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 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




- Solid 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-prospect 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) (Toronto)
🏢 Talent Advantage
📍 Toronto