Chief of Staff & Strategic Projects Lead
Top Benefits
About the role
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 benefits
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 escalate 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
Relevant Backgrounds 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 Investment banking, consulting, private equity, corporate development or capital markets 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.
Future Barcelona Opportunity 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.
About Talent Advantage
Founded by a group of staffing industry veterans, The Talent Advantage is a team of experienced recruiters who have come together to provide the best possible service to our clients. We use the latest technologies and work holistically to provide a complete recruitment and staffing solution that meets all of our clients’ needs, no matter the field or position that needs to be filled.
We hire our recruitment team based on both their recruiting skills and their previous experience in a range of business specialties, which we match to their assignments. The designations our staff hold give them unique knowledge of what potential employees would best meet your needs. Who better to staff medical positions than a registered nurse? Who knows the minutiae of financial roles like a CPA? Our work doesn’t end once we’ve put forward applicants either. Once you’ve made your selection, we provide ongoing support to both you and the employee to make sure they’re the right fit.
Our headquarters and staff are located in the Greater Toronto Area, so we are intimately familiar with the areas and industries our clients call home. Working in the heart of Canada’s busiest business center, we understand the speed of modern business, and how vital it is to get the best results possible, as quickly as possible.
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Chief of Staff & Strategic Projects Lead
Top Benefits
About the role
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 benefits
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 escalate 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
Relevant Backgrounds 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 Investment banking, consulting, private equity, corporate development or capital markets 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.
Future Barcelona Opportunity 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.
About Talent Advantage
Founded by a group of staffing industry veterans, The Talent Advantage is a team of experienced recruiters who have come together to provide the best possible service to our clients. We use the latest technologies and work holistically to provide a complete recruitment and staffing solution that meets all of our clients’ needs, no matter the field or position that needs to be filled.
We hire our recruitment team based on both their recruiting skills and their previous experience in a range of business specialties, which we match to their assignments. The designations our staff hold give them unique knowledge of what potential employees would best meet your needs. Who better to staff medical positions than a registered nurse? Who knows the minutiae of financial roles like a CPA? Our work doesn’t end once we’ve put forward applicants either. Once you’ve made your selection, we provide ongoing support to both you and the employee to make sure they’re the right fit.
Our headquarters and staff are located in the Greater Toronto Area, so we are intimately familiar with the areas and industries our clients call home. Working in the heart of Canada’s busiest business center, we understand the speed of modern business, and how vital it is to get the best results possible, as quickly as possible.