Payroll Onboarding Manager

About Playground

Playground is working to make excellent child care accessible to all. Playground has built best in class software to manage all aspects of running a child care business. We believe that providers should focus on providing incredible child care — the kind of work that only people can do — and that software should manage the rest. We're building the child care management platform that eliminates the administrative work of running a center.

Playground is at an inflection point — and poised to grow extremely fast. We recently raised millions of dollars, have several statewide contracts, and are working with thousands of schools across the country. Additionally, our founders were recently honored as Forbes 30 under 30.

We are a team of owners, who are not afraid to dive into large, complex projects. If you are excited by the prospect of helping build Playground's account management organization and joining a collaborative, high-growth startup — please apply!

About the Role

We’re looking for a Payroll Onboarding Manager to join our team and play a vital role in delivering a smooth, reliable payroll experience for our customers. In this role, you’ll act as a key partner to both clients and internal teams—onboarding new customers, answering payroll-related inquiries, resolving issues in collaboration with our payroll processor, and maintaining clear, up-to-date documentation. Your work will directly impact customer satisfaction and operational efficiency as we scale our payroll offering.

This is a high-impact, customer-facing role perfect for someone who thrives in a fast-paced environment, has a sharp attention to detail, and loves solving problems. You’ll be instrumental in helping clients feel confident and supported throughout their payroll journey, while also enabling internal teams to operate more effectively. If you're excited to join a mission-driven startup and want to make a difference for thousands of child care providers across the country, we’d love to meet you.

What You’ll Do

• Act as a technical expert on payroll operations, supporting both customers and internal teams

• Respond to customer payroll inquiries with clarity, professionalism, and accuracy

• Onboard new clients to Playground Payroll and guide them through a successful first payroll run

• Maintain and update internal and external payroll documentation to ensure consistency and clarity

• Collaborate with our payroll processor to troubleshoot and resolve escalated payroll issues

• Lead informative customer training webinars on key payroll topics and processes

• Continuously identify opportunities to improve payroll support workflows and enhance the customer experience

What You Need

• 2+ years of experience in a customer-facing role, ideally in a support or operations capacity

• 2+ years of payroll experience, with a strong understanding of payroll processes and compliance

• A passion for solving problems and making complex tasks simpler for customers

• Ability to thrive in fast-paced, high-volume environments while staying organized and adaptable

• Strong attention to detail, even when managing multiple priorities at once

• Excellent communication skills—clear, respectful, and effective across email, phone, and chat

• A collaborative mindset and the ability to work cross-functionally with both internal teams and external partners

• Comfort leading webinars or customer training sessions with confidence and clarity

Compensation

• The annual salary range for this position is $90,000 subject to standard withholding and applicable taxes

• Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed range is a guideline, and the range for this role may be modified.

Why Join Playground:

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• Free lunch daily

• New Macbook

• Collaborative and supportive work culture with a high level of autonomy and room for growth

• Help accelerate our mission to make excellent childcare accessible to all!

How to Apply: If you're a hustler who's excited to join a mission-driven, early-stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now. The Playground Team is fully in-office in Union Square, NYC. Please make sure you are open to a fully in-person role before applying.

Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.