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. 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

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 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.

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
• Laptop 

Join Cartwheel to help tackle the student mental health crisis as part of its founding Minnesota clinical team. 

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. 

ABOUT THE ROLE

We’re looking for outcomes-oriented and mission-driven therapists who are fluent in Spanish and/or Portuguese to join our amazing and interdisciplinary care team of psychiatrists, therapists, and school health professionals. As a Mental Health Therapist, you'll work directly with school staff, students, and families in our partner school districts to build stronger systems of mental health support.

Role type: This is a 1099 Independent Contractor position

Location: Remote in the U.S.

WHAT YOU’LL DO

• 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

WHO YOU ARE

Must have…

• Fluency in Spanish or Portuguese
• Active independent license (LCMHC, LMFT, LCSW, Psychologist (PhD)) in one or more of the following states: CT, GA, IN, MN, NC, NH, NV, WI
• Master’s degree in Social Work, Psychology, Counseling, Marriage & Family Therapy, or related field
• Experience with CBT, DBT, ACT, solution-focused therapy, and/or motivational interviewing
• At least two years of experience delivering mental health services to children and youth via telehealth. We use Zoom, GSuite (Google Calendar, Gmail, etc.), electronic health record systems, and other collaboration tools.
• Access to reliable, high-speed internet (50 Mbps download, 10 Mbps upload, you can test your internet speed at https://www.speedtest.net/) 
• Excellent organization, communication, and teamwork skills
• Ability to offer hours during and especially after school (e.g., 3-8 pm Mountain Time, Saturdays)
• Ability to provide effective and safe care to children and adults, including ability to manage crisis situations virtually.

Extra Credit…

• 5–12+ years of clinical experience
• Comfort with technology and new systems (Zoom, GSuite, EHRs, collaboration tools)
• Experience with parent guidance
• Qualified to provide clinical supervision
• Active NPI number (Need to apply for your NPI? Visit this link. It takes 2-4 weeks)
• CAQH credentialing set up (Need to apply for CAQH? Visit this link. It takes 3-4 days)
  
  

WHY YOU’LL LOVE CARTWHEEL

At Cartwheel, you’ll have an unmatched provider experience.

• Competitive compensation starting at a $55/hour base hourly rate + up to 5% quarterly Mission Bonus for Master’s-level clinicians, dependent on state licensure, experience, language, etc.
• The Mission Bonus of up to 5% is paid quarterly for serving higher-need populations ( based on the % of students you see who have Medicaid, are uninsured, or speak a non-English language)
• Access to free online accredited continuing education and a CEU stipend
• Clinical Supervision for associate level clinicians
• Administrative support from our experienced, full-time Care Coordinators, and optional access to an AI-enabled medical scribe that saves you hours of documentation time  (this is used and loved by the majority of Cartwheel clinicians!)
• Team-based care with mission-driven colleagues building a truly innovative school-community partnership model
• Opportunities beyond clinical care, including working closely with schools on staff support, workshops, and other programming

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student’s life

ABOUT THE ROLE

We’re looking for team-oriented and mission-driven therapists who believe in the power of collaborative care to join our amazing and interdisciplinary care team of psychiatrists, nurse practitioners, therapists, and school health professionals. As a Mental Health Therapist, you'll work directly with school staff, students, and families in our partner school districts to build stronger systems of mental health support.

Role type: 1099 independent contractor (10-20 hours per week)

Location: 100% remote in the U.S.

Specific needs: Spanish-speaking therapists

Start date: Immediate starts for summer 2026

WHAT YOU’LL DO

• 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

WHO YOU ARE 

Must have…

• Passion for working in close partnership with schools on mental health
• Master’s Degree or higher from an accredited school of Social Work, Psychology, Counseling or Marriage, or Family and Child Counseling.
• Active associate or independent license in Illinois to deliver mental health care (LCSW, LPC, LMFT, or PhD/PsyD, etc.)
• Experience with CBT, DBT, ACT, solution-focused therapy, and/or motivational interviewing
• Experience delivering care via telehealth
• Strong technological skills and learning new systems, including Zoom, GSuite (Google Calendar, Gmail, etc.), electronic health record systems, and other collaboration tools
• Access to a reliable, high-speed internet connection (50 Mbps download, 10 Mbps upload)
  • You can test your internet speed at https://www.speedtest.net/ 
• Excellent organization, communication, and collaboration skills
• Ability to deliver care during our peak hours (Mon-Fri 3-8 pm ET and Sat 8-5) 
• NOTE: As long as you have an active license in the above state, you can live and deliver care from anywhere in the United States

