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Direct Sales Representative – Waterloo/Thamesford, 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 working for a Direct Sales Representative, working out of our Waterloo and/or Thamesford locations.

What you will do…

Sales and Marketing

  • Create new business opportunities using developed networks and build a sales pipeline to meet and exceed quote volume and sales goals.
  • Accurately and fully complete quote and application documents to be presented to clients after conducting front line underwriting and risk selection.
  • Manage renewal process by gathering required information, cross selling, account rounding and presenting renewals as required.
  • Promote the company brand and services/products offered to customers
  • Provide a community presence including participation in company and community events
  • Utilize Heartland’s industry leading technology to truly work mobile and efficiently distribute our insurance product offerings.

Policyholder Service and Relations

  • Provide exceptional service to client queries and recommend coverage solutions
  • Document management with exceptional client file documentation.
  • Process policy changes that are within binding authority and prepare and submit documents for policy changes that are outside authority.
  • Handle finance and claims inquiries for clients as needed.
  • Stay up to date with industry knowledge and actively participate in training initiatives in order to provide exceptional service and provide appropriate coverage solutions to policy holder

What you will bring….

What’s in it for you

Join a Supportive Team: Be part of a collaborative and high-performing team that values knowledge sharing and celebrating wins together.

Comprehensive Total Rewards: Enjoy a competitive compensation package, including health and wellness benefits, pension plan, paid time off, and more.

Career Growth & Development: Take advantage of continuous learning opportunities and stretch assignments.

Make an Impact: Play a key role in helping customers navigate challenging situations with empathy and expertise.

Inclusive Culture: Work in an environment that embraces diversity, equity, inclusion and belonging.

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! 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.

Dedicated to protecting what matters most.

Adjuster Level II, Auto Physical Damage Claims – 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.

We’re looking for a skilled and customer-focused Claims Adjuster II to join our Team!

This role is responsible for managing a wide range of auto damage claims with moderate complexity. This includes both drivable and non-drivable losses, as well as unlisted driver claims where no escalation criteria are triggered. The role requires strong technical knowledge, customer service skills, and the ability to recognize when files must be escalated. The role offers continuous development opportunities with 5–10% of assigned files considered stretch files to support professional growth.

What you will do…

Auto Physical Damage Claims Management:

  • Independently manage drivable and non-drivable auto claims, including collision, comprehensive, theft, and weather-related losses.
  • Investigate, evaluate, and resolve claims with a focus on efficient and fair outcomes.
  • Handle unlisted driver claims within authority, escalating when required per guidelines.
  • Identify and escalate claims involving injury or third-party property damage for appropriate reassignment or consultation.
  • Ensure timely and accurate reserving of all claims in accordance with Heartland’s standards and financial guidelines.
  • Proactively settle total loss claims and issue settlement offers on the same day appraisal approvals are received.

Vendor and Repair Network Coordination:

  • Work collabwith appraisers, who are responsible for developing repair estimates and confirming accurate scoping and pricing with vendors.
  • Coordinate with repair shops to manage and optimize rental vehicle usage.
  • Liaise with rental companies to ensure use of LKQ (Like Kind and Quality) vehicles and control both cost and duration of rental.
  • Manage timely release of vehicles from tow, storage, and salvage providers to reduce cost exposure.

File Documentation and Regulatory Compliance:

  • Maintain detailed file documentation that meets internal quality standards and industry regulations.
  • Ensure proper reserve setting and timely claim settlement in alignment with financial and compliance expectations.

Customer, Broker, and Stakeholder Communication

  • Communicate claim outcomes and next steps clearly and professionally to policyholders, brokers, Agents, and DSC staff.
  • Provide consistent updates and manage expectations through all stages of the claim.

Escalation and Risk Identification:

  • Identify and escalate files with potential fraud, litigation, or off-coverage positions.
  • Collaborate with Senior Adjusters, the QA Specialist, and the Recovery team when file complexity exceeds scope.

CAT Support and Stretch Development:

  • Participate in catastrophe response by triaging and managing claims in surge environments.

What you will bring…

Education and Experience:

  • 2-4 years of auto claims adjusting experience.
  • Post-secondary education in Insurance, Business, or related field; CIP designation in progress preferred.

Technical Skills & Knowledge:

  • Proficient understanding of auto claims processes, vendor collaboration, and cost control measures.
  • Familiarity with claims management systems and digital file documentation tools.

Competencies:

  • Strong decision-making and investigative abilities.
  • Excellent verbal and written communication skills.
  • High attention to detail and organizational skills.
  • Customer-first mindset with professional and empathetic communication.

What’s in it for you…

Join a Supportive Team: Be part of a collaborative, high-performing team that values knowledge sharing, mentorship, and celebrating wins together.

Comprehensive Total Rewards: Enjoy a competitive compensation package, including health and wellness benefits, pension plan, paid time off, and more.

Make an Impact: Play a key role in helping customers navigate challenging situations with empathy and expertise.

