# Senior Specialist, Benefits at Wealthsimple

Wealthsimple is hiring a Senior Specialist, Benefits. It pays CAD 90k-CAD 112k a year and Level rates it Little AI ●○○○; you can [apply on Wealthsimple](https://jobsbylevel.com/go/e33c4087-97a1-42cb-93ff-e46481f4b73e?utm_medium=ai-agent).

AI Level 1, AI centrality 35 out of 100. Remote (Remote (Canada)).

## Details

- Company: [Wealthsimple](https://jobsbylevel.com/companies/wealthsimple)
- AI level: AI Level 1 (score 35 out of 100)
- Location: Remote (Remote (Canada))
- Salary: CAD 90k-CAD 112k
- Posted: November 6, 2026
- Apply: https://jobsbylevel.com/go/e33c4087-97a1-42cb-93ff-e46481f4b73e?utm_medium=ai-agent
- Free CV review for this job: https://jobsbylevel.com/cv-review?job=senior-specialist-benefits-at-wealthsimple-ac323f

## Description

Build something people love Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $169 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada. We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work . About the team The Total Rewards team, part of People Operations, makes sure the people who build Wealthsimple are well looked after. We design the compensation, benefits, and rewards programs that support our employees across Canada and the US. As the company grows, our offering is getting more flexible to fit the different needs of our people, which means more plans, more providers, and more to get right. We work closely with the business to make sure our programs are practical, easy to use, and actually used. About the role More employees and more flexible benefits mean more questions, more plans, and more data to keep straight. You'll be the person employees turn to when they need help with their benefits, and the one making sure the systems behind those benefits work the way they should. Over time, as AI takes on more of the routine work, this role will lean further into analysis and shaping where our programs go next. What you'll do Own the employee benefits inquiry and escalation queue, from first contact through to resolution, with answers that are timely and human Make sure enrolment and plan data flow correctly between our HRIS and benefits providers, and catch issues before they reach employees Analyse benefits data, utilization, inquiry trends, and cost, to find gaps in our programs Turn what you learn into ideas and recommendations for our plans and future offerings, working with the Benefits Lead and Director, Total Rewards Manage ongoing relationships with our benefits vendors, resolving service issues and ensuring a high-quality experience for our employees Find ways to simplify and automate our benefits processes Improve our self-serve resources so employees can find answers on their own Use AI tools to speed up responses and analysis Skills you bring 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 like utilization, cost, and trends Clear communication, you can explain a complicated benefits question in a way anyone can understand 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 Who you are Organized, you can juggle multiple projects and deadlines without losing track of the details Detail-oriented, because you know a small enrolment error can be a big deal for the person on the other end Discreet and steady when employees bring you sensitive situations A trusted partner to employees, your People Operations teammates, and our benefits providers Curious and quick to try new ideas and tools, including AI, to make the work simpler Comfortable with a role that will evolve, you're excited to spend less time answering the same question and more time improving the programs behind it Why Wealthsimple? 🌸 Top-tier health benefits and life insurance 📈 Long-term group savings with employer match, through Wealthsimple for Business 🌴 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, including Rainbow (2SLGBTQ), Women of WS, and Black at WS 🌎 We are a hybrid team with over 1,500

The description is cut here. Read the full offer: https://jobsbylevel.com/jobs/senior-specialist-benefits-at-wealthsimple-ac323f

Source: https://jobsbylevel.com/jobs/senior-specialist-benefits-at-wealthsimple-ac323f

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