Cartwheel

Role Description 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. Qualifications - 5+ years of experience as a Customer Success Manager implementing and supporting education, education technology, or school-based mental health programs. - Located in Louisiana, Mississippi, or Arkansas (or a neighboring state). - 2+ years of experience working in or around K-12 school systems, such as in a school-based clinician, administrator, teacher, vendor, or business partner. - Commitment to serving communities traditionally overlooked in the healthcare setting – uninsured and underinsured families, youth in foster care, English learners, etc. - Passion for our mission to tackle the youth mental health crisis! Requirements - Active license to deliver clinical care (LCSW, LICSW, LMHC, LCPC, PhD/PsyD) in the South (extra credit). - Clinical experience in the outpatient setting, with comfort managing clinical complexity and safety/risk (extra credit). - Experience working with immigrant populations, rural communities, and/or military families (extra credit). - Experience supporting state-wide initiatives or contracts (extra credit). Benefits - Competitive cash compensation between $95,000 to $115,000 plus 10% variable compensation. - 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 2% employer match. - Team-based culture with mission-driven colleagues who will go to bat for you.

• Provide excellent care, including mental health assessments and teletherapy, to PreK-12 students and school staff • Participate in case discussions with other Cartwheel team members • Support students and families with transition to community care providers • Build collaborative, trusted, and lasting relationships with school leadership, staff, students, and families • If qualified and interested, provide clinical supervision to other care team members

• Provide excellent care, including mental health assessments and teletherapy, to PreK-12 students and school staff in Cartwheel’s partner school districts • Participate in case discussions with other Cartwheel team members • Support students and families with transition to community care providers • Build collaborative, trusted, and lasting relationships with school leadership, staff, students, and families • Meet regularly with school staff to discuss student mental health needs and develop strategies to improve school services • If qualified and interested, provide clinical supervision to other care team members

• Provide excellent care, including mental health assessments and teletherapy, to PreK-12 students and school staff in Cartwheel’s partner school districts (typically 2-4 months per student with extension based on clinical need and clinician’s judgment) • Participate in case discussions with other Cartwheel team members • Support students and families with transition to community care providers • Build collaborative, trusted, and lasting relationships with school leadership, staff, students, and families. Meet regularly with school staff to discuss student mental health needs and develop strategies to improve school services. • If qualified and interested, provide clinical supervision to other care team members

• Provide excellent care, including mental health assessments and teletherapy, to PreK-12 students and school staff in Cartwheel’s partner school districts. • Participate in case discussions with other Cartwheel team members. • Support students and families with transition to community care providers. • Build collaborative, trusted, and lasting relationships with school leadership, staff, students, and families. • If qualified and interested, provide clinical supervision to other care team members.

Role Description 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. As our Marketing Manager, you'll own the marketing engine that keeps Cartwheel's district partners engaged, activated, and renewing. You sit at the intersection of marketing and customer success — building the playbooks, communications, and proof points that make our partners feel supported from day one through renewal and beyond. Right now, Cartwheel is scaling and this hire will be essential to our growth. You'll report to the Head of Marketing and work hand-in-hand with our Customer Success team. This role is right for someone who thinks in systems, writes with clarity across audiences, and gets energy from seeing partners succeed — not just from launching campaigns. Role type: Salaried, full-time Salary: $90,000 - $115,000 + meaningful equity Location: Remote Start Date: Summer 2026 Qualifications - 4–6+ years of marketing experience, ideally in B2B, edtech, healthtech, or a mission-driven company serving multiple buying groups - Proven ability to manage multi-audience communications: you know how to write for a school counselor, a family, and a district administrator and understand why those messages are different - Strong project management instincts: you can run 10 things at once, know what to escalate, and consistently meet deadlines - Experience building and executing lifecycle or retention marketing programs, not just one-off campaigns - Comfort with marketing operations tooling (HubSpot experience a plus) and performance tracking - A bias toward documentation, reporting, and systems: you build things that makes it easy for other people to use - Can own projects end-to-end from writing, producing, and launching Requirements - Preferred experience marketing to K-12 school districts or working within a school-adjacent organization - Familiarity with CSM or customer success workflows - Experience with Asana, Salesforce, Figma, Claude Benefits - Competitive compensation between $90,000 to $115,000 - 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 employer match - Annual educational stipend - Team-based culture with mission-driven colleagues who will go to bat for you

Role Description 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. Since our founding in 2022, we have grown to serve more than fifty school districts across six states, providing care to thousands of students and families. Cartwheel processes a high and growing volume of behavioral health claims across three revenue streams — school district partners, health plans, and members. Without dedicated support, denial and rejection recovery opportunities go unworked and result in preventable revenue loss. This role exists to close that gap. As our Senior Revenue Cycle Specialist, you'll own the workflows that directly protect Cartwheel's bottom line: - Investigating and resolving denials and rejections - Submitting corrected claims and appeals - Managing aging AR - Keeping payer follow-up moving as claim volume grows You'll also serve as the internal expert on billing compliance and payer requirements across all three revenue streams. This role is right for a senior behavioral health billing professional who sees a significant denial and rejection backlog as an opportunity — someone who digs into root causes, builds the systems to prevent recurrence, and wants to scale an RCM operation, not just maintain one. Qualifications - 3+ years of experience as a Billing Specialist, Accounts Receivable Specialist, Payment Coordinator, Revenue Cycle Specialist, or similar role required. - 1+ years of behavioral health billing experience. - Deep expertise in denials management, appeals, corrected claims, and AR follow-up. - Strong working knowledge of healthcare billing regulations, payer requirements, and compliance standards. - Proven ability to independently identify billing issues, investigate root causes, and implement fixes — not just escalate. - Experience with payment posting, cash reconciliation, and resolving complex payment discrepancies for members. Requirements - Experience with Apero and/or Healthie EMR (preferred). - Massachusetts CANS experience (preferred). Benefits - 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.

