People Operations Generalist

About Us

We are a global learning platform on a mission to motivate every learner by empowering every educator. From K-12 classrooms and universities to corporate training settings, our platform is trusted in over 150+ countries by 75 million monthly active users. In the U.S., 90% of schools use Wayground to engage students and transform learning through technology.

Wayground is a high-growth, profitable SaaS company backed by leading investors including Tiger Global, GSV, and Nexus Venture Partners. If you're excited about education and international SaaS and want to build towards a mission that you can be proud of, then Wayground is the right place for you.

The Role

We're hiring a People Operations Generalist to support the day-to-day operations. This is a hands-on, individual-contributor role focused on execution: you'll handle core People processes - onboarding, payroll, benefits, and more across GTM. It's a great fit for someone who's dependable, detail-oriented, and comfortable owning the day-to-day.

Work Location: This is a hybrid role based in New York City, requiring in-office attendance four days per week.

What You'll Do

People US

• Own HRIS as the system of record: configuration, workflows, reporting, integrations, and data integrity across the full employee lifecycle.
• Run onboarding and offboarding: offer letters, background checks, I-9 and E-Verify, provisioning and deprovisioning, equipment, first-week experience, exit logistics.
• Run semi-monthly US payroll end to end, including off-cycles, corrections, and reconciliation with Finance.
• Administer benefits: open enrollment, carrier and broker management, qualifying life events, COBRA, 401(k) administration and audit support.
• Administer all leave types across states: FMLA, state paid family and medical leave, parental leave, disability, and accommodations, including the tracking and pay coordination behind each.
• Own People spend management: budget tracking, invoice and reimbursement approvals, headcount and benefits cost reporting alongside Finance.
• Serve as the first point of contact for all US employee questions on pay, benefits, policy, and systems.
• Maintain multi-state employment compliance: registrations in new states, required postings and notices, wage and hour, classification, handbook and policy updates.

Legal Operations

• Run contract operations end to end: intake and routing, template management, redline coordination with outside counsel, execution, storage, and renewal tracking.
• Manage the customer legal and security review queue: DPAs, security questionnaires, insurance certificates, and documentation requests.
• Support compliance and certification efforts as program coordinator across internal owners and auditors.

  Work with finance on insurance renewals for the business and benefits with people

Vendor Management (Documentation)

• Own the vendor documentation workflow in Asana: intake, required documentation, approvals, signatures

  Collect and maintain vendor records: W-9s, COIs, security and privacy documentation, signed agreements, renewal and expiration dates.

• Maintain the process itself: keep the Asana project structured so anyone can see where a vendor stands without asking.

What We're Looking For

• 2+ years in People Operations, ideally at a startup or in a fast-moving environment.
• US payroll, benefits, and leave administration experience across multiple states.
• Working knowledge of multi-state US employment compliance.
• Hands-on Rippling experience (or a comparable HRMS) across the full employee lifecycle.
• A process mindset: you spot what's inefficient and fix it, and you document as you go.
• Strong organization and attention to detail, comfortable owning several workstreams at once.
• A collaborative approach: you build trust quickly and make cross-functional partners' lives easier.
• This is a hybrid role based in New York City, requiring in-office attendance four days per week.

What We Offer

• A key role in an exciting journey, we're a company with ambitious targets and meaningful goals
• Fantastic colleagues in a fun, high-energy environment with real opportunities to learn
• Competitive compensation and benefits package
• The chance to work on a meaningful mission helping change how students learn and engage with education around the world

Salary Range

The expected range for this role is $90,000-$120,000 annually

Working at Wayground

• Healthcare coverage for you and your dependents.
• Competitive compensation.
• On-site presence, flexible PTO.
• Additional health, financial, and professional development benefits.

If you are looking for an opportunity to make an impact in the education technology space and contribute to the growth of a fast-paced and innovative company, Wayground is the perfect place for you. Join us in creating engaging learning experiences that inspire students worldwide!