Job Title: Executive Assistant
Location: North York, ON (Yonge & Sheppard)
Future Relocation: Europe (within 3–5 years)
Salary: $90,000–$115,000 + Annual Salary Review
Bonus: Up to 50% Annual Performance Bonus (Average attainment of 80% of maximum)
Total Compensation: $120,000-$165,000
About the Opportunity
Join a globally recognized technology company operating at the forefront of digital entertainment and international market expansion.
With operations spanning multiple continents and a rapidly growing global footprint, the organization is continuously entering new markets, navigating complex regulatory environments, negotiating strategic partnerships, and executing high-impact commercial initiatives.
This is an exceptional opportunity for an ambitious, highly organized professional who wants unmatched exposure to executive leadership, international business development, licensing strategy, and corporate growth.
The Role
This is far more than a traditional Executive Assistant position.
You will serve as the Managing Director's strategic right hand—part Executive Assistant, part Chief of Staff, part project manager.
You'll participate in executive meetings, coordinate major international initiatives, track strategic priorities, and ensure nothing falls through the cracks.
You'll gain exposure to:
- International market expansion
- Commercial negotiations
- Regulatory and licensing strategy
- Government and stakeholder engagement
- Executive decision-making
- Cross-functional leadership
This is a rare opportunity to work alongside a senior executive responsible for launching operations across multiple countries simultaneously.
The successful candidate will relocate with the Managing Director to Europe within approximately 3–5 years. This is intended to be a long-term partnership rather than a short-term administrative role.
Key Responsibilities
Executive Support
- Manage the Managing Director's calendar strategically, ensuring priorities remain aligned with long-term business objectives.
- Prioritize incoming communications and requests.
- Coordinate complex international travel including flights, accommodations, visas, itineraries, and last-minute changes across multiple time zones.
- Manage expense reports, approvals, and executive administrative processes.
- Assist with select personal and family logistics that enable executive productivity.
Meetings & Executive Accountability
- Attend executive meetings and prepare briefing materials in advance.
- Document key decisions, action items, and follow-up responsibilities.
- Ensure action items are completed across internal teams.
- Conduct structured post-meeting debriefs and identify missed opportunities or required follow-up.
- Facilitate weekly planning sessions to prioritize strategic initiatives.
- Help keep executive priorities focused and commitments on track.
Strategic Project Management
- Maintain oversight of numerous concurrent international projects.
- Track milestones, owners, dependencies, risks, and timelines.
- Monitor slow-moving initiatives and proactively identify blockers.
- Prepare executive project status reports and leadership updates.
Research & Business Intelligence
- Conduct market, regulatory, competitive, and commercial research.
- Perform background research on potential partners and stakeholders.
- Prepare executive briefing notes before meetings.
- Monitor industry developments and emerging opportunities.
Executive Deliverables
- Build executive presentations and briefing materials.
- Prepare market analyses, spreadsheets, business models, licensing comparisons, and project trackers.
- Draft executive correspondence, reports, summaries, and strategic documents.
Regulatory & Legal Coordination
- Coordinate with internal legal, compliance, and external advisors.
- Track application deadlines, regulatory submissions, and licensing requirements.
- Monitor document requests and ensure timely completion
Cross-Functional Liaison
Work closely with:
- Executive leadership
- Legal & Compliance
- Finance
- Marketing
- Technology teams
- External legal counsel
- Government agencies
- Commercial partners
- Industry associations
Process Improvement & AI Enablement
- Continuously improve executive workflows using AI and productivity tools.
- Develop efficient systems for research, meeting documentation, drafting, and project tracking.
- Identify opportunities to automate repetitive administrative processes.
Qualifications
- 4+ years supporting senior executives, founders, partners, or C-suite leaders in a fast-paced environment.
- Outstanding organizational skills with the ability to manage numerous long-term initiatives simultaneously.
- Excellent research, analytical, and problem-solving abilities.
- Advanced PowerPoint, Excel, and presentation development skills.
- Strong proficiency with modern AI productivity tools.
- Exceptional written and verbal communication skills.
- High attention to detail.
- Ability to thrive in ambiguous, fast-changing environments.
- Strong judgment and confidence to challenge priorities when necessary.
- High level of professionalism, integrity, and discretion.
- Ability to work independently while managing multiple competing priorities.
- Flexibility to support a global organization operating across multiple time zones.
- Willingness and ability to relocate to Europe within 3–5 years.
- Successful completion of background screening and confidentiality requirements.
Highly Valued Backgrounds
Experience in one or more of the following environments is considered a significant asset:
- Government relations
- Public affairs
- Regulatory affairs
- Political offices
- Investment banking
- Private equity
- Capital markets
- Corporate law firms
- Financial services
- Pharmaceutical
- Cannabis
- Alcohol & beverage
- High-growth technology companies
- International business development
- Global operations
- Live events
- Luxury brands
- Fashion
- High-volume logistics
Additional assets include:
- Experience supporting executives across multiple countries and time zones.
- Spanish language skills or willingness to become professionally proficient (language training provided).
- Previous experience supporting both executive business responsibilities and occasional personal matters.
Total Rewards
- Competitive base salary with annual compensation reviews.
- Annual performance bonus of up to 50%.
- Direct mentorship from a globally recognized executive leading international expansion initiatives.
- Significant exposure to executive leadership, international business strategy, regulatory affairs, and commercial negotiations.
- Company-supported relocation to Europe, including immigration and relocation assistance.
- Language training support.
- Comprehensive health and wellness benefits.
- Paid vacation and sick leave.
- Transportation assistance.
- Employee wellness initiatives.
- Team events and additional employee perks.
This organization is committed to fostering an inclusive, diverse, and respectful workplace. Accommodation is available throughout the recruitment process for applicants requiring accessibility support.