Extra credit…

• Fluency in other languages (e.g., Spanish, Portuguese)
• Active NPI number (Need to apply for your NPI? Visit this link. It takes about 2 to 4-weeks)
• CAQH credentialing set up (Need to apply for CAQH? Visit this link. It takes about 3 to 4-days)
• Experience working in a shorter-term model of care delivery (e.g., 2 weeks to 6 months)
• Experience with parent guidance
• Excitement to join an early stage start-up and help bring Cartwheel to more students and school districts

The above is a summary of the role, not an exhaustive list. If you think that you have most of the above but not everything, please apply. We'd love to hear from you.

WHY YOU’LL LOVE CARTWHEEL

At Cartwheel, you’ll have an unmatched provider experience.

• Flexible and 100% remote role (10-20 hrs/week)
• Competitive compensation ($45-85/hour base hourly rate for Master’s-level clinicians, dependent on licensure, experience, language, etc.)
• Team-based care model with mission-driven colleagues
• Administrative support from our experienced, full-time Care Coordinators so you can focus on delivering care
• Opportunities beyond clinical care, including working closely with schools on staff support, workshops, and other programming

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student’s life

ABOUT THE ROLE

We’re looking for team-oriented and mission-driven therapists who believe in the power of collaborative care to join our amazing and interdisciplinary care team of psychiatrists, nurse practitioners, therapists, and school health professionals. As a Mental Health Therapist, you'll work directly with school staff, students, and families in our partner school districts to build stronger systems of mental health support.

Role type: 1099 independent contractor (10-20 hours per week)

Location: 100% remote

Start date: Immediate starts for summer 2026

WHAT YOU’LL DO

• 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

WHO YOU ARE 

Must have…

• Passion for working in close partnership with schools on mental health
• Master’s Degree or higher from an accredited school of Social Work, Psychology, Counseling or Marriage, or Family and Child Counseling.
• Active license in Wisconsin to deliver mental health care independently without supervision (LCSW, LPC, LMFT, or PhD/PsyD, etc.)
• Experience with CBT, DBT, ACT, solution-focused therapy, and/or motivational interviewing
• Experience delivering care via telehealth
• Strong technological skills and learning new systems, including Zoom, GSuite (Google Calendar, Gmail, etc.), electronic health record systems, and other collaboration tools
• Access to a reliable, high-speed internet connection (50 Mbps download, 10 Mbps upload)
  • You can test your internet speed at https://www.speedtest.net/ 
• Excellent organization, communication, and collaboration skills
• Ability to deliver care during our peak hours (Mon-Fri 3-8 pm ET and Sat 8-5) 
• NOTE: As long as you have an active license in the above state, you can live and deliver care from anywhere in the United States

Extra credit…

• Fluency in other languages (e.g., Spanish, Portuguese)
• Experience working in a shorter-term model of care delivery (e.g., 2 weeks to 6 months)
• Experience with parent guidance
• Active NPI number (Need to apply for your NPI? Visit this link. It takes about 2 to 4-weeks)
• CAQH credentialing set up (Need to apply for CAQH? Visit this link. It takes about 3 to 4-days)
• Excitement to join an early stage start-up and help bring Cartwheel to more students and school districts

The above is a summary of the role, not an exhaustive list. If you think that you have most of the above but not everything, please apply. We'd love to hear from you.

WHY YOU’LL LOVE CARTWHEEL

At Cartwheel, you’ll have an unmatched provider experience.

