Executive Assistant
WFA Digital Insight
As remote work continues to shape the future of employment, the demand for skilled executive assistants has grown significantly. With the rise of fintech, companies like Wealthsimple are leading the way in innovative financial services. According to recent statistics, the fintech industry has seen a 25% increase in job openings over the past year. To succeed in this role, candidates will need to possess strong digital skills, excellent communication abilities, and a deep understanding of remote work dynamics. Wealthsimple's commitment to diversity and inclusion makes this an attractive opportunity for those who value a progressive work environment. Before applying, candidates should be prepared to showcase their ability to work autonomously, think critically, and drive efficiency in a fast-paced setting.
Job Description
About the Role
The Executive Assistant role at Wealthsimple is a unique opportunity to support a group of 3 VPs across the R&D organization. As a key member of the team, you will be responsible for owning executive operations end-to-end, ensuring VPs are focused on high-value work while driving efficiency across teams. This role requires strong judgment, operational rigor, and the ability to operate as a force multiplier for senior leaders.The R&D organization at Wealthsimple is a dynamic and fast-paced environment, with a strong focus on innovation and collaboration. As an Executive Assistant, you will be working closely with the VPs to ensure seamless execution of internal events, manage cross-time zone coordination, and own expense management and financial approvals.
Wealthsimple is committed to creating a work environment that is inclusive, diverse, and empowering. As an Executive Assistant, you will be an integral part of this effort, working closely with the VPs to drive initiatives that promote diversity, equity, and inclusion.
What You Will Do
- Own high-volume calendars for 3 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, including 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
What We Are Looking For
- 4 to 7 years of experience supporting multiple leaders (VP+) from Engineering environments
- Understanding of Engineering priorities and structures
- 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
Nice to Have
- Experience working in a fintech or tech industry
- Knowledge of financial services and products
- Certification in executive assistance or a related field
- Fluency in multiple languages
Benefits and 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
- Opportunity to work outside Canada for up to 90 days per year
- Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS
- Access to cutting-edge technology and tools
- Professional development opportunities
- Flexible work arrangements and remote work options
How to Stand Out
- To stand out in your application, be sure to highlight your experience with digital tools and platforms, as well as your ability to work autonomously and think critically.
- When preparing for an interview, research Wealthsimple's products and services, and be ready to discuss your understanding of the fintech industry.
- Showcase your attention to detail and organizational skills by providing specific examples from your previous experience.
- If you have experience working in a remote or distributed team, be sure to highlight this in your application and during the interview process.
- Don't be afraid to ask questions about the company culture and values, and how they impact the role and responsibilities of the Executive Assistant.
- Be prepared to discuss your experience with AI tools and how you have used them to improve efficiency and automate workflows.
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