Senior Benefits Specialist

Kassen Recruitment; Toronto; On-site; CAD 75,000 - 100,000; Full time

Job summary

A dynamic organization in the software sector seeks a Senior Benefits Specialist to enhance their HR team. This role focuses on managing employee benefits programs across multiple business units, ensuring compliance, and providing exceptional support. Ideal candidates are experienced in cross-border benefits administration and thrive in fast-paced environments.

Qualifications

• 5+ years of experience in employee benefits administration in North America.
• Strong knowledge of self-insured benefits plans and regulatory frameworks.
• Experience with Canadian and U.S. benefits carriers and compliance standards.

Responsibilities

• Administer U.S. and Canadian employee benefit programs.
• Oversee 401(k) and RRSP plan administration.
• Manage annual benefits open enrollment and respond to inquiries.

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

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.