• Flexible and 100% remote role (10-20 hrs/week)
• Competitive compensation ($45-80/hour base hourly rate for licensed Master’s-level clinicians, dependent on licensure, experience, language, etc.)
• Team-based care model with mission-driven colleagues
• Administrative support from our experienced, full-time Care Coordinators so you can focus on delivering care
• Opportunities beyond clinical care, including working closely with schools on staff support, workshops, and other programming

Join Cartwheel to help tackle the student mental health crisis. 

LOCATION: Remote (US) with ability to travel 2x a month including weekly during peak seasons (e.g., legislative session). 

TERRITORY: Preference for South, Great Plains, or Mountain West homebase.

COMPENSATION: Competitive base + variable compensation (% of deals closed) + meaningful equity 

START DATE: May 2026

ABOUT THE ROLE

In 3 years, Cartwheel has grown to serve more than 325 school systems in 16 states, making us the nation's largest mental health provider that collaborates with schools. We're now building the government partnerships function to match that scale — securing the statewide contracts and legislative appropriations that let us serve entire state school systems, not one district at a time.

This is a new function. There's no inherited pipeline, no established playbook, and no hand-holding. What exists is a proven model in Georgia and Arizona, a product that works, and a mission that resonates with state officials across the political spectrum.

You'll own a portfolio of 5–10 states across the South, Great Plains, and Mountain West — and your job is to build the government affairs infrastructure that turns those states into Cartwheel markets.

WHAT YOU'LL DO

Own strategy and execution for your state portfolio

• Develop state-by-state government affairs strategies — stakeholder maps, legislative calendars, messaging, milestones, and critical path
• Pursue two primary win types: (1) state funding and appropriations that schools use to procure Cartwheel, and (2) Securing direct statewide contracts that make Cartwheel the sole vendor available to districts at no cost
• Example of #1 is Georgia HB68 school mental health grant funding that gives $20,000 to each middle and high school to contract for mental health services
• Example of #2 is our partnership in Arizona with the AZ Department of Education to serve all rural school districts and charter schools
• Track legislative opportunities, RFPs, and policy developments to stay ahead of the curve in your territory

Build and steward relationships with state leaders

• Cultivate trust-based relationships with governors' offices, state legislators, education and health agencies, and key statewide organizations
• Navigate regulatory and political environments to create favorable conditions for Cartwheel — tailoring messaging to each state's context
• Manage external lobbyists in your states with clear objectives, accountability, and measurable deliverables

Drive revenue and operational rigor

• Own the full government sales cycle — from cold relationship to signed contract or secured appropriation
• Maintain pipeline tracking and stakeholder mapping in Salesforce; report weekly to the VP of Government Relations on status and forecast
• Collaborate with Sales, Marketing, Product, and Customer Success teams to ensure Cartwheel delivers the outcomes required to renew and expand statewide contracts year-over-year

WHO YOU ARE

• 7+ years operating at the intersection of government and private sector revenue — government affairs, government sales, or policy roles where your work had a direct commercial outcome
• Demonstrated track record getting government entities to say yes — whether that's a contract, an appropriation, a regulatory approval, or a procurement — and owning that process personally, not as part of a team
• Experience navigating state or local government structures: legislative cycles, agency relationships, executive office dynamics
• Comfortable managing long, ambiguous sales cycles across multiple simultaneous markets
• Experience directing or coordinating external partners (lobbyists, consultants, advocacy orgs) toward specific outcomes
• CRM proficiency; strong written and verbal communicator across stakeholder types
• Based in or willing to commute extensively in South, Great Plains, or Mountain West; able to travel 2x/month plus weekly during peak legislative seasons
• Energized by building from scratch — this role has no inherited infrastructure

Sector experience that would accelerate your ramp:

• State education agencies, K–12 policy, or school district procurement
• Healthcare, behavioral health, or Medicaid/CHIP funding structures
• EdTech or healthcare startups where you sold into or through government

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 benefits
• Meaningful equity ownership stake in Cartwheel
• Generous PPO medical, vision, and dental coverage
• Unlimited/flexible PTO plus federal holidays
• Paid parental leave
• 401K with employer match

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

In 3 years, Cartwheel has grown to serve more than 325 school districts in 16 states, making us the nation’s largest mental health provider that collaborates with K-12 schools. With billions of dollars in new state and federal investments in youth mental health coming in 2026, we are supplementing our district-level sales motion with statewide partnerships with Governor’s offices, education departments, and health agencies.

