Cross-Border Tax & Compliance Manager

Cross-Border Tax & Compliance Manager

We’re looking for a hands-on, cross-border tax professional to own Canadian and U.S. tax compliance within a Canadian parent / U.S. operating subsidiary structure. This role goes well beyond filings. The right person thinks in systems, builds scalable processes, and actively looks for ways to automate recurring tax and compliance work, freeing up time for higher-value, strategic initiatives.

Who we are:

At the Crimson Group, we provide our clients with high-value automation, instrumentation, electrical design, and process operation solutions.  With the capabilities of a large enterprise, and the agility and responsiveness of a small company, we are a customer-focused provider of automation and integrated solutions. Crimson Group provides total integration of design, project management, panel manufacturing, installation/commissioning, maintenance, and repair for North America and select international markets.

What we Offer:

Competitive compensation

Comprehensive benefits package, including an RRSP plan

A culture of continuous learning with real opportunities for growth and skill development

The opportunity to give back through charitable initiatives supported by our RedTail Community Foundation

What You Will Be Doing:

Cross-Border Corporate Tax

Own Canadian T2 corporate tax filings, including foreign affiliate considerations

Own or directly coordinate U.S. federal corporate filings (Forms 1120 / 1120-F)

Manage intercompany transactions, including management fees, cost allocations, and transfer pricing awareness

Coordinate with Canadian and U.S. external tax advisors

Address withholding tax considerations (Part XIII / FDAP)

U.S. State & Local Tax (SALT)

Manage U.S. state income and franchise tax compliance

Perform Nexus analysis (economic vs. physical)

Oversee sales and use tax compliance and audits

Coordinate multi-state filings

Experience with tools such as Avalara / AvaTax strongly preferred
(Experience in TX, NM, or CO is a plus, but adaptability across states is more important.)

Cross-Border Individual Tax Awareness

Understand implications for Canadian employees working in the U.S. (e.g., E-2 context)

Coordinate payroll considerations (T4 vs. W-2)

Maintain awareness of permanent establishment risks

Apply foundational Canada–U.S. tax treaty concepts
(Not a personal tax preparer role, but able to identify and flag issues early.)

Required Skills and Qualifications:

Strategic & Business Capabilities

Participate in tax planning discussions, including entity structuring, cash movement, and transfer pricing

Translate tax implications into clear, practical business language

Confidently and constructively challenge external advisors when needed

Experience in mid-market, PE-backed, or growth-oriented organizations strongly preferred

Automation, Systems & Workflow Design

Experience designing end-to-end tax and compliance workflows

Strong process mindset, including documentation, controls, and exception handling

Comfortable partnering with finance teams and working within ERPs (NetSuite or similar)

Interest in—or hands-on experience with—automation tools such as:
o Workflow and orchestration tools (n8n, Replit, or similar)
o Low-code / no-code platforms (Zapier, Make, Retool, etc.)
o Basic scripting, SQL, or Python for data transformation
o AI-assisted workflows for document review, reconciliations, and variance analysis

Preferred Skills and Qualifications:

Exposure to captive insurance structures (e.g., §831(b), reserve deductibility, premium flows)

Experience supporting captive-related filings, audits, or advisor coordination

Ideal Background

CPA (Canada or U.S.); dual CPA is a strong plus

7–12 years of relevant tax experience

Mix of public accounting and industry, or deep industry experience with advisor management

Comfortable operating in ambiguity and building as they go

**As part of our commitment to maintaining a safe and professional work environment, the Crimson Group of Companies conducts comprehensive background checks and drug and alcohol testing on all prospective employees as part of the final offer process. These checks are intended to verify the accuracy of information provided by candidates and assess any potential risks to the company or its employees. All offers of employment are contingent upon the successful completion of these background checks.**

Please note: We do not accept phone calls regarding job opportunities. To ensure fairness and consistency in our hiring process, all candidates must follow the application instructions outlined in the posting. Thank you for your understanding.