Senior HR Advisor, Escalations in Toronto, Ontario at Rippling

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.

Expanding globally used to mean establishing legal entities in every new country, a process taking months and costing tens of thousands of dollars. As an Employer of Record (EOR), we change that. We legally hire employees on behalf of our client companies through our own established global entities. We handle local payroll, benefits, taxes, and compliance so our clients can hire the best talent anywhere in the world in minutes.

As our Senior HR Advisor, Escalations you will be the central nerve center for our most critical, high-impact Employer of Record (EOR) escalations across the globe. Acting as a strategic, individual-contributor lead, you’ll step into high-severity scenarios, spanning international employment law, complex payroll/benefits issues, and cross-border employee relations and orchestrate seamless, compliant, and client-centric resolutions.

• Lead Critical Escalations: Take full ownership of end-to-end, high-severity client escalations across multiple countries and time zones, acting as the primary point of contact during elevated retention-risk events.
• Navigate Complex International HR & ER: Partner with local HR Advisory and Legal teams to manage complex employee relations issues and cross-border terminations within diverse regulatory and labor law frameworks.
• Drive Cross-Functional Alignment: Assemble and orchestrate cross-functional "war rooms" across Payroll, Benefits, Legal, Product, Sales, and Ops to align on strategy, remove roadblocks, and execute solutions.
• Be the Strategic Client Contact: Deliver direct, transparent, and empathetic communication to client executives and HR leaders during crisis moments—building trust, setting realistic expectations, and mitigating churn risk.
• Structure Triage & Governance: Define escalation severity, run intake assessments, map out actionable resolution plans, and ensure clear documentation and milestone tracking throughout the process.
• Conduct Post-Mortems & Process Fixes: Perform root-cause analyses post-resolution, identifying systemic gaps and collaborating with cross-functional teams to implement long-term preventative controls.

• 8+ Years of Relevant Experience: Background in global HR operations, EOR/PEO services, client escalation management, or leading complex, cross-functional global programs.
• Global HR & Regulatory Knowledge: Working familiarity with international employment frameworks, global HR compliance, and cross-border operational nuances.
• Client & Executive Presence: A proven track record of de-escalating high-stress situations with senior stakeholders, executives, and clients contemplating churn.
• Influence Without Authority: Demonstrated ability to drive consensus, mediate conflicts, and align cross-functional teams toward a single solution without direct team management responsibilities.
• Structured Problem Solving: Deep analytical skills with a knack for root-cause investigations, project management, and delivering concise executive-level updates.
• Global Flexibility & EQ: Exceptional emotional intelligence, composure under pressure, and the flexibility to support urgent escalations across time zones as needed.

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 one to three days a week under current policy, to be an essential function of the employee's role. This role is eligible to be fully remote for those based in British Columbia and or Quebec.

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#LI-remote

This role will receive a competitive salary + benefits + equity. 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.