Head of IT at Cartwheel

At Cartwheel, we are addressing the student mental health crisis by placing schools at the heart of our care model. We collaborate directly with school staff to ensure earlier intervention, better engagement for families, and seamless coordination for students. We are backed by prominent investors like Menlo Ventures and General Catalyst, and we are looking for passionate individuals to help us make a lasting impact on millions of students. If you want to build a career where technology directly improves lives, we invite you to join our mission-driven team.

About the Role

We are seeking a Head of IT to join us in a full-time capacity. This is an executive-level role where you will design and implement a modern IT strategy for our rapidly growing organization. You will report directly to the CTO and oversee the hardware, software, security, and budgeting needs for our team. As we prepare to triple in size by the end of 2025, you will play a vital role in ensuring our technology infrastructure supports our commitment to delivering high-quality mental healthcare in the education and healthcare sectors.

Key Responsibilities

• Develop and execute a comprehensive IT strategy that aligns with our company goals and supports our scaling efforts.
• Manage our IT infrastructure, security protocols, and application stack to ensure reliable operations for our clinicians, staff, and partners.
• Collaborate with senior leadership to present technology proposals, manage budgets, and ensure our systems meet rigorous industry standards.

Requirements

We are looking for a leader with at least 10 years of experience in IT management, particularly within high-growth environments. You should have a deep understanding of IT infrastructure and security, with specific expertise in Google Workspace. We value candidates who possess an owner-mindset and a data-driven approach to problem-solving. While not required, a degree in Computer Science or Information Technology, as well as experience in the healthcare or education technology sectors, is highly beneficial. You must be an excellent communicator who can translate complex technical concepts into clear business value for diverse stakeholders.

Location

This position is fully remote and is open to candidates based anywhere in the United States.

Compensation and Benefits

We offer a competitive salary range of $140,000 to $190,000. In addition to your salary, you will receive the following benefits:

• Equity compensation to ensure you have a stake in our success.
• Comprehensive medical, dental, and vision insurance.
• Employer-sponsored life insurance.
• Generous paid time off, including sick leave and company holidays.
• 401k retirement plan with employer matching.
• The flexibility of a remote work environment.