Company Description Play.

Fiscalité Athlètes

Professionnels is a boutique cross-border tax firm dedicated exclusively to professional athletes, with a strong focus on NHL players, referees, coaches, executives, and their advisors. The firm also serves clients in other professional sports, including the NFL and MLB, whose careers span multiple provinces, states, and countries. Founded by Jason Chevrier, CPA, M.Fisc., a Big Four-trained tax professional with nearly two decades of Canada-U.S. tax experience, Play combines deep technical expertise with an educational approach that helps clients understand tax implications before decisions are made. In addition to the tax filing services, the team provides proactive guidance on cross-border tax planning, residency, trades and free agency, retirement strategies, corporate structures, and tax-efficient, often in close collaboration with player agencies, financial advisors, and family offices. The firm offers bilingual service in English and French and is committed to long-term relationships built on trust, responsiveness, and technical excellence.

Role Description As a Tax Specialist – Pro Athlete, you will provide specialized cross-border tax advisory and compliance services to professional athletes and their related entities. Day-to-day responsibilities include preparing and reviewing Canada-U.S. tax returns, analyzing residency status and multi-jurisdictional tax exposure, and advising on tax implications of trades, free agency moves, and contract structures.



You will support planning for 401(k), Roth strategies, Retirement Compensation Arrangements (RCAs), and other tax-efficient investment and corporate structures, while communicating complex tax concepts in clear, accessible terms.

The role involves regular collaboration with player agencies, financial advisors, and family offices to align tax strategy with overall financial and career objectives. This is a full-time, and while our office is located in Montreal, QC all of our team is working remotely.

Qualifications

- Strong knowledge of Canada-U.S. cross-border tax rules, including residency, multi-jurisdiction filing requirements, and tax treaty application.
- Experience with personal, corporate, and trust tax compliance and planning, including high-net-worth or professional client profiles.
- Ability to interpret and apply tax legislation and guidance, conduct technical research, and prepare clear written recommendations.
- Demonstrated skill in explaining complex tax concepts in simple, practical language to clients and non-tax professionals.
- Excellent organizational skills, attention to detail is key, and ability to manage multiple deadlines in a fast-paced, client-centered environment.
- Robust interpersonal skills, collaborative mindset, and professionalism when working with agents, advisors, and family offices.
- Proficiency with tax preparation software (CCH Axcess and Taxprep), Microsoft Excel, and other

📌 Tax Specialist - Pro Athlete (Montreal)
🏢 Play. Fiscalité Athlètes Professionnels
📍 Montreal