Cartwheel

Recruitment

• Own the operational side of our hiring engine — you’ll run the day-to-day flow of interviews, candidates, and ATS data so the recruiter can focus on strategy, stakeholder alignment, and closing.
• Take point on simpler roles (e.g., coordinators, support roles, select clinical support roles) by handling posting, screening to a clear rubric, coordination, and offer logistics, while the recruiter owns compensation, stakeholder management, and final decisions.
• Act as more than a scheduler by anticipating conflicts, designing interview flows that make sense, and keeping everyone prepared, in the loop, and on the same page.
• Have the opportunity to flex your support based on volume — some periods may lean more corporate and others more clinical, and you’ll shift where your help has the greatest impact.
• Drive process, not strategy — maintain clean, accurate Greenhouse pipelines, keep interviews moving, and run tight debriefs without owning high-level hiring strategy or headcount planning.
• Bring an operational mindset by spotting patterns, flagging risks early, and identifying small but impactful process improvements that make our hiring engine more scalable and predictable.

Talent Acquisition Specialist

Controller

• 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
• 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.
• 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 Staff Accountant shortly after onboarding.
• Provide mentorship, clarity, and development as the team grows.
• 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.

Therapist

• 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

Mental Health Therapist, Contractor

Product Designer

• Lead the design process for major features, from ideation through implementation, incorporating feedback from diverse stakeholders, including the executive team.
• Quickly iterate and prototype several concepts to validate product direction
• Facilitate collaboration sessions with product managers and engineers to create optimal user flows
• Partner with data teams to develop visualizations that help school staff monitor student outcomes
• Partner with operations and customer success teams to streamline access to care for students and families
• Conduct user behavior research and establish a data-driven design practice to inform feature development
• Deliver detailed specifications and assets to engineering.
• Maintain and enhance our design system to improve the efficiency and quality in feature development
• Work side-by-side with QA teams to ensure final builds align with designs

Senior Product Designer

Operations

• Partner with the Director of Health Plan Operations around group contracting strategy
• Lead delegated credentialing efforts for provider enrollment
• Build operational infrastructure for psychiatrist and nurse practitioner licensing
• Drive strategic projects for Health Plan Operations and Revenue Cycle analyzing key workflows

Health Plan Operations Manager

Marketing

• Design and execute end-to-end lifecycle campaigns in Iterable that move families from referral through assessment, enrollment, and active care utilization
• Build automated trigger-based campaigns that respond to user behaviors, drop-off points, and engagement signals throughout the care journey
• Optimize conversion funnels at each stage: referral acceptance, family engagement, initial appointment scheduling, and ongoing session attendance
• Develop segmentation strategies to personalize messaging based on referral source, student needs, family engagement level, and utilization patterns
• A/B test messaging, timing, and channels to continuously improve conversion rates and reduce friction in the care journey
• Create nurture sequences that address common barriers to engagement (stigma, logistics, confusion about services)
• Collaborate with clinical, operations, and product teams to understand drop-off reasons and address them through strategic communications
• Build campaigns to engage and educate referring staff (counselors, teachers, administrators) on Cartwheel services, referral best practices, and student progress
• Create feedback loops that keep referring staff informed about student outcomes and reinforce referral behaviors
• Develop family engagement campaigns that support family self interest form submissions
• Design re-engagement campaigns for families who have disengaged or students who have missed appointments
• Own lifecycle marketing strategy from concept through execution, measurement, and iteration
• Conduct market and customer research to inform messaging, positioning, and campaign strategy
• Develop product marketing materials that clearly communicate Cartwheel's value proposition to families and school staff
• Partner with marketing, operational, and product leadership to align lifecycle campaigns with broader company goals and outcomes
• Build reporting dashboards that track campaign performance, conversion metrics, and impact on utilization KPIs
• Identify and prioritize opportunities to improve the end-to-end experience through marketing interventions

Lifecycle Marketing Manager

Business Operations

• Lead clinical and operational projects including initiatives to improve patient intake and scheduling efficiency
• Lead cross-functional strategic initiatives as the business demands
• Support teams across Cartwheel, in particular our Clinical Care team, in evaluating needs, running analyses, and implementing new initiatives
• Flex into other roles internally as demanded by the business

Business Operations Associate

Onboarding Specialist

• Provide part time clinical and operational support to help execute the onboarding and training process for new clinical hires.
• Report to the Clinical Onboarding & Training Lead.
• Ensure that every new Cartwheel clinician is ready to deliver high-quality care to the students and families we serve.
• Grade and provide feedback for onboarding skills assessments.
• Respond to emails and Slack messages from new clinical hires, and escalate concerns as needed.
• Meet with new clinical hires to provide navigational support and answer questions throughout onboarding process.
• Collaborate with stakeholders to audit onboarding content periodically, update materials as needed, and develop new resources.
• Attend meetings to share feedback from new clinical hires and identify gaps/opportunities for improvement.
• Shadow orientation with the future goal of co-leading with People Ops Associate.
• Additional tasks as requested.

