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Director of Human Resources in Toronto, Ontario at Syndesus

NewEmployment Type: Full-Time
Syndesus
Toronto, Ontario, Canada
Posted on
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Job Description

Job Summary
We are seeking an experienced Director of Human Resources to lead the global human resources function from the Toronto office. This role will be responsible for overseeing all HR compliance, payroll, and administrative matters across a growing international footprint, while building scalable people processes that support a high-performance organization. The HR Director will also serve as a strategic advisor to leadership on workforce planning, organizational design, and talent strategy as the company scales. This role reports directly to senior executive leadership.

The Director will ensure full compliance with employment laws and payroll regulations across the company's operating jurisdictions in North America and internationally. This leader will own multi-country payroll oversight, benefits administration, policy development, onboarding, regulatory compliance, and core HR operations, ensuring rigor, accuracy, and consistency across regions.

In addition to compliance and operational excellence, the Director will play a key role in talent acquisition and onboarding, partnering closely with leadership to support recruiting efforts and deliver a best-in-class employee experience. The ideal candidate brings strong expertise in US and Canadian labor law, deep experience managing multi-country payroll and compliance frameworks, and thrives in a fast-scaling environment.

Core Responsibilities
  • Own and oversee all HR compliance and administrative matters across the company's operations, ensuring adherence to employment laws, regulatory requirements, and internal policies.
  • Lead and manage multi-country payroll operations. Ensure accuracy, timeliness, and coordination with external payroll providers and advisors.
  • Develop, implement, and continuously improve HR policies, employee handbooks, and compliance frameworks in alignment with evolving labor laws and business needs.
  • Serve as the primary internal expert on applicable labor laws in the company's operating jurisdictions, advising leadership on employment matters, risk mitigation, terminations, documentation, and regulatory changes.
  • Oversee benefits administration across jurisdictions, ensuring competitive offerings, regulatory compliance, and effective vendor management.
  • Manage all core HR operations, including employee records, contracts, immigration coordination (as applicable), leave management, and statutory reporting requirements.
  • Design and scale onboarding processes to deliver a consistent, high-quality new hire experience across regions, ensuring proper documentation, systems setup, and compliance from day one.
  • Partner with leadership to support recruiting efforts, including interview process design, candidate evaluation frameworks, offer structuring in coordination with legal and finance, and ensuring compliant hiring practices.
  • Build scalable HR infrastructure, systems, and processes to support continued growth.
  • Collaborate cross-functionally with Finance, Legal, and executive leadership to ensure alignment between people strategy, compliance, and company objectives.
  • Proactively identify operational risks and implement structured processes to improve accuracy, efficiency, and employee experience across the organization.

Qualifications
Required
  • Bachelor's or Master's degree in Industrial-Organizational Psychology, Organizational Behavior, HR Management/Development, or a closely related field.
  • 10+ years of progressive Human Resources experience, including senior-level ownership of HR operations, compliance, and payroll functions.
  • Deep expertise in United States labor law, payroll administration, and compliance management.
  • Strong working knowledge of Canadian employment law, payroll regulations, and statutory requirements.
  • Demonstrated experience overseeing multi-country payroll operations, including coordination with external payroll providers and local advisors.
  • Proven track record of managing HR compliance across multiple jurisdictions in a growing organization.
  • Hands-on experience with onboarding processes, employment documentation, and HR administrative systems.
  • Experience supporting recruiting efforts and partnering with hiring managers to ensure compliant and effective hiring practices.
  • Experience building HR infrastructure in a scaling, multi-entity organization.
  • Strong operational rigor with exceptional attention to detail and documentation accuracy.
  • Ability to operate independently in a fast-scaling environment while building structured, repeatable processes.
  • High level of integrity, discretion, and professionalism when handling confidential information.
  • Excellent communication skills with the ability to advise senior leadership on employment, compliance, and risk-related matters.
  • Legally authorized to work in Canada (Canadian citizenship, permanent residency, or valid work visa required).
Preferred
  • Experience managing payroll and compliance in additional international jurisdictions.
  • Background in a professional services or high-growth environment.

Recruiting Process
The recruitment process is designed to ensure a thoughtful evaluation of candidates and alignment with the team's objectives and company values. The process typically involves interviews with senior leadership, conversations with executive stakeholders, and a final in-person round.

AI Use Disclosure — AI tools may be used to support the screening and assessment of applicants for this role.

Accessibility in Recruitment — Accommodation is available during any stage of the recruitment process; please notify the recruiter in advance.

Benefits
The company offers a competitive total rewards package, which includes:
  • Market-benchmarked salary and bonus structure.
  • Equity opportunities for select positions.
  • Visa sponsorship for eligible candidates.
  • RRSP plan with employer matching contributions.
  • WSIB coverage as required by Ontario law.
  • Professional development sponsorship for training, conferences, and certifications.
  • Meal and wellness reimbursements, subject to applicable limits.
  • Commuter benefits leveraging available tax concessions.
  • Relocation assistance for eligible candidates.
  • Paid time off accrued in accordance with the Ontario Employment Standards Act.
  • All Ontario statutory holidays plus additional company holidays.
  • Comprehensive healthcare, vision, and dental insurance through Canadian providers.
  • Family-building, mental health, and health navigation support.
  • Short-term disability insurance through a Canadian provider, exceeding Employment Insurance requirements.
  • Paid sick days as required under the Ontario Employment Standards Act.
  • Statutory leaves of absence as required by the Ontario Employment Standards Act, 2000 (ESA), including pregnancy, parental, caregiver, and bereavement leave.
  • Reasonable accommodation for qualified individuals with disabilities in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act (AODA).

Work Arrangement
This role is based primarily at the Toronto office, with a significant in-office expectation. The company believes in-office presence supports the collaboration and connection that drive strong outcomes. Some remote flexibility may be available at the discretion of the manager based on team needs and individual performance.

Diversity, Equity, and Inclusion Statement
The company is committed to providing equal employment opportunities and fostering a workplace free from discrimination and harassment. In accordance with the Ontario Human Rights Code and Employment Standards Act, employment decisions are made solely on merit, qualifications, and bona fide occupational requirements. The company does not discriminate against any individual based on race, ancestry, place of origin, colour, ethnic origin, citizenship, creed, sex, sexual orientation, gender identity, gender expression, age, record of offences, marital status, family status, or disability.

Applications from all qualified candidates are encouraged, and applicants' needs will be accommodated under the Ontario Human Rights Code throughout the recruitment and selection process.

Job Location

Toronto, Ontario, Canada

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