People Operations Generalist
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Before you apply
Salary$90k – $120k
LocationNew York
Work modeon-site
Typefull-time
SeniorityMid
Experience2+ yrs
DepartmentPeople & Culture, People Operations
Company size51–200 people
PostedOct 9, 2026 · 3w ago
Verified live20h ago
At a glanceSummarised by Seekless from the posting.
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
Skills
Rippling
Asana
Benefits
Health insurance
PTO
401(k)
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
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Own HRIS as the system of record: configuration, workflows, reporting, integrations, and data integrity across the full employee lifecycle.
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Run onboarding and offboarding: offer letters, background checks, I-9 and E-Verify, provisioning and deprovisioning, equipment, first-week experience, exit logistics.
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Run semi-monthly US payroll end to end, including off-cycles, corrections, and reconciliation with Finance.
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Administer benefits: open enrollment, carrier and broker management, qualifying life events, COBRA, 401(k) administration and audit support.
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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.
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Own People spend management: budget tracking, invoice and reimbursement approvals, headcount and benefits cost reporting alongside Finance.
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Serve as the first point of contact for all US employee questions on pay, benefits, policy, and systems.
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Maintain multi-state employment compliance: registrations in new states, required postings and notices, wage and hour, classification, handbook and policy updates.
Legal Operations
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Run contract operations end to end: intake and routing, template management, redline coordination with outside counsel, execution, storage, and renewal tracking.
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Manage the customer legal and security review queue: DPAs, security questionnaires, insurance certificates, and documentation requests.
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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)
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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.
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Maintain the process itself: keep the Asana project structured so anyone can see where a vendor stands without asking.
What We’re Looking For
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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
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A key role in an exciting journey, we’re a company with ambitious targets and meaningful goals
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Fantastic colleagues in a fun, high-energy environment with real opportunities to learn
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Competitive compensation and benefits package
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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
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Healthcare coverage for you and your dependents.
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Competitive compensation.
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On-site presence, flexible PTO.
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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!