Inclusive Culture: Work in an environment that embraces diversity, equity, inclusion, and belonging.

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! 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.

Finance Representative I – 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 Finance Department for a Finance Representative I.

What you will do…

  • Deal directly with both internal and external customers to ensure premiums are received in an efficient and timely manner.
  • Apply payments received via online banking, credit card and cheques.
  • Attend to broker and insured inquires via email and telephone.
  • Process policy changes regarding billing methods.
  • Assist with other Finance tasks as required.

What you will bring…

  • Post-secondary education in Business and/or Accounting is preferred.
  • Successful experience in a customer service environment.
  • Well-organized mindset with an affinity for numbers.
  • Ability to maintain professional standards in a fast-paced environment with shifting priorities.
  • Ability to manage multiple complex tasks.
  • Basic Microsoft Word and Excel skills are essential.
  • Must have a positive attitude.
  • Fluency in English with excellent written, oral and telephone communication skills.

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! 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.

Team Lead, Pricing & Data Analytics – 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 Actuarial department for a Team Lead, Pricing & Data Analytics.

What you will do…

What you will bring…

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! 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.

Actuarial Specialist – 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 Waterloo office for an Actuarial Specialist.

What you will do…

What you will bring…

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! 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.

Manager, IT Platforms and Cybersecurity – 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 strives 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 IT Department for a Manager, IT Platforms and Cybersecurity.

What you will do…

What you will bring….

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. With our in-office work model, you get the ability to collaborate and connect with great colleagues.

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! 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 Adjuster, Property Claims – 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 Adjuster, Property Claims.

What you will do…

What you will bring…

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! 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.

Business Development Advisor – 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 Business Development and Marketing Department for a Business Development Advisor.

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! 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 Corporate Actuarial 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 Finance Department for a Senior Corporate Actuarial Analyst.

What you will do…

  • Assist in preparing quarterly reserve analyses under the guidance of the Appointed Actuary.
  • Support the development and documentation of actuarial liabilities for financial reporting.
  • Contribute to the preparation and peer review of the Appointed Actuary’s Report (AAAR).
  • Support the annual Financial Condition Testing (FCT) process.
  • Perform sensitivity analyses, capital impact assessments, and assist with recommendations for risk mitigation strategies.
  • Collaborate with the Finance team to produce inputs for quarterly/annual financial statements and the organizational budget.
  • Provide reserve estimates, claims projections, and trend analysis to assist in budget planning and forecasting.
  • Design and execute queries using SAS, SQL, etc. to extract and validate large datasets.
  • Develop visuals and reports for internal use, Board reporting, and executive briefings.
  • Assist with the maintenance and enhancement of actuarial models, especially in ResQ.
  • Support the implementation of enhancements to reserving, capital modelling, or profitability analysis frameworks

What you will bring…

  • University degree (Actuarial Science, Mathematics/Statistics or a related discipline). 
  • A minimum of 3 years’ experience in an actuarial/data analysis role, preferably with P&C insurance exposure, or a significant educational background in a related financial services environment.
  • Successful completion of 4 to 6 exams from the Casualty Actuarial Society.
  • High proficiency in SAS, SQL, and Excel is essential.
  • Familiarity and good working knowledge of ResQ. 
  • A good understanding of P&C reserving and capital modelling concepts
  • Demonstrated strength in oral, written and presentation communication skills.
  • Demonstrated teamwork and collaboration in cross-functional projects.
  • Ability to work independently and manage multiple deadlines in a fast-paced environment.
  • Experience with data visualization and reporting tools considered an asset (e.g., Power BI, Tableau).

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! 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.

Direct Sales 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 Direct Sales Department for a Direct Sales Representative.

What you will do…

  • Handle inbound calls and leads for home, auto and small business insurance.
  • Complete risk assessments and manage renewal process.
  • Request referrals from existing clients to help grow the book of business.
  • Promote the company brand and services/products offered to customers.
  • Work within defined limits of authority, consistently providing high quality decisions that support the achievement of Heartland’s financial targets.
  • Manage a renewal portfolio of assigned clients and coordinate the discussion of renewal strategy with underwriting.
  • Review renewals, endorsements, cancellations, and payment notices, ensuring accurate processing of policy documentation.
  • Complete building evaluations using either RCT, Douglas Cost Guide, or CoreLogic.
  • Provide exceptional customer experience through the ongoing development of relationships with key stakeholders.

What you will bring…

  • 2+ years of P&C insurance experience in either a sales or underwriting position.
  • Must have an OTL agent license or the ability to obtain within 60 days of hire (assistance provided).
  • Completion of OSSD. Post-secondary education preferred. 
  • Excellent organization and communication skills. 
  • Completion of CIP, CRM or working towards completion is considered an asset.
  • Familiarity with PowerBroker or other Broker Management Systems is an asset.
  • Familiarity with Guidewire systems 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! 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.