Join Cartwheel to help tackle the student mental health crisis. 

Kids spend most of their days in the classroom. And teachers and staff, who play a vital role in their development, are often the first to notice when something is off. But with 1 in 5 young people struggling with mental health, schools are getting crushed by a downward spiral in student crises and staff burnout.

With large increases in federal funding for schools and the rise of telehealth, schools are reimagining what mental health support can look like. 

Cartwheel is an early-stage startup building technology-enabled mental health services that put schools at the center. We see our role as supporting on-campus counselors, psychologists, and school social workers who see kids every 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 the Success Enablement Manager, you will be a critical member of our small but growing Success team. You’ll build scalable processes, tools, and content that support the customer lifecycle—from onboarding through renewal—empowering both customers and internal teams to deliver a seamless experience. As a strategic partner to the School Success team, you will work closely with program managers (CSMs), sales, marketing, and product teams to ensure that every customer interaction adds value and aligns with our vision for long-term success.

You’ll have the unique opportunity to shape the future of success at Cartwheel by designing scalable processes, playbooks, and content that will enable our team to grow and our customers to thrive. As an early member of the team, you will be integral in iterating and building out the role as we scale.

Role type: Full-time

Location: Remote with quarterly in-person team retreats and co-locating as needed in Boston, especially as we get to know each other. While you can be located anywhere in the US, this role requires EST or CST working hours.

Start date: Fall/Winter 2024

WHAT YOU’LL DO

• Build and implement scalable systems, tools, and processes to streamline the post-sales customer lifecycle, including onboarding, adoption, retention, and expansion.
• Develop and optimize content creation for onboarding guides, playbooks, training materials, customer resources, and internal documentation to support both internal teams and customers.
• Collaborate with Program Managers (CSMs) and cross-functional teams (sales, product, marketing) to improve customer experiences and drive consistent delivery.
• Partner with the Success team to gather feedback, create streamlined handoff processes from sales to success, and ensure smooth ongoing support.
• Create and implement training programs for internal teams to ensure consistent use of new tools and processes.
• Drive the adoption and effectiveness of Success tools like CRM and customer communication platforms, while managing internal enablement programs to upskill team members.
• Work closely with Success leadership to set and track key performance metrics, analyze data, and use insights to drive process improvements.
• Stay up-to-date on best practices and industry trends to continually improve customer success initiatives.
• Flex into direct customer work as needed to learn and support the growing needs of the team.

WHO YOU ARE 

• Applicable Experience: 3+ years in customer success, enablement, or operations plus 5+ years in education, education technology and/or health technology, preferably in a startup environment.
• Process Builder: You have experience developing scalable customer success processes and implementing systems from scratch, ideally in a startup or high-growth environment.
• Technologically Savvy: You’re comfortable using Google Suite (slides and sheets), CRMs (like Salesforce, HubSpot) and customer success tools, with a proven ability to quickly learn and adapt to new technologies.
• Relationship Builder: You excel at creating strong relationships with internal teams and customers, promoting trust, and fostering collaboration.
• Strategic and Analytical Thinker: You use data and feedback to guide decision-making and optimize processes for efficiency and scalability.
• Communicator: Your written and verbal communication skills are top-notch, and you can clearly articulate processes, strategies, and needs across teams.
• Mission-Driven: You’re passionate about providing customers with a seamless experience and are driven by the challenge of building something impactful from the ground up.
• Adaptable and Entrepreneurial: You thrive in a fast-paced, evolving environment where you can make a significant impact and help shape the company’s direction.

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: 

• Competitive Compensation: Salary range of $90,000 to $105,000
• Team-based culture and a passionate, close-knit team where your work directly impacts the company and the customers we serve
• Excellent health insurance
• Meaningful equity ownership stake
• Flexible paid time off
• 100% remote with quarterly team meetups, and a collaborative culture
• 401K with employer match
• Be a part of a fast-growing company and have the chance to shape the future of our Success Enablement program
• $500 annual educational stipend
• Macbook

If you’re ready to help us build a customer success program from the ground up and thrive in a startup environment, we’d love to hear from you! Even if your experience doesn’t perfectly match the job description, if you bring other relevant skills or a passion for customer success, we encourage you to apply.

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.