Payroll Specialist

Join Cartwheel to help tackle the student mental health crisis.

Cartwheel is an early-stage company building a new kind of mental health program for kids that puts schools at the center. We see our role as supporting school staff who see kids every single day. Instead of going around them, we collaborate with them. This means:

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student's life
  
  

Kids shouldn't just aspire to get out of bed and drag themselves to class. They should be able to experience joy. They deserve to envision and build a life they're excited to live. If you join Cartwheel, you'll help make this vision a reality for millions of students across the country. We're backed by top investors including Menlo Ventures, Reach Capital, General Catalyst, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

About The Role

Cartwheel is a successful and growing telehealth platform revolutionizing access to mental health care for schools, students, and families. We work with nearly 200 school districts to provide life-saving mental health services to a diverse population (50-50 Medicaid/Commercial mix).

We're scaling quickly – from about 1,500 therapy sessions per week across 9 states today to more than double the number of sessions across 20 states in the next year.

As Cartwheel's Payroll Specialist, you will be responsible for payroll processing at Cartwheel, ensuring employees and contractors are paid accurately, on time, and in compliance with federal, state, and local requirements. This role requires foundational knowledge of best practice payroll processes and a drive to innovate and improve. You will report to the Head of People & Culture, and work alongside our Head of Finance and Clinical Operations Team on general payroll matters. You will also work with our Product, Engineering, and Clinical Operations team to inform and support our innovative therapist compensation model.

Role type: This is a W2, Full-Time, Salaried position

Location: Remote in the United States

Start date: Spring 2025

Reports to: Head of People & Culture

What You'll Do

In your first 30 days, you'll:

• Learn the ins and outs of Cartwheel's payroll systems, processes, and start identifying process improvements in payroll operations
• Become proficient in the systems we use, including Rippling, Healthie, our own Cartwheel SaaS app, Google Sheets, Salesforce, Guru, Asana, Slack and other Google Suite apps
• Start managing cross-functional relationships that impact payroll
• Get to know the team!
  
  

Ongoing, you will:

• Coordinate and perform a variety of complex duties in the preparation, processing, and maintenance of payroll, salary, and benefit data so that client employees and contractors are always paid accurately and on time.
• Identify opportunities in Rippling and other systems to improve the accuracy and efficiency of our payroll processes.
• Research and analyze discrepancies and process appropriate payroll and other adjustment entries.
• Perform the calculation and application of garnishment deduction orders.
• Prepare supplemental payrolls as needed.
• Manage the calculations and payments for commissions and bonuses.
• With support from the Head of People and other team members, resolve and/or coordinate the resolution or escalation of employee and contractor support issues as needed.
• Partner with Clinical Operations to ensure payments to our therapists are accurate and timely.
• Collaborate with teams across Cartwheel including Business Operations, Care Operations, Clinical Operations, Technology, Finances, Sales, and Customer Success.
  
  

Who You Are

• Embodies our values: Human, Humble, Accountable, Innovative, Resilient
• Has 3-5 years of payroll experience
• Strong preference for experience with healthcare
• Thrives in a world of rapid startup growth
• Achieves quality results quickly and prioritizes outcomes
• Uses data to drive decisions, and has a keen understanding of dashboards and metrics
• In the face of competing priorities, prioritizes and moves forward without getting stuck
• Most importantly, you're ready to support our mission and drive payroll operations at an organization that will help tens of thousands of students and families nationwide get the mental health care they need.
• Understands foundational payroll-related accounting (payroll liabilities, GAAP payroll expense recognition, journal entries for payroll costs, stock-based compensation accounting)
  
  

WHY YOU'LL LOVE CARTWHEEL

Our hope is that Cartwheel will be your best career decision! In addition to tackling one of the biggest challenges of our time, at a company well-positioned to do so, you'll have:

• Competitive compensation between $70,000 - $90,000
• Equity ownership stake in the company
• High-quality health insurance with a $0 monthly premium option for employees
• Dental, Vision, and Employer-Sponsored Life Insurance
• 4 weeks of paid PTO (3 weeks any time 1 week office closure in December)
• Sick Leave Holidays
• 401K with 2% employer match
• In-Person Retreats
• $500 annual educational stipend
• Team-based culture with mission-driven colleagues who will go to bat for you
  
  

Cartwheel is proud to be an equal opportunity employer. We embrace diverse backgrounds and perspectives and an inclusive work environment. We're committed to equal employment opportunity regardless of race, color, religion, ancestry, national origin, gender, sexual orientation, disability status, or veteran status.