As the Enterprise Customer Success Manager, you will be Cartwheel's primary point of contact with the state agency, responsible for turning a signed contract into a high-impact, expanding program. That means building the implementation plan, coordinating execution across Cartwheel's internal teams, keeping agency staff informed and confident, and clearing whatever is in the way of delivering exceptional impact. Throughout the contract period, you’ll partner closely with our Government Relations teams, which will own executive and legislative relationships and the contract renewal process.

Role type: W2, Full-Time, Salaried position
Salary range: $143,000 – $187,000 OTE (10% variable pay included) plus competitive equity package
Location: Remote
Target Start: June 2026

WHAT YOU'LL DO

Own the state agency relationship

• Be the primary Cartwheel contact for agency program directors, behavioral health leads, and operational staff — the people responsible for implementing the partnership. 
• Build a deep understanding of agency priorities, constraints, and decision-making so you can navigate complexity and keep things moving
• Develop and maintain a comprehensive contact map across agency implementers, influencers, and financial buyers — and build productive relationships across each layer
• Lead regular agency check-ins covering progress, milestone tracking, and issue resolution
• Navigate agency political dynamics, policy constraints, and interagency complexity
• Develop success stories as implementation matures to support renewal and expansion

Drive implementation

• Build and own the implementation plan for your state(s): What needs to happen, in what order, by when, and who is responsible
• Develop a district prioritization framework: Where to start, how to sequence expansion, how to pace growth against contract timelines
• Own and track the metrics that matter — utilization, district activation, contract milestone attainment — and surface risks early before they become problems
• Coordinate across internal Cartwheel teams to ensure we meet all of our impact goals and milestones. For example:
• Partner with the Government Relations team on renewal readiness and ensure they have an excellent value story to share with executive and legislative buyers
• Ensure district-level sellers and CSMs are effectively onboarding districts
• Coordinate with Operations to clear compliance, credentialing, and regulatory hurdles that slow implementation down

• Engage state-level professional associations (superintendent associations, state education agencies) to support district activation and strengthen Cartwheel's presence

Keep leadership and the team aligned

• Maintain clear, multi-quarter visibility into contract health and district-level risk
• Report out on contract health to Senior Leadership and share insights on how to improve our approach to state implementations, product innovation, or other key insights
• Identify expansion opportunities (new districts, expanded services, adjacent agency relationships) and surface them to Government Relations and internal teams to pursue

WHAT WE’RE LOOKING FOR

Required

• 7–10+ years in customer success, strategic account management, or a closely related post-sale role, with meaningful experience in government or public sector
• You're an exceptional communicator — able to translate operational complexity into clear reporting for agency partners and internal leadership
• You've built trusted relationships with state or government agency staff. Not just executives, but program officers and operational leads
• You've managed complex, multi-stakeholder account plans and can connect the dots between day-to-day execution and long-term contract health
• You understand the revenue implications of implementation decisions and take ownership of retention outcomes
• You can navigate political and bureaucratic dynamics without losing momentum
• You are comfortable interpreting data on your own and communicating insights
• You're highly organized and comfortable building structure in an environment that doesn't have all the answers yet

Preferred

• Experience in K–12 education, healthcare, or direct service businesses
• Familiarity with braided funding models (state contracts, Medicaid, grants, district fees)
• Background working alongside or within Government Relations or public affairs functions
• Experience with state procurement processes and compliance relevant to public sector
• Familiarity with ChurnZero, Gainsight, Salesforce, or HubSpot

Travel

This role requires regular travel — approximately 40% — to support state agency relationships, district engagement, and key implementation milestones, concentrated in your assigned state(s).

Please apply even if you don't meet all of the criteria. If your past experience doesn't perfectly match the job description, but you bring other relevant experience or skills, we'd still love to hear from you. You may be a great fit!