Part-Time Clinical Onboarding Specialist

• 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

Mental Health Therapist – Bilingual, Spanish and Portuguese

People Operations

• Serve as the strategic thought partner to leaders across the organization, enabling teams to operate at top of license
• Design a lightweight performance review framework and support the next cycle end to end (timeline, communications, calibration, decisions)
• Build a consistent performance management framework and workflow; coach managers and maintain documentation
• Develop and maintain Role & Responsibility documents with measurable outcomes for all corporate roles
• Equip managers with toolkit and trainings on feedback, goals and metrics, effective 1:1s, and HRBP escalation; track adoption and impact
• Support employee-led ERGs with cadence and governance, ensuring safe escalation and follow-through
• Co-lead updates to the employee handbook and key policies with People Ops, prioritize sections for business and compliance
• Extra Credit: Build scalable processes for 1099 clinical network

People Business Partner

• Provide excellent care, including mental health assessments and skills-based teletherapy, to elementary, middle and high school students in Cartwheel’s partner school districts (typically 2-4 months per student with possible extension up to 6 months)
• Collaborate closely with referring school counselors and other relevant providers at start of treatment and over the course of a student’s care journey (including through regular phone calls, emails, and virtual meetings)
• Build trusted relationships with school staff and families to support a student’s mental health needs, school engagement and engagement with school-based services, as applicable
• Provide regular psychoeducation and support to parents and caregivers to enhance a student’s mental health needs and individual therapy work
• Collaborate with Cartwheel MDs/NPs on treatment planning, care delivery and transition planning over a student’s care journey
• Partner with the External Referrals team to support the identification of referrals to community mental health and primary care providers
• Have the opportunity to participate in case consultations and discussions with other Cartwheel team members
• Help to further build Cartwheel’s clinical programming and wonderful Care Team

Mental Health Therapist

Product Manager

• Own the #1 driver of Cartwheel’s value for existing school district customers, directly impacting mental health access for hundreds of thousands of students
• Spend significant time with school counselors and administrators, translating their needs into experiments and valuable features
• Focus on increasing contract utilization by identifying friction points, running rapid experiments, and shipping solutions that help students and families successfully engage in care
• Span the school district journey from initial sale through renewal and the patient journey from initial referral to care completion
• Develop the product vision for maximizing the value of Cartwheel for our school district customers
• Engage in continuous discovery with school staff, students/families, and Cartwheel’s care team
• Map out opportunities, generate solutions, name assumptions, design experiments to test those assumptions, and iterate to refine solutions
• Work cross-functionally to align stakeholders, translate treatment protocols into scalable product experiences, incorporate school district strategic goals into our product roadmap, and run experiments with engineering and data
• Evaluate and experiment with novel AI use cases (e.g., between-session student engagement, referral identification, personalized collaboration with schools)

Senior Product Manager, Growth and Engagement

Financial Planning and Analysis

• Build the Strategic Finance function at Cartwheel from the ground up
• Improve and maintain Cartwheel’s financial/operating forecast, in close partnership with the COO, CEO, and leadership team. This includes scenario planning to drive investment decisions.
• Monitor and report on key financial metrics aligned to our OKRs to the Senior Leadership Team and Board of Directors.
• Partner with departments to strategically manage their budgets and analyze variance
• Collaborate with outsourced accounting partners to ensure timely and accurate monthly close; work toward insourcing accounting function, including hiring a controller in early 2026
• Partner cross-functionally to drive effective decision-making across the business. You will be working most closely with the People and Operations teams but will also engage with Sales, Customer Success, R&D, and others as well. This includes creating important analyses to inform key decisions (e.g., school district-level profitability, state-level contribution margin).

Director, Strategic Finance

Engineering Manager

• Create and execute engineering strategies that align with company objectives and drive measurable business outcomes.
• Lead complex technical initiatives from conception through delivery, ensuring alignment with product roadmaps and organizational goals.
• Regularly evaluate team performance, technical debt, and system architecture to identify opportunities for improvement and innovation.
• Translate complex technical concepts into business-focused recommendations and strategic planning inputs.
• Oversee engineering operations, code quality, and delivery processes to ensure reliable, scalable product development.
• Define and track clear performance objectives for engineering teams, providing guidance and support to maximize productivity and impact.
• Establish and maintain software quality standards, development best practices, and technical documentation across projects.
• Build and execute comprehensive recruiting, retention, and talent development strategies to scale engineering capabilities.
• Foster an inclusive, high-performance culture that promotes continuous learning and career growth.
• Implement effective team processes, communication frameworks, and feedback mechanisms to optimize team dynamics and individual development.
• Cultivate strong collaborative relationships with product, design, and business stakeholders to ensure seamless project execution.
• Navigate complex dependencies and requirements to deliver solutions that meet both technical and business specifications.
• Drive alignment across departments on technical decisions, project priorities, and resource allocation to maximize organizational effectiveness.
• Report directly to the CTO and lead a team supporting strategic planning and software development across a 25-person R&D organization.