Team Lead, Investments Representative

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 $125 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.

We’re looking for a Team Lead to join our Investment Representatives team, you’ll oversee a pod of Investment Representatives and Senior Investment Representatives. This is a highly hands-on, player-coach role. You’ll be in the queue alongside your team, setting the pace, conducting real-time coaching, managing trade reviews, and ensuring flawless compliance standards on every interaction.

What you’ll do

• Manage the day-to-day operations of your pod. Conduct side-by-sides, run coaching cadences, and set the standard by getting into the queue yourself.

• Own your team's output goals, CSAT, trade execution accuracy, and compliance adherence. Conduct regular trade reviews and quality assurance checks for manual trades (equities, options, crypto).

• Jump into high-pressure, time-sensitive client situations—trading outages, margin events, or corporate actions, partnering with Compliance, Risk, and the Trade Desk to drive resolution.

• Support our internal certification pipeline. Mentor aspiring reps, assess their readiness, and help them master complex wealth management and trading concepts.

• You don't just operate in a silo. You have a proven track record of partnering directly with Trading, Compliance, or Product leadership to design, build, and roll out net-new processes that directly improve the client experience while maintaining strict regulatory standards.

What you bring

• Demonstrated leadership or mentorship experience in a regulated financial environment (e.g., formal Team Lead, Senior Representative).

• Deep knowledge of wealth management, trading strategies, options, margin accounts, and cryptocurrency, and the ability to explain them simply.

• You sweat the details. You can spot a missed step or compliance gap instantly and address it constructively in the moment.

Required Licenses & Designations

📌 Note for Applicants: All reported regulatory credentials, active approvals, and exam completions will be subject to primary-source verification via the National Registration Database (NRD) and CIRO AdvisorReport records. Misrepresentation of regulatory status will lead to immediate and permanent disqualification from consideration for this and future roles, and may be escalated to regulatory authorities.

Option A: Legacy Pathway (Pre-January 1, 2026)

Candidates who were licensed under the previous Canadian Securities Institute (CSI) framework must carry active, verified registrations on the National Registration Database (NRD):

• Mandatory Active Registration Status: Registered with CIRO as an Investment Representative (IR) AND a Supervisor.

• Mandatory Product Licensing: Must hold active approval for Securities/Equities AND Options.

• Active approval for Futures (candidates without Futures licensing will be expected to complete this requirement post-hire).

Option B: New CIRO Exam Pathway (January 1, 2026, Onward)

Candidates qualifying under the updated assessment-centric CIRO proficiency model must have successfully completed the following official CIRO examinations:

• Canadian Investment Regulatory Exam (CIRE) (Replaces legacy CSC/CPH requirements)

• CIRO Derivatives Exam (Replaces legacy DFOL requirements)

• CIRO Supervisor Exam (Replaces legacy OPSC/BMC requirements)

--

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: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.

ICYMI

Technology & Innovation at Wealthsimple: 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.