Creative Executive Assistant, Wealthsimple
CA$89.6-112k
Offers Equity
Professional investing services made simple
Job no longer available
Professional investing services made simple
1001+ employees
Job no longer available
CA$89.6-112k
Offers Equity
1001+ employees
Company mission
To help everyone achieve financial freedom.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
- 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
Our take
Wealthsimple is one of a crop of robo-advisors trying to democratise investment management. These companies are disrupting the industry by automating many of the processes involved in investment, removing the need for human advisors.
But while other so-called robo-advisors are focused on courting the high end of the market, Wealthsimple is trying to provide the same types of tools and advice to all users, regardless of the amount they have to invest.
Wealthsimple does have higher fees than some other robo-advisors such as Betterment and Charles Schwab. However, the company believes that it provides a more user-friendly platform, tailored to millennials who will be attracted to Wealthsimple due to its ease of use and social impact offerings.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-10% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
Oct 2025
$392.7m
LATE VC
May 2021
$535.4m
LATE VC
Total funding: $1.2bn
Company benefits
- Retirement savings matching plan through Wealthsimple Work
- Company equity for full-time employees
- Access to Premium Client perks, including personal finance learning & advice and a boosted interest rate on deposits
- Paid parental leave (6 months topped up to 100% of salary)
- 20 vacation days per year
- 90 Days Away program
- Top-tier health benefits
- Life & disability insurance
- Generous sick and mental health days
- Employee resource plan including services like RMT, psychology, and physiotherapy
- Up to $5,000 per year for mental health supports
- Gender Affirmation benefits
- Up to $1,500 per year for professional development
- Up to $1,500 per year for wellness and home office expenses
- Employee resource groups
- Social impact hours
Company HQ
Fashion District, Toronto, ON
Leadership
Michael Katchen
(Co-Founder & CEO)Previously worked as a Business Analyst at McKinsey and then at Ancestry.com as Country Director for Canada.
Share this job
View 22 more jobs at Wealthsimple