Creative Executive Assistant

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Wealthsimple

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

Founded 2014

💼 Consulting

🛡️ Insurance

💳 Fintech

🔥 Funding within the last year

💰 $393M Series E - Wealthsimple on 2025-10

Consulting • Insurance • Fintech

Wealthsimple is a Canadian financial technology company that provides consumer banking, investing, and wealth management services. It offers chequing accounts, savings, credit cards, self-directed trading (stocks, ETFs, options), cryptocurrency trading, managed portfolios, tax services, and advisory wealth management for high-net-worth clients. Wealthsimple combines digital-first banking and low-fee investing products aimed at retail customers, along with tools and educational content to support personal finance.

📋 Description

• Own the calendar. Not just book meetings. Proactively manage time so the right things get attention and the noise gets filtered out. • Stay ahead of commitments. Proactively track what's coming, what's overdue, and what needs to move. Build the rituals to keep work moving. • Be available when it counts. This leader works weekends (our TLDR newsletter ships Monday and good ideas don't wait). You'll need to match that cadence when it matters. • Run meeting operations. Agendas, notes, follow-ups, and accountability. Cascade clarity to the creative team. • Communicate on behalf of. Draft messages, prep briefs, and manage correspondence with the judgment to know what needs escalation and what doesn't. • Handle the operational layer. Expenses, invoices, travel, documents. • Connect the dots across the org. Build relationships with the people around this leader: their direct reports, cross-functional partners, and leadership, so you always have context on what's important.

🎯 Requirements

• 5-7 years supporting a senior leader, ideally in a creative, brand, or editorial environment. Bonus points if you've worked in an agency or high-growth company. You know what it means to move fast and keep up. • Genuine organizational instinct. You don't wait to be asked. You anticipate. • Confidence without ego. You'll push back on low-priority requests and protect the leader's time, even when it's uncomfortable. • High emotional intelligence. You know this executive's working style and you are able to adapt. • Strong communicator. You can write a tight Slack message or prep a clear brief, and you know when to pick up the phone instead. You don't shy away from pushing for clarity. • Comfort with ambiguity. Priorities shift. Plans change at the last minute. You recalibrate, stay calm and move work forward. • Proficiency in Google Workspace and Slack. Figma familiarity is a bonus. • AI fluency. Wealthsimple is an AI-native organization. You're already using AI tools to work faster and smarter, and you're comfortable driving adoption with the people around you.

🏖️ Benefits

• 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 • Collaboration with incredibly talented, curious, and driven teammates