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From the employer's careers site First seen 9 Nov 2026

Senior Specialist, Benefits

Wealthsimple Remote (Canada) Remote senior full-time

Salary

CA$89.6K - CA$112K per year

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Description

Wealthsimple is looking for a Senior Specialist, Benefits to join the Total Rewards team. The successful candidate will be responsible for owning the employee benefits inquiry and escalation queue, ensuring accurate enrolment and plan data, analyzing benefits data, and turning insights into recommendations for future offerings.

Key Responsibilities:

  • Provide timely and human support to employees with benefits inquiries and escalations
  • Ensure seamless data flow between HRIS and benefits providers
  • Analyze benefits data to identify gaps and opportunities for improvement
  • Collaborate with the Benefits Lead and Director, Total Rewards to develop new ideas and recommendations
  • Manage relationships with benefits vendors and resolve service issues
  • Simplify and automate benefits processes where possible
  • Improve self-serve resources for employees
  • Leverage AI tools to enhance responses and analysis

Requirements:

  • 3-5 years of experience in benefits administration or management, covering both Canadian and US programs
  • Strong analytical skills and comfort working with benefits data
  • Excellent communication and interpersonal skills
  • Experience handling employee escalations and exceptions with sound judgment and discretion
  • Experience with vendor management

Nice to Have:

  • Experience administering benefits in Workday
  • Exposure to benefits program design

What We Offer:

  • Competitive salary: CA$89.6K - CA$112K
  • Top-tier health benefits and life insurance
  • Long-term group savings with employer match
  • 20 vacation days, 4 wellness days, and unlimited sick and mental health days per year
  • 90 days away: work outside Canada for up to 90 days per year
  • Employee resource groups and a hybrid team environment

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Skills

Required

Nice to have

Ready to apply?

You apply with the employer directly. Their original posting is here: https://jobs.ashbyhq.com/wealthsimple/9c9cab09-b275-4a5c-b4b0-bb397a15fcc4

Apply on Wealthsimple