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.
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 Advantages Overview If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us! Hagerty is an automotive enthusiast brand committed to saving driving and to fueling car culture for future generations. We are a leading provider of specialty vehicle insurance, expert car valuation data and insights, live and digital car auction services, immersive events and automotive entertainment custom made for the 67 million Americans who self-describe as car enthusiasts. Hagerty also operates in Canada and the U.K. and is home to Hagerty Drivers Club, a community of over 800,000 who can’t get enough of cars. We are a rapidly growing company that values a winning, values-driven culture. We provide meaningful work for, and invest in, every single team member.

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📌 Unlicensed Operations Specialist (Ontario)
🏢 Hagerty Insurance Agency
📍 Ontario