Executive Assistant

Wealthsimple's mission is to help everyone achieve financial freedom – by making financial services simple, transparent, and low-cost. We're Canada's largest fintech, trusted by over 3 million clients with more than $100 billion in assets. We move fast, we own our work, and we care deeply about the people using our products. If that sounds like you, keep reading.

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 will support a group of 3-4 VPs across our R&D (Product) organization. This role requires strong judgment, operational rigor, and the ability to operate as a force multiplier for senior leaders. You will own executive operations end-to-end, ensuring VPs are focused on the highest-value work while driving efficiency across teams.

• Own high-volume calendars for 3–4 VPs, making trade-offs to balance focus time and stakeholder engagement

• Act as a gatekeeper and strategic partner to VPs, challenging low-value meetings and ensuring alignment with top priorities

• Lead end-to-end execution of internal events (takeovers, go-days, all-hands): owning logistics, timelines, stakeholder alignment, and execution

• Manage cross-time zone coordination for international teams with minimal friction and no scheduling inefficiencies

• Own expense management and financial approvals with accuracy, speed, and accountability

• Coordinate travel, anticipating changes and minimizing executive downtime

• Partner seamlessly with other R&D EAs to ensure consistent coverage and alignment

• Maintain absolute discretion with sensitive information

• Identify inefficiencies and implement scalable processes that materially improve executive leverage and team effectiveness

• 4 to 7 years supporting multiple leaders (VP+) from Product/Engineering environments

• Strong calendar ownership and prioritization; able to make trade-offs and push back when needed

• Comfortable coordinating across multiple time zones (NAM) and distributed teams

• Proven experience managing mid-size internal on/off-site events end-to-end

• Highly organized, detail-oriented, and a clear communicator with strong stakeholder judgment

• Proactive and autonomous; identifies issues and solves them without direction

• Discreet and reliable with sensitive information

• Experience with AI tools (Gemini, Claude) to improve efficiency and automate workflows

• Proficient with Google Workspace, Slack, Notion, and Figma

🌸 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.

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.