Senior Manager / Director of Account Management

ABOUT THE ROLE 

We're looking for a strategic, operationally excellent Senior Manager / Director of Account Management to lead our renewal and expansion motion. Reporting to the VP of School Success, you will mature and scale our Account Management function, establishing best-in-class practices for a complex, high-touch vertical.

This role is for someone who has carried a number, built post-sale teams from an early stage, and knows how to combine consultative selling methodology with a rigorous operational approach to drive forecast quality and observability. You'll lead a team of Account Managers across SMB, mid-market, and enterprise school district segments.

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

Location: Remote, based in the United States

Start date: March 2025

WHAT YOU’LL DO

Team Leadership & Development

• Build a high-performing Account Management team that consistently meets and exceeds retention and expansion quotas
• Provide hands-on coaching and development to Account Managers
• Establish clear performance standards, success metrics, and career progression frameworks

Retention & Expansion Strategy

• Drive post-sale outcomes including GRR, NRR, and expansion revenue 
• Set playbooks for lifecycle management including mid-year business reviews, renewal conversations, expansion opportunities, and risk mitigation
• Build scalable processes and infrastructure to make the renewal process observable and predictable
• Implement best practices from consultative methodologies tailored to the education vertical

Cross-Functional Collaboration

• Partner closely with Customer Success Managers, Marketing, and Product to align on customer outcomes
• Serve as a sponsor for key accounts and complex renewals
• Work with Revenue Operations, Finance, and leadership on forecasting, capacity planning, and go-to-market strategy

Strategic Leadership

• Define and refine go-to-market strategy for renewals and expansion as we scale
• Identify innovative ways to improve team performance and customer outcomes
• Take an entrepreneurial, hands-on approach—willing to jump into accounts, test new approaches, and solve problems creatively
• Challenge the status quo when logic and data require it; see something broken, fix it

WHO YOU ARE

Must Haves…

• 7-10+ years of experience in Account Management, Customer Success, or renewal-focused sales roles
• 5+ years managing client-facing teams in fast-paced, high-growth environments
• 3+ years of experience managing managers
• Proven track record as a top-performing account manager or renewal executive who has personally carried a number
• Experience scaling post-sale motions and building repeatable plays
• History of consistent team quota attainment via renewals, upsells, and expansion (not just license expansion)
• Deep familiarity with consultative selling methodologies and complex B2B buying environments
• Strong quantitative orientation—comfortable owning dashboards, forecasts, metrics, and executive reporting
• Exceptional communication skills and executive presence; ability to influence senior decision-makers
• Highly organized, self-motivated, detail-oriented with excellent follow-through
• Strong analytical skills and comfort with data-driven decision making
• Ability to build scalable, repeatable processes while maintaining customer-centricity

Nice to have…

• Experience in education technology, healthcare, government/public sector, or other mission-driven verticals
• Understanding of K-12 education systems, school district operations, or student support services
• Familiarity with mental health services, telehealth platforms, or clinical operations
• Experience with customer success platforms (ChurnZero, Gainsight, etc.) and CRM systems

LEVELING NOTE: 

This role may be hired at the Senior Manager or Director level depending on experience and demonstrated scope. Regardless of level, this role owns retention and expansion outcomes and is expected to operate with a high degree of accountability and autonomy.

• Director-level candidates will have experience scaling post-sale revenue motions across segments, managing managers, and owning forecasting and GTM strategy.
• Senior Manager candidates will have deep hands-on leadership experience, strong renewal and expansion ownership, and clear readiness to grow into broader strategic and people leadership over time.

WHAT MAKES THIS ROLE UNIQUE

• Mission-driven work: Every renewal means continued mental health support for students who need it most
• Strategic impact: Shape the retention and expansion strategy during a critical growth phase
• Complex partnerships: Navigate multi-stakeholder environments including superintendents, assistant superintendents, student services directors, and school boards
• Innovation opportunity: Build on existing playbooks and develop new approaches to drive customer value

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 $150K–$162K base + 30% variable (OTE ~$210K)
• 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
• Macbook