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Engineering Manager

Remote

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.

ABOUT THE ROLE

As an Engineering Manager at Cartwheel you have the unique opportunity to design and implement a modern approach to how hardware and software are managed in a hypergrowth company. This role is particularly exciting, because it serves industries that historically haven’t prioritized user experience – healthcare and education. In this role, you will report directly to the CTO and lead your team to support the strategic planning and software development processes of a 25-person R&D organization. At Cartwheel, we fundamentally believe that technology is a critical part of delivering optimal mental healthcare to the student population we serve. 

Role type: This is a W2, Full-Time, Salaried position

Location: Remote, based in the United States

Start date: October 2025

WHAT YOU'LL DO

Strategic Engineering Leadership

  • 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.

Operational Excellence

  • 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.

Team Development & Culture

  • 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.

Cross-Functional Partnership

  • 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.

WHO YOU ARE 

Must have…

  • Passion for our mission to tackle the youth mental health crisis
  • 6+ years of relevant engineering experience
  • Proven track record of planning and delivering successful engineering projects 
  • Deep understanding of engineering best practices
  • Strong affinity toward data-driven thinking by measuring and iterating on processes.
  • An owner-mindset that drives you to improve the company even when it means stepping outside of a traditional engineering role
  • Experience with high growth companies and corresponding engineering related challenges 
  • Strong analytical and problem-solving skills. 
  • Excellent communication and collaboration skills. 
  • Customer-centric focus with ability to translate technical solutions to business value
  • A curiosity driven by first principles thinking in service of reimagining how technology can improve healthcare and education
  • At times, work efficiently under high levels of pressure and demanding timelines.

Extra credit…

  • Experience working as an engineering manager in early stage technology startups
  • Knowledge of Ruby on Rails tech stacks and how to evolve them in growing organizations.
  • Possess a degree in Information Technology, Computer Science or a related field
  • Experience in healthcare and/or Ed. Tech

Skills…

  • Project Management: Excellent project management skills with the ability to coordinate across many stakeholders and prioritize tasks
  • Technically Savvy: Fluency in modern tech stacks with an ability to quickly learn new technologies. 
  • Relationship Builder: Experience with building relationships across diverse stakeholders and influence without authority
  • Strong Communicator: Superb written and verbal communication skills 
  • Organized thinker: Instinctively structures problems into logical components

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 between $180,000 - $220,000
  • Generous PPO medical, vision, and dental coverage
  • Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
  • 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

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 opportunities regardless of race, color, religion, ancestry, national origin, gender, sexual orientation, disability status, or veteran status.

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