Join Cartwheel to help tackle the student mental health crisis.

Kids spend most of their days in the classroom. And teachers and staff, who play a vital role in their development, are often the first to notice when something is off. But with 1 in 5 young people struggling with mental health, schools are getting crushed by a downward spiral in student crises and staff burnout.

With large increases in federal funding for schools and the rise of telehealth, schools are reimagining what mental health support can look like.

Cartwheel is an early-stage startup building technology-enabled mental health services that put schools at the center. We see our role as supporting on-campus counselors, psychologists, and school social workers who see kids every 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 over 200 school districts to provide life-saving mental health services to a diverse population.

We’re scaling quickly – from about 1,500 therapy sessions per week across 12 states today to more than double the number of sessions across 20 states in the next year.

As Cartwheel’s Director of Care Operations, you will oversee Cartwheel’s operations supporting clinicians, schools and families. You will build Cartwheel’s Provider Support and School Support functions and you will oversee Cartwheel’s existing Care Coordination function and team of 20 people that supports students and families. You will design and implement improvements to drive efficiency and to improve the quality of our care operations and you will continuously strive to implement smart automations and responsible AI initiatives.

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

Location: Remote in the U.S., with quarterly in-person offsites

Start date: Summer 2025

Reports to: VP of Operations Victoria Cody

WHAT YOU’LL DO

In your first 30 days, you’ll:

• Get to know your team and learn the ins and outs of Cartwheel’s processes
• Get up to speed on Cartwheel’s growth plans and strategic priorities, and the role of Care Operations in achieving our mission
• Become proficient in the systems we use, including Cartwheel portal, Healthie, Apero, Guru, Talkdesk, Freshservice, Asana, Slack and Google Suite
• Start identifying gaps and process improvement opportunities across existing provider, school and family support functions

Ongoing, you will:

• Build and oversee Cartwheel’s Provider Support function in partnership with Clinical Leadership
• Build and oversee Cartwheel’s School Support function in partnership with School Success leadership
• Oversee Care Coordination function
• Manage our existing team of 20 including care coordinators, senior care coordinators, lead and manager and covering Outreach, Care Ongoing, and External Referrals functions
• Ensure the team is achieving metrics and SLAs and operating at highest quality
• Establish and implement a strategic vision for Care Operations
• Define and measure success for the Care Operations team
• Implement a consistent, centralized platform for managing support needs (e.g., ticketing system like Zendesk)
• Implement innovative solutions to automate issue resolution
• Continually evaluate performance and drive process improvement as we scale nationally
• Oversee all customer support and complaint management workflows, ensuring timely and high quality resolution to all complaints, escalations and task
• Partner with leaders cross-functionally to achieve business priorities, particularly Clinical, School Success, Technology, and People
• Metrics you will be responsible for include:
• Ticket resolution time across provider, school and family support needs
• Volume of tickets or responses closed
• % of tickets or responses automated
• Care coordination metrics, including time to care, conversion to care, and team efficiency metrics (appts scheduled, caseload, etc.)
• This is a starting list and we will be looking to you to help define the success of this function. Additionally, many of the metrics overseen by this function will be highly cross-functional, and we will look to the Director of Care Operations to effectively collaborate cross-functionally to drive performance.

WHO YOU ARE

• Embodies our values: Human, Humble, Accountable, Innovative, Resilient
• Has 7-10+ years of operations experience with a focus on healthcare operations and/or customer support functions
• Strong preference for experience building a customer support function and/or implementing ticketing systems in a high growth technology startup
• Drive to automate workflows and implement responsible AI solutions
• 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
• Seamlessly transitions between strategic thinking and hands-on operations
• Most importantly, you're ready to support our mission and drive core care operations functions that will help tens of thousands of students and families nationwide get the mental health care they need

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 $130,000 - $160,000
• 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
• Flexible PTO + 1 week office closure in December
• Sick Leave + Holidays
• 401K with up to 2% employer match
• $500 annual educational stipend
• Team-based culture with mission-driven colleagues who will go to bat for you
• In-person retreats

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.