Manager, Recent Markets – Chief of Staff to the Managing Director Location: North York (Yonge & Sheppard), Mon–Fri, 8am–5pm (onsite)
Salary $105,000–$135,000 (flexible above based on experience)
Bonus Up to 50%/year (Total comp: $155,000–$200,000+)
The Company One of the world's largest online poker networks, headquartered in Toronto with offices in 9 global cities and 700+ employees. Holds the largest online poker market share globally, a Guinness World Record for largest online poker prize pool, and counts a World Poker Champion among its ambassadors.
The Role The Managing Director leads global business development — market entry, licensing, regulatory strategy, lobbying, and partnerships — running 10–15 live market-entry projects across jurisdictions and time zones simultaneously. This role is the person who makes all of it move: not an EA role, but a genuine thinking partner and portfolio owner who sits beside him in negotiations, regulator meetings, and senior strategy discussions.
The MD sets strategy and owns commercial decisions; this hire owns project management of the entire portfolio, holds the record of every decision, and ensures nothing is dropped or goes quiet.
What You'll Own Single live view of every market-entry/licensing/partnership workstream: stage, blocker, owner, next milestone
Actively monitor slow-moving files; apply pressure when needed
Run weekly planning sessions; prepare portfolio summaries for founder/exec team
Meetings & accountability Prepare briefs, produce records, capture decisions and action items
Structured debriefs after key meetings; hold MD accountable to his own commitments
Commercial support Build commercial cases: cost of entry, licensing/compliance load, tax exposure, partner economics, time to revenue
Research and shortlist local partners/operators; run due diligence




Prepare negotiation briefs (numbers, counterparty, fallback positions) and own follow-through
Regulatory & licensing support Read legislation/licensing conditions directly; produce clear commercial summaries
Work with in-house Legal/Regulatory; track deadlines, renewals, filings
Coordinate external counsel and consultants under MD's direction
Contribute to lobbying/advocacy positions
Thinking partner Draft independent positions, argue counter-cases, challenge the MD when warranted
Bring recommendations, not options lists
Research unfamiliar/pre-regulatory jurisdictions and form a view
Presentations/briefing packs for regulators, partners, founder
Position papers, correspondence, competitor/industry monitoring
Internal: founder, exec team, PM/dev teams, Legal, Finance, Marketing, local market teams
External: regulators, external counsel, GR consultants, commercial partners, industry bodies
Tools Own AI/productivity tooling for the function (research, summarization, drafting, meeting capture)
Requirements 2–5 years in commercial environment (BD, market entry/expansion, corporate development, commercial strategy, transaction advisory, or similar)
Commercial literacy — understands revenue share, CAC, tax/duty exposure, bad deal terms; has contributed to a business case/model a senior person used
Exposure to regulatory/licensing dimension of commercial work
Exceptional organizational discipline across many slow-moving priorities; able to chase non-reports




Strong analytical/research capability — can produce useful output on an unfamiliar jurisdiction within a day
Advanced presentation/spreadsheet skills; genuine AI tool fluency
Excellent written/verbal communication, high attention to detail
High tolerance for ambiguity; comfortable without a playbook
Sound judgement; confidence to raise concerns directly
Exceptional discretion and integrity (handles sensitive info daily)
Works independently, adapts fast to shifting priorities
Background check and confidentiality agreement required
Differentiators (strong advantage) International expansion/new markets experience at a tech or platform company
Regulated industries: gaming/betting, fintech/payments, crypto, cannabis, alcohol, pharma, telecom
Legal training/qualification (commercial, transactional, regulatory) alongside commercial exposure
Corporate development, investment banking, PE, or transaction advisory background
Government relations, public affairs, lobbying, or trade promotion + commercial responsibility
High-growth tech company experience across multiple markets
Willingness to relocate to Europe with the MD within 3–5 years
Also valued Additional languages (French, Spanish, Italian, Portuguese)
Spanish proficiency or commitment to reach it (company-supported tuition)
Total Rewards Salary/level review annually
Bonus up to 50%/year
Direct mentorship from the MD; unmatched exposure to global market entry and senior negotiation
Company-supported relocation to Europe (incl. immigration support)
Birthday gift, branded swag, gym rate, snacks/beverages
Equal-opportunity employer; accommodations available per AODA/Ontario Human Rights Code. AI tools assist application review; all hiring decisions made by humans.

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📌 Manager, New Markets (iGaming) (Ontario)
🏢 Talent Advantage
📍 Ontario