Senior Benefits Specialist

Kassen Recruitment; Toronto; On-site; CAD 80,000 - 110,000; Full time

Job summary

A dynamic growth-focused organization in the software sector is seeking a 'Senior Benefits Specialist' to manage and administer employee benefits across 100+ business units effectively. This role offers a chance for cross-border experience and a collaborative environment where your contributions directly impact employee well-being and organizational success. Ideal candidates will have extensive experience with benefits plans in both U.S. and Canada, with strong analytical and customer service skills.

Qualifications

• 5+ years of experience in employee benefits administration in North America (U.S. and Canada).
• Strong knowledge of self-insured benefits plans and regulatory frameworks.

Responsibilities

• Administer U.S. and Canadian employee benefit programs.
• Oversee 401(k), RRSP, and DCPP plan administration.
• Respond to employee inquiries and run benefits reports for compliance.

Skills

Analytical Skills

Customer Service

Communication

Detail-oriented

Problem-solving

Organizational Skills

Education

Post-secondary education in Human Resources, Business Administration or related field

Tools

Excel

Job description

A dynamic and growing organization in the software sector is seeking a Senior Benefits Specialist to join their HR team. This opportunity offers cross-border exposure, complex benefits administration work, and a chance to contribute to a high-impact, employee-centered function. It's ideal for professionals with deep expertise in benefits programs across both the U.S. and Canada, who thrive in fast-paced, detail-oriented environments.

About the Role:

Reporting into a senior HR leader, this position is responsible for managing and administering employee benefits programs across over 100 business units and over 1,000 employees. The role plays a critical part in ensuring accurate and compliant benefits support, with a strong focus on leaves of absence, 401(k)/RRSP plans, and annual enrollment processes.

What You’ll Do:

• Administer U.S. and Canadian employee benefit programs, including health, dental, vision, LTD, AD&D, and employee stock purchase plans
• Support the end-to-end leave of absence processes (e.g., STD, LTD, parental, sick leave) and understand related payroll and compliance implications
• Oversee 401(k), RRSP, and DCPP plan administration, including enrollment, contributions, audits (Form 5500), and coordination with third-party vendors
• Manage annual benefits open enrollment for U.S. plans and support self-insured programs such as STD
• Respond to employee and business unit inquiries with timely, accurate, and customer-centric support
• Run and analyze benefits reports to ensure data accuracy and compliance
• Coordinate with benefits carriers, including Sun Life and Maple, to manage escalations and ensure service excellence
• Contribute to process improvements and special projects related to benefits systems, compliance, and communications

What You Bring:

• Post-secondary education in Human Resources, Business Administration, or a related field
• 5+ years of experience in employee benefits administration in North America (U.S. and Canada)
• Strong knowledge of self-insured benefits plans, regulatory frameworks (e.g., FMLA, ADA, ESA), and pension/retirement savings vehicles
• Advanced Excel skills, including VLOOKUP, XLOOKUP, and Pivot Tables
• Detail-oriented with strong analytical skills and a problem-solving mindset
• Highly organized and capable of managing a large and diverse employee population
• Exceptional customer service and communication abilities
• Experience with Canadian and U.S. benefits carriers and compliance standards is required

Why Join:

This is a great opportunity to work in a collaborative and fast-paced environment where your contributions directly impact employee well-being and organizational success. You’ll join a supportive HR team with the chance to take ownership of meaningful work, gain cross-border experience, and be part of a company that values precision, service, and continuous improvement.