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Team Lead, Investment Representatives

📍 Canada

Finance and Insurance Wealthsimple Inc.

Job Description

Build something people love Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with 3+ million users who trust us with more than $100 billion in assets. And we’re just getting started.

We’re looking for someone who thinks big, sweats the small stuff and keeps things simple. You’ll join a high-bar, fast-paced team where people are trusted to own their work, communicate openly, and ship things that improve our clients’ lives. Collaboration, humility, and an obsession over quality are how we get stuff done.

Be a part of our Canadian success story and help shape the financial future of millions.

Read our Culture Manual and learn more about how we work.

Please note, this role is not eligible for our 90 Days Away Program as per CIRO guidelines.

Required CSI certifications and registrations, no exceptions: Registered with CIRO, CSC, CPH, DFOL, OPSC and IDSC

In this role, you will have the opportunity to:

Be responsible for taking on team escalations and client complaints, analyzing root causes and implementing corrective actions

Be responsible for leading a team of registered agents, provide ongoing feedback and performance reviews, coach and develop Investment Representatives and ensure effective performance management

Work with product teams, trade desk and operations team to modify and enhance product specifications to meet client demand

Identify operational improvements to improve productivity and efficiency

Be responsible for overseeing risk and meeting compliance requirements across all of our trading processes

Grow team expertise to align with business demand and objectives; assess team skills and capabilities and continually look for ways to provide and enhance value delivered

We are looking for people who:

Want to

make a difference . We are a small team effectively reshaping how people look at the industry. We need people who 'get it' and want to play an integral part in helping us accomplish this mission

Have extreme precision and attention to

detail

Are an excellent

communicator

and know how to explain complex concepts and work with a variety of people

Are comfortable digging through

data

to find and analyze desired information

Have great

analytical

and

prioritization

skills. You know how to balance what needs to be done with what’s possible to do. You understand the scope of an issue and its priorityEmbrace technology and the role it plays in financial services

Are a passionate people

leader

that is excited to develop others

Skills we are looking for:

Mandatory CSI certifications: CSC, CPH, DFOL, OSC, OPSC and IDSC

Experience working on a trade desk and with trading platforms

Experience working with clients

Analytical experience with Excel and SQL

Solution focused

Passionate about technology

Why Wealthsimple? Top-tier health benefits and life insurance

Long-term group savings with employer match using our Wealthsimple for Business platform

20 vacation days + 4 wellness days per year, and unlimited sick and mental health days

✈️ 90 days away program: Employees can work outside of Canada for up to 90 days per calendar year

A wide variety of peer and company-led Employee Resources Groups (e.g., Rainbow, Women of Wealthsimple, Black @ WS)

We’re a remote first team with over 1,500 employees across North America - and one of the best things about working here is the people. You’ll be collaborating with incredibly talented, curious, and driven teammates who care deeply about doing great work.

Technology & Innovation at Wealthsimple We believe the future belongs to those who innovate boldly. At Wealthsimple, every team member is expected to lean into new technologies, including AI, and tooling to rethink how we work, solve problems faster, and create even greater value. We're looking for people who are not just comfortable with change but energized by it. Our commitment is to build a company that evolves at the pace of the world around us, and we want you to help lead that future.

DEI Statement At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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Ready to Apply?

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Job Details

Posted Date: February 24, 2026
Job Type: Finance and Insurance
Location: Canada
Company: Wealthsimple Inc.

Ready to Apply?

Don't miss this opportunity! Apply now and join our team.