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.

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.

• Manage the day‑to‑day operations of your pod. Conduct side‑by‑side coaching cadences, running coaching and setting 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.

• 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.

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 Advisor Report 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.

• 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).

• 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)

• 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 (2
  
  SLGBTQ), 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.

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