
AB Claims Representative II – Waterloo, Ontario
Located in Ontario and Nova Scotia, Heartland Mutual Insurance strives to be the Best Mutual. Our team of talented and dedicated professionals challenge the norm and strive to be extraordinary. It’s all about fulfilling our promise with a personal approach. With our team, you’ll bring this purpose to life every day by living our values, being open to change, and pursuing your career aspirations.
Heartland Mutual Insurance has an excellent opportunity in our Claims Department for an AB Claims Representative II.
What you will do…
- Investigate and resolve minor- to medium-complexity Accident Benefits claims.
- Provide excellent customer service through counselling claimants regarding the Statutory Accident Benefits Schedule (SABS), benefit eligibility, and claims process and procedures.
- Correspond with claimants to gather adequate information for confirming priority of payment, WSIB, and/or loss transfer potential.
- Consult for authority requests with respect to payments, settlements, and incurred handling.
- Collaborate with clients, treatment professionals, and employers in the development and ongoing monitoring of case management plans.
- Manage treatment plans and invoicing within Health Claims for Auto Insurance (HCAI).
- Work with our legal counsel where disputes have been filed through the Licence Appeal Tribunal (LAT).
- Ensure medical records and case files are captured and kept up to date within Guidewire.
- Operate within legal, regulatory, and privacy obligations.
What you will bring…
- 3+ years’ experience in handling Accident Benefits claims.
- Post-secondary degree or diploma, or equivalent work experience.
- CIP designation, or willingness to pursue, is an asset.
- Excellent understanding of Accident Benefits insurance coverage.
- Comprehensive knowledge of the SABS, particularly the Minor Injury Guideline (MIG) and factors which affect inclusions or exclusions.
- Working understanding of privacy legislation and the Ontario auto policy, and comprehensive understanding of HCAI.
- Experience working with Guidewire is an asset.
- Experience managing relationships with clients and medical professionals.
What we offer…
In return, we’ll give you countless opportunities to learn and grow. You’ll be empowered to be your best self, do your best work, and make a meaningful impact. Here, you can help shape the future of insurance, win as a team, and grow with us.
At Heartland our benefits are great and include not only health and dental coverage, but also a generous pension plan. All staff members share in our company’s success through our incentive plan. And with our hybrid work model, you get the best of both worlds – the ability to collaborate and connect with great colleagues and to enjoy the benefits of working from home.
Intrigued? We can’t wait to hear from you!
If you have the qualifications we are seeking and would thrive in a work environment where you are valued and respected, please apply on the company website. Accommodations are available on request for candidates taking part in all aspects of the selection process.
A Place Where YOU Can Make a Difference! Proudly Canadian. Mutually Owned.

Located in Ontario and Nova Scotia, Heartland Mutual Insurance strives to be the Best Mutual. Our team of talented and dedicated professionals challenge the norm and strive to be extraordinary. It’s all about fulfilling our promise with a personal approach. With our team, you’ll bring this purpose to life every day by living our values, being open to change, and pursuing your career aspirations.
Heartland Mutual Insurance has an excellent opportunity in our Finance Department for a Financial Analyst.
Financial Analyst – Waterloo, Ontario
What you will do…
- Responsible for monthly journal entries and reconciliation of general ledger accounts.
- Preparation of bank reconciliation and associated journal entries.
- Reconcile Claims Cheques Payable and Retail Sales Tax accounts, oversee reconciliation of Facility Association accounts.
- Prepare accounting entries for investments, reinsurance, personnel costs, Facility Association, and other accounts from source documents.
- Managing broker commissions.
- Preparation of monthly financial analysis for Claims.
- Preparation of interim and year-end external audit schedules, and assistance with annual external audit coordination.
- Supervise and support Finance Co-op Student roles and responsibilities.
- Support preparation of annual budget and forecasting, as well as process improvement.
What you will bring…
- 1-2 years accounting/finance work experience.
- Post secondary accounting/finance degree.
- Working towards CPA designation is an asset.
- Excellent communication, organizational and time management skills.