• Own clinical quality strategy for a rapidly scaling network spanning 20+ states, 400+ clinicians, and multiple care models. • Design and operationalize frameworks for performance monitoring, documentation standards, and audit readiness that are built to scale — not patched as the organization grows. • Translate regulatory requirements into practical workflows. • Present quality trends, risk signals, and improvement recommendations to the extended leadership team alongside peers in Clinical, Operations, and Product. • Inform board-level reporting on clinical risk and compliance posture. • Define what effective, evidenced based clinical supervision looks like at Cartwheel and build the systems to measure and develop it. • Own HIPAA compliance, incident management, complaint and grievance workflows, and payer audit readiness across all operating jurisdictions. • Build clinical compliance policy infrastructure that anticipates growth rather than reacts to it. • Set the performance standard for Cartwheel's clinician network — not just identify when it's missed. • Lead and develop a team that grows with the organization.

Role Description 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. - 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. Qualifications - 5+ years building clinical quality infrastructure in behavioral health — not inheriting or maintaining, but creating - Designed clinical supervision competency frameworks in distributed or multi-site settings - Deep working knowledge of HIPAA, multi-state telehealth regulations, and behavioral health licensing requirements across a large, active state footprint - Experience owning external regulatory relationships — payers, auditors, or state agencies - Clinical licensure (LCSW, LPC, or equivalent) strongly preferred - Approaches quality infrastructure with an innovation and automation mindset — actively leverages AI and technology to build monitoring, reporting, and compliance systems that scale without scaling headcount - Operates at the strategic level: you see where quality risks are heading before they arrive and position the organization accordingly Requirements - Own clinical quality strategy for a rapidly scaling network spanning 20+ states, 400+ clinicians, and multiple care models. - Design and operationalize frameworks for performance monitoring, documentation standards, and audit readiness that are built to scale. - Translate regulatory requirements into practical workflows. - Present quality trends, risk signals, and improvement recommendations to the extended leadership team alongside peers in Clinical, Operations, and Product. - Inform board-level reporting on clinical risk and compliance posture. - Define what effective, evidenced based clinical supervision looks like at Cartwheel and build the systems to measure and develop it. - Own HIPAA compliance, incident management, complaint and grievance workflows, and payer audit readiness across all operating jurisdictions. - Build clinical compliance policy infrastructure that anticipates growth rather than reacts to it. - Set the performance standard for Cartwheel's clinician network. - Partner with Clinical Managers and Provider Network Operations to design re-education pathways and escalation criteria. - Lead and develop a team that grows with the organization. - Shape how quality is understood and practiced across clinical, operations, product, school-facing, and support functions. - Serve as the internal authority consulted early on high-stakes decisions. Benefits - Mission-oriented and inclusive colleagues who will go to bat for you - Competitive compensation - Generous PPO medical, vision, and dental/ortho coverage - Life Insurance - Generous paid time off, including company closure from Christmas-New Years (12/25-1/1) - Paid holidays and sick leave - Paid parental leave - 401K with employer match - Meaningful equity ownership stake in Cartwheel - Flexible and remote role with regular in-person retreats - Annual learning stipend - Laptop

• Conduct structured analysis of denial and rejection data to identify root causes, payer patterns, and filing limit exposure • Move beyond rework — trace denial and rejection spikes to upstream workflow, documentation, or submission failures and drive fixes at the source • Build and maintain AR aging trend tracking and recoverable revenue opportunity analysis • Execute claim corrections, resubmissions, and payer follow-up as a hands-on operational contributor • Build and maintain operational dashboards (Looker preferred) that give RCM leadership real-time visibility into denial volume, payer performance, and AR trends • Produce clear, prioritized findings from claim-level data using pivot tables, formulas, and BI tooling • Design reporting outputs so findings are actionable and accessible to non-billing stakeholders — not just data-literate audiences • Translate billing logic, payer-specific rules, and denial patterns into written, maintainable SOPs • Build operational workflow guides prioritized by highest-volume and highest-denial-rate categories first • Ensure documentation is usable by team members without direct guidance, so operational knowledge scales beyond any one person • Partner with clinical teams to identify upstream documentation or workflow gaps contributing to denials and rejections • Validate billing logic and payer requirements in collaboration with RCM leadership • Communicate findings and recommendations in plain language to non-billing stakeholders including clinical and operations partners • Support training and internal knowledge base development as the operational RCM subject matter resource