Unlicensed Operations Specialist

hagerty· Hagerty Canada, LLC
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📍 Markham Canada OfficeFull time
Full timeHagerty Canada, LLC

About this role

Say hello to Hagerty 

Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do, and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us!  

As an Unlicensed Operations Specialist, you'll be responsible for fulfilling unlicensed tasks in support of our Underwriting and MSC, Territory Managers, US Unlicensed Flex and Finance teams to achieve key business deliverables.   This position ensures strategic alignment and the optimization of processes to deliver a world class experience to our members, brokers and Business Partners.  This role will require consistent alignment with compliance regulations to ensure processes are accurate and carried out successfully.

What you'll do

Member & Partner Experience (We Bring the HFactor) Overview

  • Process and activate all payment plans
  • Review payment plans and make any necessary adjustments
  • Cancellation overrides and invoice suppressions
  • Enter electronic and cheque payments received from members and brokers
  • Make outgoing phone calls for outstanding and delinquent balances
  • Generate and print member refund, broker commissions and vendor cheques
  • Handle any urgent and miscellaneous items as required 
  • Complete policy cancellation requests and non-licensed policy changes  
  • Call members and brokers for address verification  
  • Request and update all motor vehicle reports
  • Release renewals including necessary changes 
  • Handle any urgent and miscellaneous items as required  
  • Follow up on outstanding application items  
  • Process Hagerty Drivers Club transactions  
  • Greet members and brokers as they enter the building, receive incoming parcel deliveries.   
  • Review outgoing mail batches for approval or decline 
  • Process and package all registered letters 
  • Process all French translations 
  • Open, sort and distribute all incoming mail 
  • Enter Net Promotor Scores, application forms and upload documents for licensed agent review

Team Experience (We drive an authentic culture guided by our core values) Overview

  • Create memorable engagement experiences that embrace culture and inclusivity
  • Consistently demonstrate a growth mindset, remaining open to new learning opportunities
  • Embrace change with an open and positive attitude
  • Exhibits Hagerty Core Values daily

​Operational Excellence (We deliver high quality and consistent results to meet business needs) Overview

  • Collaborate with Finance to optimize best practice and ensure compliance needs are met
  • Liaison between our Member Communications Team and our third-party print vendor 
  • Investigate and resolve any payment related discrepancies
  • Build efficiencies for both US and Canadian procedures, promoting alignment between teams
  • Proven track record of delivering exceptional customer service

Culture of Innovation (We encourage and embrace bold ideas in pursuit of a better way) Overview

  • Actively review processes to build efficiencies
  • Brainstorm and communicate solutions for areas of operational struggle
  • Forward thinking with holistic view of business needs

This might describe you

  • Have a thorough knowledge and understanding of current procedures related to all tasks
  • Build efficiencies for both US and Canadian procedures, promoting alignment between teams
  • Ability to show leadership by supporting team members with questions and procedures
  • Attention to detail with a minimum accuracy of 95% 
  • Proven ability to make decisions for file processing
  • Maintain excellent communication skills and proven customer service abilities
  • Actively participate and have a vested interest in professional development
  • Proficient in utilizing computer systems and applications, particularly MS Office products
  • Operate scanners, production printers and postage machines 
  • Demonstrated capability to multitask effectively in a fast-paced environment
  • Exceptional time management skills
  • Able to manage high workloads while upholding quality standards
  • Strong ability to work independently
  • Adaptable to varying daily operational needs

Key Competencies

  • High Emotional Intelligence  
  • Initiative/Drive  
  • Highly collaborative  
  • Communicates clearly and effectively 

Other things to note

  • This role is In Office – Markham, Ontario
  • Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email recruiting@hagerty.com for compensation, comprehensive benefits and the perks that set us apart.  

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world.

#LI-Onsite 

EEO/AA 

US Benefits Overview

Canada Benefits Overview

UK Benefits Overview

If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

Frequently Asked Questions

Is the salary disclosed for the Unlicensed Operations Specialist position at hagerty?
The salary for this Unlicensed Operations Specialist role at hagerty is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the Unlicensed Operations Specialist position at hagerty located?
This Unlicensed Operations Specialist role at hagerty is based in Markham Canada Office. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the Unlicensed Operations Specialist role at hagerty full-time or part-time?
This is listed as a Full time position. It is posted as a Unlicensed Operations Specialist role in the Hagerty Canada, LLC department at hagerty.
Which team or department does the Unlicensed Operations Specialist at hagerty belong to?
This Unlicensed Operations Specialist position is part of the Hagerty Canada, LLC department at hagerty. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Unlicensed Operations Specialist position at hagerty?
Click the "Apply Now" button on this page. You will be redirected to hagerty's official application portal hosted on workday where you can submit your application directly.
When was the Unlicensed Operations Specialist job at hagerty posted?
This Unlicensed Operations Specialist position at hagerty was posted on Aug 14, 2026. Apply as soon as possible — early applications are often reviewed first.
Unlicensed Operations Specialist
hagerty
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