Senior Manager / Director of Account Management

Cartwheel•Cambridge, MA

5d•$150,000 - $162,000•Remote

About The Position

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

Requirements

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 Haves

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

Responsibilities

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
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
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
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

Benefits

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