About the teamThe 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 roleMore employees and more flexible benefits mean more questions, more plans, and more data to keep straight. You9ll 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 you9ll 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, you9re 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 employees across North America. The people are one of the best parts of working here: you9ll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.
*Unlimited paid sick days, Wellness Days and the 90 day away program do not apply to certain roles.
ICYMITechnology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we9re always looking for better ways to work - whether that9s new tools, AI, or rethinking how we approach a problem. We don9t expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we9re building.
