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.
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About the Role
We are seeking a strategic Legal Counsel to support on high-impact internal investigations, litigation and disputes, and help manage legal aspects of regulatory, compliance, and operational incidents across the enterprise. The successful candidate will bring deep experience in litigation, financial services regulation, regulatory enforcement, internal investigations, and crisis response.
About the team
This role sits within Wealthsimple's Regulatory function, reporting to the Director, Legal (Risk & Enterprise). We handle the moments where things go wrong or get contested — investigations, incidents, and disputes — and help the business work through them with judgment and rigour. As Wealthsimple grows, so does the volume and complexity of this work, and this team is being built to meet that head-on: not just responding to individual matters, but building the frameworks and processes that let us handle them consistently and well.
What You’ll Do:
Lead complex investigations involving regulatory and supervisory matters, fraud, whistleblower complaints, sales practices and customer harm - from investigation strategy through witness interviews and forensic document review.
Support the legal response to operational and compliance incidents, including cybersecurity, market conduct, consumer protection, and fraud.
Support our enterprise crisis management, incident and escalation frameworks.
Partner with Compliance, Risk, Privacy, Finance, and Information Security to identify risks and recommend enhancements.
Manage litigation proceedings and pre-litigation disputes or complaints including the management of external counsel.
Provide legal advice and guidance on a range of legal and strategic issues impacting the business and develop tailored solutions to complex problems.
Skills you bring
LL.B. or J.D. and member of a Canadian provincial bar association with an active membership.
5 to 7 years of litigation experience, preferably with a mix of private practice and in-house experience.
Demonstrated knowledge in areas related to litigation, internal investigations, and/or crisis response in a regulated industry, with a preference for experience advising financial institutions, technology, or Fintech companies.
Nice to Have
Bilingualism (English and French).
Admission to the New York bar.
Who you are
You exercise sound judgment and discretion, especially when the stakes and ambiguity are high
You stay composed under pressure — incidents and crises don't rattle you, they focus you
You're comfortable advising senior leaders directly, and you know how to make a complex legal issue clear and actionable
You take ownership end-to-end, from strategy through execution, and you build process along the way rather than leaving it to someone else
You build trust easily — with internal partners, with regulators, and with outside counsel
You can hold several high-stakes matters at once without losing precision on any of them
🌸 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.
ICYMITechnology & 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.