- Working knowledge of Microsoft Office, with advance proficiency in Excel.
- Experience with Microsoft GP (accounting system) an asset.
What we offer….
In return, we’ll give you countless opportunities to learn and grow. You’ll be empowered to be your best self, do your best work, and make a meaningful impact. Here, you can help shape the future of insurance, win as a team, and grow with us.
At Heartland our benefits are great and include not only health and dental coverage, but also a generous pension plan. All staff members share in our company’s success through our incentive plan. And with our hybrid work model, you get the best of both worlds – the ability to collaborate and connect with great colleagues and to enjoy the benefits of working from home.
Intrigued? We can’t wait to hear from you!
If you have the qualifications we are seeking and would thrive in a work environment where you are valued and respected, please apply on the company website. Accommodations are available on request for candidates taking part in all aspects of the selection process.
A Place Where YOU Can Make a Difference! Proudly Canadian. Mutually Owned.

Senior Field Claims Representative – Waterloo, Ontario
Located in Ontario and Nova Scotia, Heartland Mutual Insurance strives to be the Best Mutual. Our team of talented and dedicated professionals challenge the norm and strive to be extraordinary. It’s all about fulfilling our promise with a personal approach. With our team, you’ll bring this purpose to life every day by living our values, being open to change, and pursuing your career aspirations.
Heartland Mutual Insurance has an excellent opportunity in our Claims Department for a Senior Field Claims Representative.
What you will do…
- Conduct field investigations and provide in-person service for moderate to large loss property claims and liability claims involving spills, crop damage, and property damage.
- Inspect loss locations, gather detailed information through written or recorded statements, and document all findings accurately.
- Collaborate with contractors, engineers, and experts to assess damages and determine repair or rebuild costs.
- Maintain comprehensive documentation in claims files, including investigations, correspondence, and service arrangements.
- Identify and pursue subrogation opportunities, ensuring proper documentation to protect Heartland’s subrogated interests.
- Maintain a proactive diary system to ensure timely follow-up and exceptional service delivery.
- Manage file reserves, process payments accurately, and maintain financial integrity in the policy management system.
- Support the Auto and Casualty teams with field investigations, including site visits, statement collection, and photographic documentation.
What you will bring…
- 10+ years of progressive experience in Property Claims.
- Post-secondary education in a related field or equivalent business experience.
- CIP designation or active progression toward completion.
- Solid knowledge of policy wordings for Commercial, Farm, and Personal Lines property.
- Strong understanding of the Insurance Act, contract law, and civil litigation processes.
- Technical proficiency in loss investigation, damage scoping, documentation, and estimation.
- Proven customer service, communication, and negotiation skills.
- Valid driver’s license with a clean driving record.
- Experience with the appraisal process, ADR, Xactimate software, and CFEI designation are assets.
What we offer…
In return, we’ll give you countless opportunities to learn and grow. You’ll be empowered to be your best self, do your best work, and make a meaningful impact. Here, you can help shape the future of insurance, win as a team, and grow with us.
At Heartland our benefits are great and include not only health and dental coverage, but also a generous pension plan. All staff members share in our company’s success through our incentive plan. And with our hybrid work model, you get the best of both worlds – the ability to collaborate and connect with great colleagues and to enjoy the benefits of working from home.
Intrigued? We can’t wait to hear from you!
If you have the qualifications we are seeking and would thrive in a work environment where you are valued and respected, please apply on the company website. Accommodations are available on request for candidates taking part in all aspects of the selection process.
A Place Where YOU Can Make a Difference! Proudly Canadian. Mutually Owned.

Located in Ontario and Nova Scotia, Heartland Mutual Insurance strives to be the Best Mutual. Our team of talented and dedicated professionals challenge the norm and strive to be extraordinary. It’s all about fulfilling our promise with a personal approach. With our team, you’ll bring this purpose to life every day by living our values, being open to change, and pursuing your career aspirations.
Heartland Mutual Insurance has an excellent opportunity in our Underwriting Department for a Team Lead, Personal Lines Underwriting.
