Adjuster to join our growing team. You will manage a diverse portfolio of property, casualty, and automobile claims, with a strong focus on commercial long-haul trucking and cargo losses. We are looking for a self-motivated professional who brings sound judgment, solid investigative and negotiation skills, and a commitment to delivering responsive, professional service throughout the claims process.
Position: Independent Claims Adjuster
Job Type: Remote, Full Time, Permanent
Work Location : Ontario, Canada
Pay: Commission
What You Will Do:
Manage a diverse portfolio of property, casualty, and automobile claims from initial assignment through resolution, with a strong focus on commercial long-haul trucking and cargo claims
Conduct thorough investigations, including interviews, site visits, and reviews of loss reports, supporting documents, and other relevant information
Interpret policy wordings to assess coverage, liability, and damages, and establish appropriate reserves within your authority
Coordinate with appraisers, contractors, legal counsel, and other specialists to assess losses and support timely claim resolution
Negotiate fair and appropriate settlements within your authority and provide recommendations on complex or high exposure claims
Guide insureds through the claims process, clearly explaining coverage, documentation requirements, timelines, and next steps
Maintain accurate claim files, investigation reports, and billing records, including time and expenses
Build and maintain strong relationships with insurers, brokers, insureds, and service providers through responsive, professional service
What You Bring:
A valid Ontario insurance adjuster’s license




Broad claims adjusting experience across property, casualty, and automobile insurance, including personal and commercial lines
Strong experience handling commercial long haul trucking claims, including cargo, physical damage, and third-party losses
A thorough understanding of policy wordings, coverage analysis, liability assessment, and claims settlement practices
Strong investigation, analytical, and negotiation skills, with sound judgment when handling complex or sensitive claims
Excellent communication and relationship-building skills, with the ability to explain complex matters clearly and professionally
The ability to work independently, manage competing priorities, and maintain accurate documentation using claims management systems and Microsoft Office
What We Offer:
One-on-one mentorship and team guidance
Engaging, collaborative work environment
Paid time off, retirement plans, and comprehensive group benefits
Tuition reimbursement and ongoing professional development
About Us:
Octagon Insurance Services is a fully licensed independent insurance adjusting firm providing top quality adjusting services for Insurers, Managing General Agents, Third Party Administrators and Insurance Brokers. We provide all-lines adjusting services across Ontario.
Now backed by SIB Corp. and Brownstone Insurance Managers Inc. (BIM) specializing in commercial property, casualty, automobile, and program insurance.



BIM provides licensed brokers with access to specialized insurance solutions through partnerships with Canadian insurers and the open market. Our continued growth is driven by a dedicated team of experienced professionals and strong relationships with leading insurance carriers across Canada.
*We are an equal opportunity employer that values a diverse workforce of creative minds.
**Please note that the successful candidate must pass a criminal record check upon receiving their employment offer.
***Only successful applicants that the hiring leaders are interested in interviewing will be contacted directly.
Additional Information:
This job advertisement is for a replacement position that has been posted externally.
SIB Corp. o/a StoneRidge Insurance Brokers or any of its affiliate companies may use Artificial Intelligence (AI) enabled or automated tools to assist in the initial screening of applications. These tools help identify qualifications and experience that align with the role requirements.
Please note that AI is used solely to support and never replace our Talent Team. All decisions are made by our Talent Team and hiring leader. No automated tool makes a final decision about one’s candidacy.
Important: No applicant data is shared externally through any AI tools SIB Corp. o/a StoneRidge Insurance Brokers or any of its affiliate companies may use. All information remains securely within our systems and is handled in accordance with privacy and data protection policies.
SIB Corp. o/a StoneRidge Insurance Brokers and all its affiliate companies welcome applications from all qualified individuals and has a procedures in place to provide accommodations for persons with disabilities at all stages of the hiring process and during employment. If you require an accommodation during the interview or hiring process, please contact the Talent Team so that an appropriate accommodation can be arranged.

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