Head of IT

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

As the Head of IT at Cartwheel you have the unique opportunity to design and implement a modern approach to how hardware and software are managed in a hypergrowth company. This role is particularly exciting, because it serves industries that historically haven’t prioritized user experience – healthcare and education. In this role, you will report directly to the CTO and lead your team to support the hardware, software, security, and budgeting needs of a 200-person organization that will triple in size by the end of 2025. At Cartwheel, we fundamentally believe that technology is a critical part of delivering optimal mental healthcare to the student population we serve. 

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

Location: Remote, based in the United States

Start date: March/April 2025 

WHAT YOU’LL DO

Strategic IT Leadership:

• Create and execute an IT strategy that supports the company's overall goals.
• Lead significant IT initiatives, from the development to the rollout of new systems and services.
• Regularly evaluate current systems to find areas for improvement, innovation, and growth potential.

Operational Oversight:

• Supervise IT infrastructure, applications, and security to ensure smooth, reliable operations.
• Define and report on clear objectives for the team, offering support and direction to ensure performance and success.
• Provide IT support to various groups including clinicians, employees, counselors, families, and students.

Executive Collaboration:

• Work closely with senior leadership to communicate IT goals and initiatives.
• Prepare and present technology proposals, business plans, and budgets to management and stakeholders.

Security & Compliance:

• Oversee IT governance and risk management practices to protect company data and assets.
• Implement best practices for system configuration, security, and maintenance to meet industry and regulatory standards.

Vendor Management and Relationship Building:

• Cultivate strong partnerships with external vendors and tech partners to ensure alignment with company needs.
• Negotiate contracts, SLAs, and pricing to maximize value and ensure service quality.
• Stay updated on vendor roadmaps and industry developments to proactively manage potential changes.

WHO YOU ARE 

Must have…

• Passion for our mission to tackle the youth mental health crisis
• 10+ years of relevant IT management experience
• Proven track record of planning and delivering successful IT projects 
• Deep understanding of IT infrastructure, security, and best practices, especially in a Google Workspace environment
• Strong affinity toward data-driven thinking by measuring and iterating on processes.
• An owner-mindset that drives you to improve the company even when it means stepping outside of a traditional IT role
• Experience with high growth companies and corresponding IT related challenges 
• Strong analytical and problem-solving skills. 
• Excellent communication and collaboration skills. 
• Customer-centric focus with ability to translate technical solutions to business value
• A curiosity driven by first principles thinking in service of reimagining how technology can improve healthcare and education
• At times, work efficiently under high levels of pressure and demanding timelines.

Extra credit…

• Possess a degree in Information Technology, Computer Science or a related field
• Experience in healthcare and/or Ed. Tech
• Experience working in early stage technology startups

Skills…

• Project Management: Excellent project management skills with the ability to coordinate across many stakeholders and prioritize tasks
• Technically Savvy: Fluency in modern tech stacks (Google Workspace, Slack, etc.) with an ability to quickly learn new technologies. 
• Relationship Builder: Experience with building relationships across diverse stakeholders and influence without authority
• Strong Communicator: Superb written and verbal communication skills 
• Organized thinker: Instinctively structures problems into logical components

Please apply even if you don't meet all of the criteria. If your past experience doesn’t perfectly match the job description, but you bring other relevant experience or skills, we’d still love to hear from you. You may be a great fit!

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 $140,000 - $190,000
• 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 up to 2% employer match
• $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.