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
• 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 

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 a Finance Associate to own financial reporting, planning, and KPI/OKR visibility across the organization. This is a net-new role — and a real opportunity to build something. Right now, our financial and operational metrics live in different systems, most reporting is backward-looking, and department leaders don't yet have the structured financial partnership they need to make confident decisions.

Reporting to Sam Bilow, VP Finance, you'll consolidate our reporting infrastructure, build forward-looking forecasts, and become a trusted cross-functional partner to leaders across Care Ops, Clinical, Product, Engineering, and beyond. If you thrive in high-rigor, fast-paced environments — think Investment Banking or Big 4 Consulting — and want to apply that edge to growing a company with a mission that matters, this role is for you.

Role type: W2, Full-Time, Salaried position
Salary range: $90,000–$140,000 cash compensation plus competitive equity package

Location: Remote

WHAT YOU'LL DO

Strategic Finance

• Build forward-looking forecasts to support runway planning and board communication
• Identify opportunities to automate and scale financial reporting processes
• Conduct ad-hoc analyses that help leadership make faster, better-informed decisions

Financial Modeling & Reporting

• Maintain and improve Cartwheel's core financial model — P&L, cash burn, scenario modeling
• Own monthly board slide deck, investor reporting, and SLT financial updates
• Maintain and continuously improve KPI dashboards

Budgeting & Planning

• Lead the annual budgeting cycle: templates, department kick-offs, reviews, and final consolidation
• Partner with department heads on budget planning and resource allocation
• Maintain budget vs. actual tracking and variance analysis

WHO YOU ARE

• You have 2–4 years of experience from investment banking, management consulting (MBB, Big 4, or similar), or a high-rigor FP&A role — startup or high-growth experience is a strong plus
• You're fluent in Excel (VLOOKUP, pivot tables, scenario modeling) and comfortable building clean, well-structured financial models from scratch
• You translate financial concepts clearly for non-financial audiences — you know when to simplify and when precision matters. You can build a clean board slide or exec summary from scratch.
• You're self-directed and ownership-oriented: you spot problems, propose solutions, and don't wait to be asked
• You're comfortable operating with incomplete data — you forecast with 80% information and refine from there
• You care about the mission. You understand that finance is in service of student mental health, not the other way around

We set a high bar for this role. If you have a strong consulting or IB foundation and are excited to apply those skills to a high-impact mission, we'd love to hear from you.

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 $90,000 - $140,000
• 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 

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student’s life

ABOUT THE ROLE

We’re looking for team-oriented and mission-driven therapists who believe in the power of collaborative care to join our Provider Network! Express your interest in future openings as we expand into new states and stay updated on webinars, initiatives, and more through our blog. Even if we aren’t currently hiring in your state (you can see where we are hiring on our careers page here), applying now will fast-track your application for future openings. As a Mental Health Therapist, you'll work directly with school staff, students, and families in our partner school districts to build stronger systems of mental health support.

Role type: 1099 independent contractor (10-20 hours per week)

• W2 hourly for providers living in CA or MA, and for non-independent MA licensed therapists

Location: Remote in U.S. 

WHAT YOU’LL DO

• 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

WHO YOU ARE 

Must have…

• Passion for working in close partnership with schools on mental health
• Active license to deliver mental health care (LMHC, LMFT, LICSW, LPC, LCSW, LCPC, PhD/PsyD, etc.)
• Experience with CBT, DBT, ACT, solution-focused therapy, and/or motivational interviewing
• Experience delivering care via telehealth
• Strong technological skills and learning new systems, including Zoom, GSuite (Google Calendar, Gmail, etc.), electronic health record systems, and other collaboration tools
• Access to a reliable, high-speed internet connection (50 Mbps download, 10 Mbps upload)
  • You can test your internet speed at https://www.speedtest.net/ 
• Excellent organization, communication, and collaboration skills
• Ability to offer hours both during and especially after a typical school day (e.g., 3-8 pm and/or Saturdays 8-5) 
• NOTE: As long as you have an active license in an operating state, you can live and deliver care from anywhere in the United States

Extra credit…

• Fluency in other languages (e.g., Spanish, Portuguese, Mandarin)
• Active NPI number (Need to apply for your NPI? Visit this link. It takes about 2 to 4-weeks)
• CAQH credentialing set up (Need to apply for CAQH? Visit this link. It takes about 3 to 4-days)
• Experience working in a shorter-term model of care delivery (e.g., 2 weeks to 6 months)
• Experience with parent guidance
• Excitement to join an early stage start-up and help bring Cartwheel to more students and school districts

The above is a summary of the role, not an exhaustive list. If you think that you have most of the above but not everything, please apply. We'd love to hear from you.

