Cartwheel

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.

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

Therapist

• 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

Engineering Manager

Director, Strategic Finance

Mental Health Therapist, Part-time