Head of Tax

confidential • Toronto, Ontario • Full Time • $170,000–$200,000 / year

Posted on Mon, Oct 5, 2026

This is a newly elevated seat at a company that's outgrown its old tax structure faster than it can backfill it, not a caretaker role stepping into someone else's system. You'd be the CFO's direct tax partner across two countries, building the U.S. function from the ground up while a lean, trusted team already in place gives you real runway to make it yours from day one.
COMPANY

Corporate headquarters in Toronto, with a growing footprint of nearly 600 healthcare locations across Canada and expansion underway into the U.S.
One of the largest and fastest-growing industry services platforms in Canada, built through an active, ongoing acquisition strategy.
Backed by private equity, following a path from privately held to publicly traded and back to private ownership, a transition the current tax team has lived through firsthand.
Long-tenured senior leadership; the outgoing tax leader on this team has been with the company more than a decade.
Profitable, well-funded, and actively scaling, with expectations to double in size within five years.

COMPENSATION PACKAGE

Base salary $170,000 to $200,000 CAD, based on experience and qualifications.
Bonus eligible. Confirmed target is meaningful (up to 25%); exact structure to be finalized
Hybrid model: four days on-site Monday through Thursday, with Fridays remote.

ADVANTAGES

Blank-slate scope. This role was elevated rather than backfilled, so there's no legacy job description or predecessor's playbook to inherit; you shape it.
Direct CFO access. You report straight to the CFO and become their primary tax voice, including on the U.S. side, where the CFO has no in-house expertise to lean on.
Ground-floor U.S. build. The company's U.S. structure is new and still straightforward, giving you the chance to build it out rather than untangle someone else's mess.
Real growth trajectory. The business has scaled through private, public, and back to private ownership, with location count nearing 600 and plans to double within five years.
Built-in technical support. The former VP of Tax remains available to the team as a resource during the transition, so the ramp-up isn't solo.
Lean, high-trust team. A two-person tax function that works closely with Reporting, Corp Dev, Treasury, and Legal, in a culture that rewards people who roll up their sleeves over people who delegate.

POSITION DESCRIPTIONThis is a newly elevated seat, created because the company's growth and cross-border expansion outpaced what the prior Director of Tax structure could support. The Head of Tax will lead both Canadian and U.S. tax functions and serve as the CFO's primary tax partner across compliance, provision, M&A, and audit defense.

Lead Canadian and U.S. tax compliance and serve as principal contact for CRA and IRS audits in both jurisdictions.
Manage tax compliance and elections tied to ongoing business practice acquisitions, supporting M&A activity end to end.
Own the quarterly and annual income tax provision for both jurisdictions, including related disclosures.
Oversee transfer pricing policy and documentation across cross-border entities.
Track all Canadian and U.S. filing deadlines and provide oversight of tax payments and account reconciliations.
Partner with Controllership and external auditors on uncertain tax positions, purchase accounting, and financial statement disclosure.
Monitor and respond to Canadian and U.S. tax changes affecting the organization's structure.
Present tax matters directly to the CFO and, as needed, the Audit Committee and external auditors.
Manage and mentor one direct report, with the expectation of running the day-to-day independently rather than requiring close oversight.

IDEAL CANDIDATE

10 to 12+ years of progressive tax experience, with demonstrated depth in both Canadian and U.S. tax, not exposure to one and familiarity with the other.
Big 4 foundation, ideally followed by in-house experience at a public company or a PE-backed acquirer.
Hands-on experience with M&A tax and cross-border transfer pricing, gained in a business that acquires on a recurring basis rather than episodically.
Comfortable owning quarterly and annual provision work (ASC 740 / IAS 12) and standing as the primary contact through CRA and IRS audits.
Canadian CPA required; U.S. CPA, MST, or in-depth tax course is an asset, not a requirement.
A builder who drives projects to completion without being pushed. This is a direct response to what didn't work in the prior seat.
Comfortable running a lean, two-person function supporting close to 600 locations and monthly acquisition volume, with minimal hand-holding from above.
Not a fit: someone who needs heavy oversight to keep initiatives moving, or who leads by directing rather than collaborating.

More live head_of_tax roles

Browse all live jobs · Accounting & finance salary data

View the interactive listing →