Job Title: Chief of Staff & Strategic Projects Lead to the Managing Director
Location: North York (Yonge & Sheppard) - Onsite
Employment Type: Full-Time, Permanent
Compensation: Competitive market-based salary $90,000-$115,000 (flexible above this based on experience)
Annual performance bonus: Up to 50% of base (80% average attainment)and comprehensive advantages
The Opportunity A large international organization in the online gaming and entertainment industry is seeking a highly capable Chief of Staff & Strategic Projects Lead to work directly with its Managing Director.
The Managing Director leads international business development, including market entry, government relations, regulatory strategy, licensing and strategic partnerships. At any given time, he may be overseeing 10-15 active initiatives across multiple countries and time zones.
This is not a traditional Chief of Staff position. While the role includes calendar, travel and executive-support responsibilities, its primary focus is owning strategic projects, coordinating regulatory and government-relations campaigns, holding stakeholders accountable and acting as a trusted thinking partner to the Managing Director.
You will attend important meetings, understand the substance behind each initiative and ensure decisions are converted into action. You must be comfortable offering your own perspective, challenging assumptions respectfully and identifying issues or opportunities the Managing Director may not have considered.
Key Responsibilities Own 10-15 concurrent initiatives involving international market entry, licensing, regulatory strategy, government relations and strategic partnerships
Turn broad business objectives into structured project plans with clear stakeholders, deliverables, deadlines and next steps
Maintain a live view of every active project, including its status, blockers, responsible parties and upcoming decisions
Drive projects forward by following up with lawyers, consultants, partners, regulators and internal teams
Identify stalled initiatives, recommend solutions and elevate issues when required
Research political, legal, regulatory and licensing environments in new and existing markets
Help develop strategies for government engagement, regulatory change, licensing and market access
Prepare briefing packages, presentations, position papers, stakeholder maps and executive recommendations
Attend internal and external meetings,



capture decisions and action items, and drive commitments through to completion
Hold structured debriefs with the Managing Director and contribute ideas, observations and alternative approaches
Coordinate with Legal, Regulatory, Finance, Product, Marketing, external counsel, government-relations consultants and commercial partners
Support strategic partnership negotiations, business-development opportunities, and potential M&A; initiatives
Manage the Managing Director's calendar, international travel, priority communications, expenses and weekly planning
Use AI and productivity tools to improve research, meeting capture, drafting, project tracking and overall efficiency
What You Bring At least four years of experience managing complex projects, strategic initiatives or campaigns in a fast-paced environment
Demonstrated ownership of projects from planning and strategy through execution and completion
Experience involving government, public policy, regulatory affairs, licensing, legal matters or another highly regulated industry
Strong project-management skills and the ability to manage numerous slow-moving and competing priorities without losing momentum
Experience preparing executive presentations, briefing materials, research reports or strategic recommendations
Excellent research and analytical skills, including the ability to understand an unfamiliar topic quickly
Strong stakeholder-management skills and the confidence to hold senior internal and external contributors accountable
Excellent written and verbal communication skills
Advanced presentation and spreadsheet capabilities, along with comfort using AI and project-management tools
The confidence and judgment to question an approach, raise concerns and provide a well-reasoned opinion
Exceptional discretion, attention to detail and comfort handling commercially and legally sensitive information
A highly motivated, intellectually curious and ambitious personality




Comfort combining strategic project ownership with hands-on executive support
Ability to work onsite in Toronto and collaborate across international time zones
Potential candidates may come from: Government relations, public affairs, lobbying or political campaign management
Government, legislative, policy or regulatory offices
Law firms, legal project management, senior paralegal or law-clerk positions
Financial services, pharmaceuticals, alcohol, cannabis or other highly regulated industries
International business development, licensing or market-entry roles
Online gaming, technology or digital entertainment companies
A political, legal or online gaming background is not mandatory. The priority is finding someone with strong judgment, project ownership, intellectual curiosity and the confidence to become a genuine strategic partner to the Managing Director.
The Managing Director expects to relocate to Barcelona within approximately three to five years. By then, the successful candidate may be fully trained and able to continue supporting him remotely from Toronto.
Candidates interested in relocating to Barcelona may also have that opportunity, with potential company-supported immigration and relocation assistance. Relocation is preferred but is not required and will not outweigh the importance of experience and personality fit.
Spanish-language ability is an asset but is not required.
Why Join? Work directly with the Managing Director of a large international organization
Gain exposure to global market entry, regulatory strategy, government relations and senior negotiations
Help shape campaigns that may influence laws, regulations and emerging markets
Participate in high-value commercial partnerships and international expansion initiatives
Receive direct mentorship and increasing responsibility
Develop experience across business development, strategic partnerships and M&A;
Pursue substantial long-term career advancement within a global organization
Access a competitive salary, annual performance bonus, comprehensive benefits and professional-development support
Successful completion of a background check and execution of a confidentiality agreement will be conditions of employment.
The organization is an equal-opportunity employer committed to providing an inclusive and accessible recruitment process. Accommodations are available upon request.

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📌 Chief of Staff & Strategic Projects Lead (Ontario)
🏢 Talent Advantage
📍 Ontario