Controller

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. 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.

Responsibilities

• 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, Rillet, 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
• 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

Requirements

• 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

Qualifications

• Master’s degree in Accounting, Finance, or related field
• CPA certification preferred
• 5+ years of experience in accounting, finance, or a related field
• Experience in healthcare or payer-heavy environments (behavioral health, Medicaid, fee-for-service, or similar)
• Experience with ERP systems (NetSuite, Intacct, Rillet, etc.)
• Experience with GAAP compliance and financial reporting
• Experience with technical accounting and audit readiness

Skills

• Strong GAAP foundation
• Curiosity about modern tools/automation (including AI)
• Experience in healthcare or payer-heavy environments
• Experience with ERP systems
• Experience with GAAP compliance and financial reporting
• Experience with technical accounting and audit readiness

Benefits

• 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 provided

Pay

$200k cash OTE plus competitive equity package

Schedule

Remote