Back to jobs
New

Senior Manager / Director of Account Management

Cambridge, MA

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

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.

We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization

Note: Please do not contact our Care, Provider, or Patient Services lines regarding job postings or application status. These teams support our patients and families and are not involved in the hiring process. For all recruitment-related questions, please email talent@cartwheelcare.org.

Create a Job Alert

Interested in building your career at Cartwheel? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Select...
Select...
Select...
Select...
Select...
Select...
Select...
Select...
Select...

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Cartwheel’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.