Creative Executive Assistant

Operational backbone for a senior creative leader at Wealthsimple. Managing time, commitments, and communications for effective creative function.

Posted 7/27/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 CA$89,600 - CA$112,000 per yearWebsite

Key responsibilities & impact

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.

What you’ll need

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.

Comp & perks

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