Canada post Jobs in Caledon, ON

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system. Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @ Rippling.com addresses.

What is an employer of record (EOR)?

An Employer of Record (EOR) is a service provider that allows companies to legally hire and work with employees in foreign countries without establishing their own legal entity in that country. This is made possible through a legal arrangement where the EOR establishes its own legal entity in the country and hires employees on behalf of the client company. This arrangement offers a viable solution for companies that wish to expand their global reach without investing in setting up a legal entity in every country where they operate.

About the role

We are looking for an experienced and strategic Regional Manager to lead a team of HR Advisors across Canada. These Advisors oversee the full employee lifecycle, from onboarding and compliance to employee relations and HR operations. As the Regional Manager, you will provide leadership, drive process improvements, and ensure exceptional service delivery while empowering your team to act with autonomy.

This role requires a blend of strategic leadership, hands‑on problem‑solving, and cross‑functional collaboration. You will oversee operations, manage escalations, and act as a bridge between HR Advisors and internal teams such as Legal, Compliance, Product, Sales, and Implementation.

What you will do

Leadership & Team Development

• Manage and mentor a team of 6-7 Senior HR Advisors, fostering their professional growth and ensuring high performance.
• Provide coaching and guidance on complex HR and compliance matters, helping Advisors develop expertise in multi‑country employment laws.
• Foster a high‑performing, solutions‑oriented team culture that prioritizes client service and operational excellence.
• Serve as the primary escalation point for complex HR and compliance matters, collaborating with Legal, Compliance, and other stakeholders to resolve issues effectively.
• Support Advisors in navigating employee relations cases, including terminations, claims, leave management, and regulatory risks.
• Make quick, strategic decisions on HR and compliance matters while balancing risk, business needs, and employee experience.

Process & Compliance Oversight

Cross‑Functional Collaboration & Project Management

Performance & Operational Excellence

What you will need

What Sets You Apart

Additional Information

Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email accommodations@rippling.com

Rippling highly values having employees working in‑office to foster a collaborative work environment and company culture. Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role. This posting is for an existing vacancy. #LI-Hybrid

A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.

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