Senior Specialist, Benefits

Job not on LinkedIn

🔥 16 minutes ago

🇨🇦 Canada – Remote

💵 CA$89.6k - CA$112k / year

⏰ Full Time

🟠 Senior

👩‍👩‍👧‍👦 Human Resources (HR)

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Wealthsimple

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

Founded 2014

💼 Consulting

🛡️ Insurance

💳 Fintech

💰 $393M Series E - Wealthsimple on 2025-10

Consulting • Insurance • Fintech

Wealthsimple is a Canadian financial technology company that provides consumer banking, investing, and wealth management services. It offers chequing accounts, savings, credit cards, self-directed trading (stocks, ETFs, options), cryptocurrency trading, managed portfolios, tax services, and advisory wealth management for high-net-worth clients. Wealthsimple combines digital-first banking and low-fee investing products aimed at retail customers, along with tools and educational content to support personal finance.

📋 Description

• Own the employee benefits inquiry and escalation queue from first contact through resolution • Ensure enrolment and plan data flow correctly between the HRIS and benefits providers • Identify issues before they affect employees • Analyse benefits data, utilization, inquiry trends, and cost to identify program gaps • Develop ideas and recommendations for benefits plans and future offerings with the Benefits Lead and Director, Total Rewards • Manage ongoing relationships with benefits vendors • Resolve vendor service issues and ensure a high-quality employee experience • Simplify and automate benefits processes • Improve self-serve resources for employees • Use AI tools to accelerate responses and analysis

🎯 Requirements

• 3–5 years of experience in benefits administration or management • Experience covering both Canadian and US benefits programs • Strong analytical skills and comfort working with benefits data such as utilization, cost, and trends • Clear communication skills and ability to explain complex benefits questions clearly • Experience handling employee escalations and exceptions with sound judgment and discretion • Experience with vendor management • Organized and able to manage multiple projects and deadlines • Detail-oriented • Discreet and steady when handling sensitive employee situations • Curious and willing to try new ideas and tools, including AI • Comfortable with an evolving role • Legally eligible to work in Canada • Nice to have: experience administering benefits in Workday • Nice to have: exposure to benefits program design

🏖️ Benefits

• Top-tier health benefits and life insurance • Long-term group savings with employer match, through Wealthsimple for Business • 20 vacation days per year • 4 wellness days per year • Unlimited sick and mental health days per year (not applicable to certain roles) • Work outside Canada for up to 90 days per year through the 90 days away program (not applicable to certain roles) • Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS • Equity compensation for permanent employees • Flexible benefits programs • AI tools supporting parts of the hiring process

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