Senior Tax Manager

The Opportunity - Senior Tax Manager (Remote - USA / Canada)

We are looking for a Senior Tax Manager, to own the tax function end to end, from corporate income tax to sales and indirect tax to cross-border compliance. You will be the sole in-house tax expert partnering directly with Finance, Product, and external advisors. This is a rare opportunity to build a tax function from the ground up at a high-growth company, set the standard for how we file, plan, and shape the tax logic embedded in the products our customers use every day.

What You’ll Do:

• Own corporate and income tax compliance and provision, including federal, state, and local filings, quarterly estimates, and coordination of the annual return with external advisors.

• Manage sales and indirect tax across all jurisdictions we operate in, including nexus determination, registration, filing, and audit response.

• Scope, select, and implement a tax engine if needed, integrating it with our ERP (Rillet) and internal systems to automate tax calculation at scale.

• Manage Canadian tax obligations and correspondence with the Canada Revenue Agency, covering GST/HST, provincial sales taxes, SRED and cross-border matters tied to our EOR model.

• Research technical tax positions and translate that research into documented, defensible filing positions and internal policy.

• Partner with Product and Engineering to design the tax structure of customer invoices, ensuring the right taxes are assessed, displayed, and remitted.

• Advise leadership on tax planning, exposure, and prudent positions as the business enters new jurisdictions and launches new products.

• Manage relationships with third-party tax advisors, auditors, and taxing authorities, directing outside work while retaining in-house ownership where possible.

What You'll Have:

• A bachelor's degree in accounting, taxation, or finance; a Master of Science in Taxation (MST) or equivalent graduate tax focus is a plus.

• Eight or more years of progressive tax experience spanning corporate/income tax and sales/indirect tax, ideally built on a foundation in public accounting (Big Four or regional firm) before moving in-house. Generalists who have carried multiple tax disciplines are strongly preferred over narrow specialists.

• Hands-on experience implementing or administering a tax engine and integrating it with an ERP.

• Working knowledge of ASC 740 tax provision and the corporate compliance cycle, from estimates through the annual return.

• Foreign or international tax experience, ideally including Canadian tax (GST/HST, provincial sales tax) and direct interaction with the Canada Revenue Agency.

• Proficiency with tax research platforms (Checkpoint, Bloomberg Tax, or CCH) and the ability to research tax law independently and turn findings into documented, defensible filing positions.

• Strong organization and self-sufficiency; you can run a full tax function as a team of one and prioritize across competing deadlines.

• Foreign or international tax experience, ideally including Canadian tax and direct interaction with the CRA.

• A track record of advising cross-functional partners (Finance, Product) and influencing decisions with clear, practical guidance.

• CPA (or CPA, Ontario / equivalent) preferred but not required.

Why Join Us

• Unlimited Paid Time Off

• Work from anywhere in Canada and USA

• Health and Dental benefits

• Up to 2% matching RRSP / 401K

• Learning and Development opportunities

Apply Now

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