Tax Director

Are you looking to grow your career with a team driven by innovation, integrity, and a passion to serve? By joining Dilawri, built on uncompromising excellence and recognized as one of Canada’s Best Managed Companies, you can grow, excel and thrive.

Dilawri is Canada’s largest automotive group, operating more than 80 franchised dealerships and representing over 38 automotive brands across British Columbia, Alberta, Saskatchewan, Ontario, Quebec, and Washington, DC. Since 1985, Dilawri has been committed to delivering exceptional customer experiences by holding themselves to the highest standards of excellence and embracing a future‑focused, innovative mindset.

With a team of more than 4,000 dedicated employees, Dilawri prioritizes collaboration, accountability, continuous learning, and meaningful action—ensuring that customers receive unparalleled service every time they choose to work with us as part of our continual efforts to build trust and strengthen our customer relationships.Our values of Excellence, Teamwork, Innovation, Leading, Integrity and Giving Back underpin who we are, what we do, and how we engage our customers.

Beyond its leadership in the automotive industry, Dilawri is deeply committed to giving back. Through The Dilawri Foundation the organization has contributed tens of millions of dollars to charitable initiatives across Canada, creating long‑term impact in the communities it serves.

Dilawri is full of excitement,click herefor a glimpse of the road ahead.

Summary of Position

We are seeking a senior, highly qualified Tax Director to assume full responsibility for the tax strategy, planning, compliance for the Dilawri Group of Companies, as well as associated family office structures. This key leadership role will provide strategic guidance on tax‑efficient structuring, oversee all corporate and personal/family‑office tax matters, and coordinate with external advisors (legal, tax, accounting) to ensure best practices, and compliance. The ideal candidate will be a pragmatic, solutions‑oriented tax professional with deep technical knowledge, hands‑on experience, and the ability to operate discreetly and collaboratively.The role can be based in either Vancouver BC, or Toronto, ON.

Primary Duties and Responsibilities

• Lead and manage all tax‑related operations across the corporate group: including operating companies, holding companies, real estate companies, partnerships / joint ventures, trusts, and family/foundation or estate entities.
• Design, implement, and maintain tax-efficient structures aligned with long-term investment, wealth preservation, and legacy objectives (including intergenerational planning, trusts, estate freezes, holding-company reorganizations, etc.).
• Oversee work done by outside professionals to ensure timely preparation and filing of all required tax returns and compliance obligations (corporate tax, indirect taxes, trust/estate filings, partnerships), and manage election filings, reorganizations, wind-ups or other corporate‑/entity‑level changes.
• Provide strategic tax advice to senior leadership and stakeholders (executives, owners/family office principals) — including scenario planning, projections, and tax‑impact analysis of proposed transactions, investments, reorgs, M&A, or asset transfers.
• Coordinate with external legal, tax, and accounting advisors to optimize tax outcomes, manage risk, ensure compliance — and where appropriate, transition work in‑house.
• Develop and maintain robust internal tax policies, controls, reporting processes and documentation standards; ensure financial and tax records support both GAAP (or applicable accounting framework) and tax-basis requirements.
• Stay abreast of relevant tax legislation (federal and provincial) and regulatory changes; advise on tax risks, opportunities and compliance implications across jurisdictions (if cross‑border or U.S. holdings are relevant).
• Work closely with finance, legal and other internal functions to support broader financial planning, cash flow management, liquidity needs, inter-company transactions, and consolidation / reporting requirements.
• Provide ad‑hoc support for personal/family office tasks (e.g. wealth & estate planning coordination, trust/estate administration, philanthropic/charitable entity tax reporting, inter‑generational transfers, capital structure planning, family governance if relevant).

Qualifications Required

• Chartered Professional Accountant (CPA) designation (or equivalent); advanced tax credentials or completion of a recognized comprehensive tax course is strongly preferred (e.g. in-depth tax course, Master of Taxation, etc.).
• Minimum of 8–12 years of progressive tax experience, ideally combining public‑practice (accounting/tax firm) and in-house roles; experience working with complex private companies, holding companies, trusts/foundations, and family‑office or wealth‑management structures is a strong asset.
• Demonstrated technical expertise in Canadian corporate tax, trust/estate taxation, partnerships/JVs; some familiarity with cross‑border tax issues is a bonus, where applicable.
• Strong strategic thinking and advisory capabilities — able to analyze complex transactions, model outcomes, and communicate tax implications clearly to non‑tax executives/family principals.
• Excellent leadership, organizational, and project‑management skills; able to prioritize multiple deliverables, manage deadlines, and oversee compliance across multiple entities and jurisdictions.
• High degree of discretion, confidentiality, and integrity — comfortable working with sensitive personal and financial information.
• Excellent interpersonal, communication (written & verbal), and relationship‑management skills — able to liaise with external advisors, legal counsel, senior executives, and family office stakeholders.
• Advanced proficiency with financial and tax‑software tools, and expert-level Microsoft Excel (modelling, cash flow, tax projections).
• Optional but valuable: experience with estate planning, trusts, family governance, succession planning, private equity or real estate investments, and familiarity with multi-jurisdictional corporate/holding structures.
• Pragmatic, solution‑oriented, and proactive — anticipates tax issues and plans accordingly.
• Highly organized, meticulous, able to manage complexity and multiple priorities.
• Collaborative and comfortable working in a small, senior-level team with broad responsibility.
• Ability to explain complex tax concepts simply to non‑tax stakeholders.
• Discreet and trustworthy, especially where personal/family‑office matters are involved.
• Compensation for this role is competitive and aligned with market benchmarks
• Legally entitled to work in Canada.

About Dilawri

In addition to working with and learning from a team of leading professionals in the automative industry, our benefits include:

• Discounted employee vehicle purchase program
• Job-specific coaching & training programs
• Employee wellness & assistance programs
• Employee social events

Build your career with a team that leads meaningful change, invests in its people, fosters an entrepreneurial mindset and strives for excellence every day.