Team Lead, Personal Lines Underwriting – Waterloo, Ontario
As a Team Lead, you will support the Underwriting team with day-to-day functions, including reviewing complex underwriting files, mentoring and coaching individuals, and assigning work to meet required service levels. The Team Lead will be responsible for completing individual performance reviews, which will include development plans catered to each individual. The Team Lead will be innovative and creative, looking for efficiencies in processes and procedures. This position will be essential to our frontline Underwriting staff and ensuring the execution of a high-performing Underwriting team.
What you will do…
- Underwriting portfolio management, creating a high-performance Underwriting culture, improving efficiencies, analysis of new business, and handling complex underwriting referrals.
- Ensure corporate governance, and regulatory compliance policies and procedures are adhered to, and regulatory compliance for day-to-day Underwriting operations is met.
- Guide team members in consistent high-quality Underwriting decisions, and delegate Underwriting authority to ensure effective decision-making.
- Product and pricing management, using market knowledge to help develop products, pricing and services to support our corporate strategy.
- Providing ongoing Underwriting guidance to support team members and reinforcing Heartland’s core Underwriting appetite.
- Collaborate with other departments to maximize portfolio performance.
- Coordinate and provide training and development initiatives.
- Routine audits to identify training gaps.
What you will bring…
- 6+ years of Underwriting experience.
- 1+ years of experience in a leadership role.
- Post-secondary education, with CIP designation as an asset.
- Exemplary analytical skills, both written and verbal, ability to make informed decisions.
- Skilled communication, and can adapt your approach to your audience.
- Ability to influence decisions and negotiate strategically.
- Enthusiasm for learning, and ability to thrive within a team or independently.
What we offer…
In return, we’ll give you countless opportunities to learn and grow. You’ll be empowered to be your best self, do your best work, and make a meaningful impact. Here, you can help shape the future of insurance, win as a team, and grow with us.
At Heartland our benefits are great and include not only health and dental coverage, but also a generous pension plan. All staff members share in our company’s success through our incentive plan.
Intrigued? We can’t wait to hear from you!
If you have the qualifications we are seeking and would thrive in a work environment where you are valued and respected, please apply on the company website. Accommodations are available on request for candidates taking part in all aspects of the selection process.
A Place Where YOU Can Make a Difference! Proudly Canadian. Mutually Owned.

Located in Ontario and Nova Scotia, Heartland Mutual Insurance strives to be the Best Mutual. Our team of talented and dedicated professionals challenge the norm and strive to be extraordinary. It’s all about fulfilling our promise with a personal approach. With our team, you’ll bring this purpose to life every day by living our values, being open to change, and pursuing your career aspirations.
Heartland Mutual Insurance has an excellent opportunity in our Business Development and Marketing Department for a Business Development Advisor.
Business Development Advisor – Waterloo, Ontario
What you will do…
- Manage and develop effective broker relationships at all levels, acting as the first point of contact for our brokers
- Conduct sales planning with brokers to establish a clear understanding of our strategy, growth and profitability tactics.
- Conduct regular broker calls to identify, qualify and convert growth opportunities.
- Routinely evaluate broker performance, collaborate across departments to align on tactics to maintain profitability and achieve strategic objectives.
- Develop a deep knowledge of Heartland’s operations, systems and escalation paths to investigate and resolve broker concerns.
- Use a consultative approach to assist brokers in managing their Heartland portfolio.
- Perform regular reporting on broker insights and market trends.
- Gather intelligence on competitor products, pricing, and compensation.
- Plan, execute and attend company and industry events as professional representative of Heartland.
- Provide effective training and development presentations to brokers in-person and online.
What you will bring…
- University degree or College diploma in a relevant field or CIP/FCIP.
- Minimum 5 Years Insurance Industry experience working in broker-facing roles.
- Minimum of 2 years of underwriting experience preferred
- Exceptional communication skills with the ability to effectively facilitate engaging presentations, meetings and training sessions.
- Strong negotiation skills with the ability to influence others.
- Ability to establish effective business relationships.
- Understanding of broker workflows and technology platforms.
- Strong business management skills and ability to analyze, understand and synthesize quantitative and qualitative data.
