About Oakway Financial Group
Oakway Financial Group is a growing financial services firm specializing in employee benefits, group retirement solutions, life insurance, living benefits, and business insurance planning. We work closely with business owners, professionals, and organizations across Ontario to deliver strategic advice and exceptional service.
We are seeking an experienced Client Service Representative (CSR) to support our Employee Benefits and Insurance divisions. The successful candidate will play an integral role in managing client service activities, supporting advisors, coordinating carrier relationships, and ensuring a seamless client experience across both group and individual insurance products.
This position is best suited for a highly organized, proactive professional who can work independently, manage multiple priorities, and confidently interact with clients, carriers, and internal stakeholders.
Position Summary
The Client Service Representative will be responsible for providing administrative and client service support across:
- Employee Benefits
- Group Retirement Plans
- Life Insurance
- Critical Illness Insurance
- Disability Insurance
- Living Benefits
- Health Spending Accounts (HSAs)
- Business Insurance Support
The successful candidate will act as a key liaison between clients, advisors, and insurance carriers while ensuring all service, renewal, underwriting, and administrative processes are completed accurately and efficiently.
Key Responsibilities
Employee Benefits Administration
- Manage day-to-day service requests for group benefits clients.
- Process employee additions, terminations, salary changes, beneficiary updates, and other plan amendments.
- Liaise with insurance carriers regarding claims, eligibility, billing, and plan administration.
- Prepare renewal documentation and assist with marketing and carrier submissions.
- Coordinate implementation of new employee benefits plans.
- Assist with census reconciliation, plan audits, and data validation.
- Support employee communications and benefits education materials.
- Prepare benefit summaries and client-facing documentation.
Life Insurance & Living Benefits Administration
- Process applications for life insurance, critical illness insurance, and disability insurance.
- Coordinate medical requirements, underwriting documentation, and follow-up activities.
- Monitor pending business and ensure timely completion of outstanding requirements.
- Communicate with clients, advisors, and carriers throughout the underwriting process.
- Assist with policy delivery and placement activities.
- Process ownership changes, beneficiary changes, policy updates, and service requests.
- Maintain accurate records of all in-force policies and pending applications.
Client Service & Relationship Management
- Serve as a primary point of contact for assigned clients.
- Respond promptly and professionally to client inquiries.
- Build and maintain strong relationships with clients and carrier representatives.
- Ensure all service requests are completed accurately and within established timelines.
- Deliver a high level of client satisfaction through proactive communication and service excellence.
Billing, Invoicing & Financial Administration
- Coordinate group benefits billing inquiries and discrepancies.
- Review carrier invoices for accuracy.
- Prepare and manage client invoicing.
- Assist with accounts receivable follow-up and payment tracking.
- Support commission reconciliation and reporting.
- Maintain accurate financial and administrative records.
CRM & Operational Management
- Maintain accurate client records within Zoho CRM and other internal systems.
- Upload, organize, and manage electronic client files and documentation.
- Track renewal dates, policy anniversaries, and service activities.
- Assist with workflow management and process improvement initiatives.
- Support reporting requirements and administrative projects.
- Ensure compliance with internal processes and regulatory requirements.
Qualifications
Required
- Minimum 3 years of experience in:
- Employee Benefits Administration
- Life Insurance Administration
- Insurance Brokerage Operations
- Financial Services Client Support
- Strong working knowledge of:
- Group Benefits
- Life Insurance
- Critical Illness Insurance
- Disability Insurance
- Health Spending Accounts
- Group Retirement Plans
- Experience working directly with insurance carriers and underwriting departments.
- Strong organizational, administrative, and time-management skills.
- Exceptional attention to detail and accuracy.
- Strong written and verbal communication skills.
- Ability to manage multiple priorities in a fast-paced environment.
- Ability to work independently with minimal supervision.
Preferred
- LLQP licensed and in good standing.
- Experience supporting both employee benefits and individual insurance practices.
- Experience using Zoho CRM or similar CRM platforms.
- Advanced proficiency with Microsoft Office Suite (Excel, Word, Outlook, Teams).
- Experience working with carriers including Manulife, Sun Life, Canada Life, Desjardins, Empire Life, RBC Insurance, Beneva, and Blue Cross.
- Experience coordinating client onboarding, renewals, and underwriting workflows.
Core Competencies
- Client Service Excellence
- Attention to Detail
- Relationship Management
- Problem Solving
- Accountability
- Communication
- Organization & Planning
- Time Management
- Team Collaboration
- Professionalism
Compensation & Benefits
- Competitive annual salary of $75,000 – $100,000, based on experience and qualifications.
- Hybrid work environment with one mandatory in-office day every two weeks at our Woodbridge office.
- Comprehensive employee benefits package fully paid by Oakway Financial Group.
- Employer-matched Group RRSP program.
- Paid vacation and personal days.
- Licensing, continuing education, and professional development support.
- Flexible and collaborative work environment.
Ideal Candidate
The ideal candidate is an experienced insurance professional who can confidently support both employee benefits and individual insurance operations. They are highly organized, client-focused, technologically proficient, and capable of managing a diverse range of responsibilities, including service, renewals, underwriting coordination, billing administration, invoicing, CRM management, and carrier relations.
This individual takes ownership of their work, communicates effectively, and consistently delivers a high standard of service to clients and colleagues alike.
How to Apply
Interested candidates are invited to submit their resume and a brief cover letter outlining their relevant experience in employee benefits, life insurance, and client service administration.
- Oakway Financial Group thanks all applicants for their interest. Only those selected for an interview will be contacted.
Pay: $70,000.00-$100,000.00 per year
Benefits:
- Dental care
- Extended health care
- Flexible schedule
- On-site parking
- Paid time off
- RRSP match
Work Location: Hybrid remote in Woodbridge, ON L4H 1X9
