Controller

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 A Street Ventures, Menlo Ventures, Reach Capital, General Catalyst, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

We’re hiring our first Controller to build a modern, scalable accounting function that will support Cartwheel’s rapid growth. As our accounting leader, you’ll build core processes from scratch, lead our ERP selection and implementation, and create the financial infrastructure we’ll rely on for audits, fundraising, and multi-state expansion. This is a true builder role — not inheriting a fully built function, but designing the systems, controls, and processes that will scale with the company.

Reporting to our VP of Finance, you’ll be a key strategic partner to teams across the company—including BizOps, Data, RCM, and Operations—as we bring high-quality mental health support to students everywhere.

Role type: W2, Full-Time, Salaried position
Salary range: 200k cash OTE plus competitive equity package
Location: Remote

• Build and Lead the Accounting Function
  • Own core processes including month-end close, reconciliations, controls, and reporting.
  • Design scalable accounting policies and workflows.
  • Lead the transition from outsourced accounting function to fully in-house
• Lead ERP Selection and Implementation
  • Evaluate and select a modern ERP (NetSuite, Intacct, Rillit, etc.) with cross-functional partners.
  • Own configuration, chart of accounts design, integrations, and process buildout.
  • Establish a strong, audit-ready financial infrastructure from day one.
• Own Technical Accounting and Audit Readiness
  • Lead GAAP-compliant reporting and technical accounting decision-making.
  • Prepare Cartwheel for its first (or subsequent) external audit.
  • Manage documentation, controls, and alignment with auditors and internal teams
• Hire a Small Team
  • Hire a Staff Accountant shortly after onboarding.
  • Provide mentorship, clarity, and development as the team grows.
• Partner Across the Business
  • Work with BizOps and Data to connect financial reporting to operational metrics (RCM, state P&L, revenue quality).
  • Collaborate with RCM and Health Plan Ops on payer dynamics, collections, and revenue integrity.
  • Support leadership with budgeting, forecasting, and board reporting.

WHO YOU ARE

• You have a strong GAAP foundation and you are curious about modern tools/automation (including AI) and are excited about leveraging technology to make accounting more efficient and insightful.
• You have owned or led an external audit end-to-end (planning, PBC coordination, auditor management, remediation), and are confident operating in audit-ready environments.
• You’ve played a meaningful role in ERP selection and implementation — including requirements gathering, system configuration, chart of accounts design, testing, and post–go-live operations.
• You’ve built or significantly scaled accounting processes and workflows, bringing a builder’s mindset to creating structure where none exists.
• You have experience in healthcare or payer-heavy environments (behavioral health, Medicaid, fee-for-service, or similar), and understand the nuances of bad debt, reimbursement, and revenue cycle complexity.
• You connect day-to-day accounting operations to broader business outcomes and know how to prioritize effectively in a fast-paced environment.
• You communicate clearly with non-finance partners, translating complex financial topics into accessible insights and building trust across teams.
• You’ve hired, managed, or mentored accounting talent and know how to develop people while maintaining a high bar for quality.
• You thrive in early-stage, ambiguous environments, enjoy rolling up your sleeves, and can move work forward without a perfect playbook.

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 and meaningful equity ownership stake in Cartwheel
• Generous PPO medical, vision, dental and ortho coverage
• Unlimited/flexible PTO plus federal holidays
• Paid parental leave
• Life Insurance
• 401K with employer match
• Flexible and remote role with regular in-person retreats
• Annual learning stipend
• Laptop