We are looking for an experienced tax specialist to support cross-border tax reporting and withholding compliance for a complex financial services environment in Toronto or Waterloo, Ontario. This position plays an important role in meeting Canadian and U.S. tax obligations related to intermediary requirements, FATCA, and Common Reporting Standard reporting. The successful candidate will work closely with internal stakeholders to strengthen reporting accuracy, maintain current procedural guidance, and help ensure regulatory expectations are met. This role requires employees to be on site 2 days per week, either in their office in Waterloo or Toronto. For a highly qualified candidate, other Canadian office locations would be considered (Montreal, Halifax, Winnipeg, Calgary, Vancouver, etc).

Responsibilities:

• Prepare U.S. tax filings and information slips associated with intermediary obligations, including annual returns and investor reporting documents.

• Assess W-8 and W-9 documentation to confirm completeness, accuracy, and suitability for withholding tax purposes.

• Monitor withholding activity to verify that tax is applied correctly in line with applicable regulatory and reporting rules.

• Lead the periodic intermediary review process by gathering supporting records, coordinating with external reviewers, and addressing follow-up questions.

• Complete annual reconciliations related to U.S. tax reporting, including comparisons between reported withholding amounts and remittances made by the organization or other withholding agents.

• Track legislative and regulatory developments affecting intermediary, FATCA, and Common Reporting Standard requirements, and put necessary updates into practice.

• Maintain and revise internal tax procedures, reference materials, and compliance documentation to reflect current obligations.

• Provide practical tax guidance to operational teams to support accurate execution of day-to-day processes and reporting activities.

• Minimum of 4 years of experience in tax, with exposure to compliance, reporting, or withholding in a corporate or financial services setting.

• Working knowledge of U.S. tax reporting requirements, including forms such as 1042, 945, 1042-S, 1099-DIV, and 1099-B.

• Familiarity with withholding tax documentation, including the review and validation of W-8 and W-9 forms.

• Understanding of Canadian and international tax compliance frameworks, including QI, FATCA, and Common Reporting Standard (CRS) requirements.

• Experience performing reconciliations, research, and audit-support activities with strong attention to detail.

• Ability to interpret regulatory updates and translate technical requirements into effective business processes and documentation.

• Strong written and verbal communication skills, with the ability to collaborate across teams and support external review activities

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