Creative Executive Assistant

Portage Ventures GP Inc.; United States; Hybrid; USD 90,000 - 140,000; Full time

Benefits offered by this job

Health benefits

Employer 401k match

Paid vacation and wellness days

Job summary

Wealthsimple is seeking an organized and proactive executive assistant to support one of its most senior creative leaders. You will manage calendars, coordinate cross‑functional work, and ensure that critical initiatives stay on track in a fast-paced, AI‑driven environment.

You’ll thrive on keeping priorities clear, protecting the leader’s time, and delivering crisp briefs and updates. This is a hybrid North American role with strong collaboration across product, marketing, and design teams.

Qualifications

• 5–7 years supporting a senior leader in creative, brand, or editorial environments.
• Genuine organizational instinct and proactive mindset.
• Confidence with no ego; able to push back on low-priority requests.
• High emotional intelligence and adaptability.
• Strong written and verbal communication; concise briefs.
• Comfort with ambiguity; ability to recalibrate quickly.
• Proficiency with Google Workspace and Slack; Figma familiarity is a bonus.
• AI fluency and willingness to drive adoption.

Responsibilities

• Own the calendar; proactively manage time so the right things get attention.
• Stay ahead of commitments; track what's coming and what needs to move.
• Be available when it counts; align with weekend cadence for the TLDR newsletter.
• Run meeting operations: agendas, notes, follow-ups, accountability.
• Draft messages and briefs; manage correspondence with escalation awareness.
• Handle the operational layer: expenses, invoices, travel, documents.
• Connect the dots across the organization; maintain context with leaders and cross-functional partners.

Skills

Executive support

Organizational instinct

Proactive prioritization

Emotional intelligence

Clear communication

Ambiguity tolerance

Google Workspace

Slack

Figma

AI fluency

Tools

Google Workspace

Slack

Figma

Job description

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 $155 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.

About the Role

Wealthsimple's Chief Content Officer leads one of the most visible and fast-moving functions in the company: brand, editorial, and creative. This role exists to make sure that work actually happens.

You’ll be the operational backbone for a senior creative leader: managing their time, protecting their focus, staying two steps ahead, and making sure nothing falls through the cracks. This isn't a task-taking role. It's a thinking-and-doing role for someone who wants real proximity to how a high-output creative function runs.

If you're energized by being the most organized person in the room, can hold priorities without being asked twice, and know when to push and when to protect: this is your role.

What You'll Do

• 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 Bring

• 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.

Why This Role

You’ll work directly alongside one of Wealthsimple's most senior creative leaders during a period of real growth. The exposure is significant. If you want to understand how brand, editorial, and creative strategy works at scale, and you want to be in the room where it happens: this is the role.

Why Wealthsimple?

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.

ICYMI

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.