Senior Specialist, Benefits

BUILD SOMETHING PEOPLE LOVE

The company 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. The company 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 [link for members] and learn more about how we work [link for members]

ABOUT THE TEAM

The Total Rewards team, part of People Operations, makes sure the people who build the company 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 the company?

🌸 Top-tier health benefits and life insurance

📈 Long-term group savings with employer match, through the company 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: you'll 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.

ICYMI

Technology & Innovation at the company: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.

Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.