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.

ABOUT THE ROLE

As an IT Associate at Cartwheel you’ll be part of our technical backbone supporting a growing network of clinical professionals and internal teams as we transform student mental healthcare. This role's mission is to ensure Cartwheelers have seamless, secure access to our technology while providing support to use it. In addition to technical support IT Associates manage accounts and devices for our remote user-base spread across the US. They also handle on-boarding tasks for new hires and develop documentation for systems they administer. You’ll be joining a team of IT professionals focused on building scalable solutions as we continue to grow. Growth opportunities in this position include moving into a more senior support role or one with more engineering focus. At Cartwheel, we fundamentally believe that reliable, user-friendly technology is essential to delivering optimal mental healthcare to the students and families we serve.

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

Location: Remote, based in the United States

Start date: November 2025

WHAT YOU'LL DO

Support Cartwheel Users

• Provide exemplary technical support for all Cartwheel users through our service desk while meeting SLAs
• Build documentation across IT responsibilities toward powering self-service solutions
• Manage on-boarding tasks and training for new hires, including assignment of systems and devices
• Participate in on-call support

Manage Systems and Endpoints

• Management of user accounts across our systems, including use of Okta as a centralized identity provider
• Use automation to streamline user lifecycle tasks
• Manage MacOS endpoint devices through MDM systems
• Maintain an inventory of available devices

Collaborate on Technical Initiatives

• Work closely with team members to implement new IT services
• Take on responsibilities in quarterly projects
• Collaborate with other teams to improve our existing services

WHO YOU ARE

Must have...

• Passion for our mission to tackle the youth mental health crisis and improve outcomes for students and families
• 1 - 3 years of IT support experience preferably in startups, healthcare, or related sectors
• Solution-oriented mindset able to unblock user issues without losing sight of root causes to address afterwards
• Proficiency managing user accounts both across different SaaS services and using an Identity Provider (such as Okta or Google Workspace)
• Proficiency with MacOS endpoints troubleshooting devices and managing through device managers (such as Jamf or Rippling)
• Problem solving skills with strong troubleshooting abilities and a knack for cross-functional collaboration
• Communication abilities to translate complex technical concepts into straightforward language and detailed documentation

Extra credit...

• Healthcare, mental health, or education technology experience with understanding of regulatory requirements and user sensitivity
• Startup experience with ability to work effectively in fast-paced, evolving environments
• Experience supporting part-time users

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:

• Mission-oriented and inclusive colleagues who will go to bat for you
• Competitive compensation between $60,000 - $80,000
• Generous PPO medical, vision, and dental coverage
• Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
• Paid parental leave
• 401K with employer match
• Meaningful equity ownership stake in Cartwheel
• Flexible and remote role with regular in-person retreats
• Annual learning stipend
• Macbook

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 opportunities regardless of race, color, religion, ancestry, national origin, gender, sexual orientation, disability status, or veteran status.

We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization.

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.

We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization