Controller

Cartwheel is seeking its first Controller to establish a modern, scalable accounting function to support rapid growth. This role involves building core processes, leading ERP selection and implementation, and creating robust financial infrastructure for audits and fundraising. Reporting to the Head of Finance, the Controller will be a strategic partner across various teams, ensuring high-quality mental health support for students nationwide.

Must Have

• Own core accounting processes including month-end close, reconciliations, controls, and reporting
• Design scalable accounting policies and workflows
• Lead the transition from outsourced to in-house accounting
• Evaluate and select a modern ERP system (NetSuite, Intacct, Rillit, etc.)
• Own ERP configuration, chart of accounts design, integrations, and process buildout
• Establish audit-ready financial infrastructure
• Lead GAAP-compliant reporting and technical accounting decision-making
• Prepare Cartwheel for external audits
• Manage documentation, controls, and alignment with auditors and internal teams
• Hire and mentor a Staff Accountant
• Partner with BizOps and Data on financial reporting and operational metrics
• Collaborate with RCM and Health Plan Ops on payer dynamics and revenue integrity
• Support leadership with budgeting, forecasting, and board reporting
• Strong GAAP foundation and experience leading/supporting external audits
• Primary role in evaluating, selecting, and implementing an ERP system
• Experience building or significantly scaling accounting processes and workflows
• Ability to connect accounting operations to business outcomes and prioritize effectively
• Clear communication with non-finance partners, translating complex financial topics
• Experience hiring, managing, or mentoring accounting talent
• Ability to thrive in early-stage, ambiguous environments

Perks & Benefits

• Mission-oriented and inclusive colleagues
• Competitive compensation
• Meaningful equity ownership stake
• 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

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 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.

ABOUT THE ROLE

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.

Reporting to our Head 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

Location: Remote

WHAT YOU'LL DO

• 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 have led or meaningfully supported external audits, ensuring the company is prepared, organized, and accurate.
• You’ve played a primary role in evaluating, selecting, and implementing an ERP system, and you understand how to design scalable financial infrastructure.
• You’ve built or significantly scaled accounting processes and workflows, bringing a builder’s mindset to creating structure where none exists.
• 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.
• You are passionate about helping kids with behavioral health needs.

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 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

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