Senior HR Generalist

Role Description

We're looking for a Senior HR Generalist to join Wonolo's People team. This is a hands-on, full-scope role for someone who genuinely likes wearing multiple hats — one week you might be deep in a benefits question, the next you're auditing pay equity data, drafting a new policy, or jumping in to help Recruiting push through a hiring surge. You'll be a key operator on a lean team, which means real ownership and real visibility into how People work shapes the company.

This is a great fit for someone who's energized by modern ways of working, including using AI tools to work smarter, not just faster.

What you'll do:

• HR Operations
  • Serve as a go-to resource for employees and managers on day-to-day HR questions
  • Support pay equity and pay transparency data entry, auditing, and reporting
  • Own or support key people processes: onboarding/offboarding, leave administration, employee records, and lifecycle transactions
  • Support the performance management lifecycle
  • Draft and maintain documentation (policies, guidelines, forms, and process docs) that are clear and usable, not just compliant
  • Support employee relations matters (performance concerns, accommodation requests, and separations) with discretion and sound judgment
• Benefits Administration & Compliance
  • Assist in the administration of day-to-day benefits programs across the US and Canada, including benefits enrollment, vendor coordination, equity grant processing, and employee questions
  • Help evaluate and improve benefits offerings and identify opportunities to simplify administration
  • Stay current on North American (US and Canada) labor laws and regulations to keep the organization compliant
  • Support audits, EEOC reporting, and other compliance-related documentation
  • Ensure compliance of the company policies and procedures including developing and/or revising policies and procedures, implementing standard operating procedures that are aligned with applicable labor requirements
• Process & Continuous Improvement
  • Compile and analyze HR metrics to support data-driven decisions
  • Lead or contribute to initiatives that streamline and automate People workflows
  • Bring an experimental mindset to using AI tools in day-to-day HR work; from documentation to process design
  • Identify opportunities to improve policies and ensure the company is operating securely, scalably, and effectively
• Recruiting & Talent (as needed)
  • Provide surge support to the Recruiting/Talent team during periods of increased hiring need — sourcing, screening, or interview coordination
  • Step in flexibly without owning a standing requisition load

Qualifications

• 4+ years of HR generalist experience spanning HR operations, benefits, and compliance
• Working knowledge of North American labor laws, compliance requirements, and HR best practices
• Comfortable with detailed data entry and auditing work (e.g., pay equity/transparency reporting) as well as higher-level process design
• Comfortable moving between strategic and tactical work; you can build a process and also run it
• A clear, direct communicator who documents things well and treats people like adults
• Curious about and open to using AI tools to improve how HR work gets done

Requirements

• If you have read up to this point, we hope you are excited about this opportunity to work at Wonolo! Even if your experience does not check every bullet point, we still highly encourage you to apply. The best hires do not always check off every box of a job description.

Nice to haves

• Hands-on experience with AI tools applied to People/HR use cases
• Experience with modern HRIS platforms, especially Rippling
• Experience supporting HR through M&A or org change
• Prior recruiting or talent acquisition exposure, even if informal

Pay Range

The expected pay range for this position is $103,500 - 155,000/year CAD. Please note that individual total compensation for this position will be determined at the Company's sole discretion and may vary based on several factors, including but not limited to, location, skill level, and years and depth of relevant experience. Additionally, this role is currently eligible to participate in Wonolo’s equity plan as well as a range of health and wellbeing, retirement savings, and other benefits within a holistic total rewards offering.

Benefits

• The opportunity for growth in a mission-driven and well-funded start-up
• Meaningful equity
• We pay 100% of the medical/dental/vision insurance premiums for you
• Generous parental leave plan
• Cell phone reimbursement and company laptop
• Retirement plans as well as life and disability insurance
• Access to no-cost on-demand mental health support, including counselling, mindfulness and meditation, and wellbeing courses
• We encourage a healthy work-life balance and offer flexible schedules, an open vacation policy, and the ability to work from anywhere in the U.S. or Canada (no more commutes!)
• Team outings, happy hours, company off-sites, and more!