Manager, New 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 setting (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) (Winnipeg)
🏢 Talent Advantage
📍 Winnipeg