- Ability to travel as required.
- Existing network of broker contacts is an asset.
- Understanding of product development, pricing, and implementation is an asset.
- Commercial and/or Farm underwriting experience is an asset.
What we offer…
In return, we’ll give you countless opportunities to learn and grow. You’ll be empowered to be your best self, do your best work, and make a meaningful impact. Here, you can help shape the future of insurance, win as a team, and grow with us.
At Heartland our benefits are great and include not only health and dental coverage, but also a generous pension plan. All staff members share in our company’s success through our incentive plan. And with our hybrid work model, you get the best of both worlds – the ability to collaborate and connect with great colleagues and enjoy the benefits of working from home.
Intrigued? We can’t wait to hear from you!
If you have the qualifications we are seeking and would thrive in a work environment where you are valued and respected, please apply on the company website. Accommodations are available on request for candidates taking part in all aspects of the selection process.
A Place Where YOU Can Make a Difference! Proudly Canadian. Mutually Owned.

Security Analyst – Waterloo, Ontario
Located in Ontario and Nova Scotia, Heartland Mutual Insurance strives to be the Best Mutual. Our team of talented and dedicated professionals challenge the norm and strive to be extraordinary. It’s all about fulfilling our promise with a personal approach. With our team, you’ll bring this purpose to life every day by living our values, being open to change, and pursuing your career aspirations.
Heartland Mutual Insurance has an excellent opportunity in our Information Technology
Department for a Security Analyst.
What you will do…
- Coordinate and conduct network and web application vulnerability assessments.
- Monitor emerging threats, assess risks, and recommend relevant controls and mitigation
strategies. - Provide support for security-related projects and serve as the security consultant to help
guide secure application and infrastructure configurations. - Conduct rigorous oversight of security systems and security configuration administration to
reduce risk to enterprise systems and accounts. - Work with external consultants for independent security audits, penetration testing,
incident response, and risk remediation when necessary. - Manage remediation efforts after security assessment findings outline weaknesses
requiring attention. - Ensure alignment of Heartland security efforts with relevant frameworks, guidelines and
governing bodies. - Ensure operational effectiveness of network security components for enterprise and cloud
environments such as firewalls, VPN and network devices. - Assist in the execution of the delivery of the Cybersecurity roadmap, providing updates on
progress and tracking changes in Heartland’s Cyber risk and security posture. - Promote Cybersecurity awareness throughout the organization, spreading knowledge of
threats, best practices, and effective use of training tools. - Participate in the delivery of cybersecurity and resiliency activities including tabletop
exercises, DR tests, and penetration tests. - Provide guidance and training to other IT staff on cloud security best practices.
What you will bring…
- Post Secondary education in cybersecurity or a combination of education and relevant
experience. - Cybersecurity certifications are assets.
- 1-3 years in relevant Cybersecurity Technology roles.
- Understanding of Network & Security device management.
- Understanding of Cloud security, design, deployment, and management.
- Ability to troubleshoot security events within network and cloud environments.
- Familiarity with IAM tools and practices.
- Good knowledge of Windows platforms, Office 365, and MS Defender.
- Good knowledge of Cybersecurity frameworks, tools, and best practices.
- Effective communication and collaboration abilities.
- Experience in Insurance Technology an asset.
What we offer…
In return, we’ll give you countless opportunities to learn and grow. You’ll be empowered to be your best self, do your best work, and make a meaningful impact. Here, you can help shape the future of insurance, win as a team, and grow with us.
At Heartland our benefits are great and include not only health and dental coverage, but also a generous pension plan. All staff members share in our company’s success through our incentive plan. And with our hybrid work model, you get the best of both worlds – the ability to collaborate and connect with great colleagues and to enjoy the benefits of working from home.
Intrigued? We can’t wait to hear from you!
If you have the qualifications we are seeking and would thrive in a work environment where you are valued and respected, please apply on the company website. Accommodations are available on request for candidates taking part in all aspects of the selection process.
A Place Where YOU Can Make a Difference! Proudly Canadian. Mutually Owned.