WHY YOU’LL LOVE CARTWHEEL

At Cartwheel, you’ll have an unmatched provider experience.

• Flexible and 100% remote role (10-20 hrs/week)
• Competitive compensation ($40-85/hour base hourly rate for licensed Master’s-level clinicians, dependent on licensure (level and state), experience, language, etc.)
  
  • Up to 5% of your earnings each quarter as a Mission Bonus (based on the % of students you see who have Medicaid, are uninsured, or speak a non-English language)
• Team-based care model with mission-driven colleagues
• Administrative support from our experienced, full-time Care Coordinators so you can focus on delivering care
• Opportunities beyond clinical care, including working closely with schools on staff support, workshops, and other programming

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student’s life

ABOUT THE ROLE

We’re looking for team-oriented and mission-driven therapists who believe in the power of collaborative care to join our amazing and interdisciplinary care team of psychiatrists, nurse practitioners, therapists, and school health professionals. As a Mental Health Therapist, you'll work directly with school staff, students, and families in our partner school districts to build stronger systems of mental health support.

Role type: 1099 independent contractor (10-20 hours per week)

Location: 100% remote in the United States

Specific Needs: Spanish-speaking therapists

Start date: September 2025

WHAT YOU’LL DO

• 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

WHO YOU ARE 

Must have…

• Passion for working in close partnership with schools on mental health
• Master’s Degree or higher from an accredited school of Social Work, Psychology, Counseling or Marriage, or Family and Child Counseling.
• Active license in Georgia to deliver mental health care independently without supervision (LCSW, LPC, LMFT, or PhD/PsyD, etc.)
• Experience with CBT, DBT, ACT, solution-focused therapy, and/or motivational interviewing
• Experience delivering care via telehealth
• Strong technological skills and learning new systems, including Zoom, GSuite (Google Calendar, Gmail, etc.), electronic health record systems, and other collaboration tools
• Access to a reliable, high-speed internet connection (50 Mbps download, 10 Mbps upload)
  • You can test your internet speed at https://www.speedtest.net/ 
• Excellent organization, communication, and collaboration skills
• Ability to deliver care during our peak hours (Mon-Fri 3-8 pm ET and Sat 8-5) 
• NOTE: As long as you have an active license in the above state, you can live and deliver care from anywhere in the United States

Extra credit…

• Fluency in other languages (e.g., Spanish, Portuguese)
• Experience working in a shorter-term model of care delivery (e.g., 2 weeks to 6 months)
• Experience with parent guidance
• Active NPI number (Need to apply for your NPI? Visit this link: https://nppes.cms.hhs.gov/#/. It takes about 2 to 4-weeks)
• CAQH credentialing set up (Need to apply for CAQH? Visit this link: https://www.caqh.org/providers. It takes about 3 to 4-days)
• Excitement to join an early stage start-up and help bring Cartwheel to more students and school districts

The above is a summary of the role, not an exhaustive list. If you think that you have most of the above but not everything, please apply. We'd love to hear from you.

WHY YOU’LL LOVE CARTWHEEL

At Cartwheel, you’ll have an unmatched provider experience.

• Flexible and up to 100% remote role (10-20 hrs/week)
• Competitive compensation ($55-70/hour base hourly rate for independently licensed Master’s-level clinicians, dependent on licensure, experience, language, etc.)
• Team-based care model with mission-driven colleagues
• Administrative support from our experienced, full-time Care Coordinators so you can focus on delivering care
• Opportunities beyond clinical care, including working closely with schools on staff support, workshops, and other programming

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.