Apply on Kit Job: kitjob.ca/job/2g9glw

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.

We are looking for a highly-motivated, business‑minded attorney to join as Counsel, HR Products on the Legal & Compliance team. In this role, you will partner closely with Product, Sales, and Compliance and report to our Assistant General Counsel, HR Products. You will provide key legal guidance to our business team as we launch our Employer of Record ("EOR") services in new countries and provide ongoing product and employment counseling across our launched EOR countries. You will also serve as product counsel to our HR product teams more broadly, including the Professional Employer Organization ("PEO") and Perks products. You are a self‑starter, excited to learn about new jurisdictions and new areas of law, a strategic thinker who wants to build a world‑class, highly efficient product counsel function at a rapidly growing company, and you have a passion for providing creative, proactive, and pragmatic legal guidance.

You Will

Provide employment counsel to our EOR HR and PEO Advisor teams.

Analyze and provide product counseling on employment rules and regulations and how to compliantly hire and offboard employees through an EOR in different jurisdictions.

Prepare employment agreement templates, termination notice and agreement templates, and policy documents for our EOR.

Provide advice to Product on insurance licensing and insurance regulatory compliance (including ERISA and COBRA).

Partner with our Product, Operations, Business Development, Sales,



and Client Services teams to build and manage Rippling’s product counseling function.

Navigate complex regulatory frameworks in the U.S. and abroad to create scalable and innovative solutions for our products and services.

Drive the compliance culture at Rippling and embed integrity and compliance in all of our operations as our company grows.

Advise and assist with Rippling’s general legal needs as they arise.

You Have

3+ years of experience in-house or at a law firm.

Substantive knowledge of and experience with employment law.

Law degree (e.g., JD or equivalent).

Experience with PEOs or EORs (preferred).

Entrepreneurial mindset, solution‑oriented ethos, and ready to roll up your sleeves.

Passion for efficient processes.

Strong project management and organizational skills.

Excellent drafting and written and verbal communication skills with the ability to break down complex legal jargon into easy‑to‑understand and practical advice.

Strong analytical and problem‑solving skills.

Sense of humor.

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, disability, medical condition, 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 [email protected].

This role will receive a competitive salary, benefits, and equity. The salary for US‑based employees will be aligned with one of the ranges below based on location: 156,000 – 260,000 USD per year (US) and 120,000 – 200,000 CAD per year (CA).

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Apply on Kit Job: kitjob.ca/job/2g9glw

📌 Counsel, HR Products (Toronto)
🏢 Rippling
📍 Toronto