Director of Customer Success

About Braintrust Tutors

Braintrust Tutors partners with schools and districts to deliver high-impact K–8 academic intervention through exceptional instructional talent, strong operational execution, and a purpose-built platform that supports implementation, visibility, and student progress.

We work in complex, high-stakes school environments where instructional time, staffing capacity, and student outcomes are constantly under pressure. Our programs are strongest when implementation is consistent, communication is proactive, and school partners feel deeply supported. Customer Success is therefore not a secondary function on the sidelines. It is central to retention, expansion, implementation quality, and long-term partner trust.

Why This Role Matters

The Director of Customer Success plays a critical role in ensuring that each school and district receives the full value of the Braintrust program, from onboarding and launch through ongoing delivery, progress monitoring, renewal, and expansion.

This person serves as the connective tissue between district and school stakeholders and Braintrust's internal teams, helping ensure that operational issues are solved quickly, communication is proactive, AI-enabled systems reduce internal burden, and program outcomes remain aligned with the academic goals schools are accountable for delivering.

This is a high-impact, player-coach role for someone who can both manage important relationships directly and build the systems, playbooks, and operating discipline needed to scale the function over time.

The Director of Customer Success reports to the VP of Operations

Position Overview

We are seeking a Director of Customer Success to lead and strengthen the customer lifecycle across our portfolio of school and district partners. In year one, this role will combine direct account ownership with function-building responsibility.

You will initially manage a defined portfolio of partnerships while also building the structure, visibility, and accountability needed for Customer Success to scale. Over time, the role is expected to evolve toward greater team leadership, coaching, and ownership of the broader CS strategy.

The right candidate is strategic, highly organized, operationally sharp, and comfortable working cross-functionally in an environment where service delivery and customer retention are tightly linked.

This is a remote full-time position within the United States.

What You'll Do

Own and grow district relationships.

• Manage a portfolio of school and district accounts across onboarding, implementation, ongoing engagement, renewal, and expansion.
• Serve as a trusted point of contact for partner stakeholders.
• Ensure strong communication, clear follow-through, and a high-quality partner experience.
• Conduct regular account reviews and maintain visibility into partner needs, risks, and opportunities.

Drive retention and renewals

• Build proactive renewal visibility across managed accounts.
• Identify risks early and implement action plans to protect retention.
• Partner with leadership on renewal strategy for strategic or at-risk accounts.
• Support the creation of a more predictable renewal pipeline across the business.

Identify expansion opportunities

• Surface opportunities for growth within existing accounts, including additional schools, student populations, service lines, or program expansion
• Partner with Sales and leadership to help convert expansion opportunities into revenue.
• Ensure Customer Success contributes meaningfully to net revenue retention, not just satisfaction.

Improve implementation quality and customer health

• Monitor key indicators tied to customer success, including onboarding timelines, tutor fill rate, attendance, communication cadence, reporting quality, and program execution.
• Help ensure each account is launched well, supported consistently, and kept on track throughout delivery.
• Build early warning systems for at-risk accounts and operational breakdowns.

Build the Customer Success function

• Develop scalable CS playbooks, workflows, reporting frameworks, and account management rhythms.
  Clarify ownership and handoffs across Customer Success, Operations, Recruiting, Sales, and Product.
• Help define account health, renewal readiness, escalation triggers, and CSM performance expectations.
• Create systems that bring more consistency, visibility, and discipline to the customer lifecycle.

Lead cross-functional execution

• Work closely with Operations, Recruiting, Product, and Sales to ensure customer commitments align with delivery reality.
• Escalate issues early and drive resolution across teams.
• Translate customer feedback and recurring friction points into internal process and product improvements.

Support future team leadership

• As the function grows, support the hiring, coaching, and development of Customer Success Managers.
• Help shape the long-term structure and strategy of the CS organization.

What Success Looks Like

Success in this role is measured by business outcomes, not just activity. This includes:

• Strong renewal visibility and improved retention across the portfolio.
• Earlier identification and mitigation of account risk.
• Clearer account health management and escalation discipline.
• Stronger onboarding and implementation consistency.
• Expansion opportunities identified and advanced within existing accounts.
• Better alignment across Customer Success, Operations, Recruiting, Sales, and Product.
• Increased leadership visibility into customer health, renewal risk, and growth opportunities.

Qualifications

• 5+ years of experience in Customer Success, Account Management, Implementation, Operations, or a related customer-facing leadership role.
• Experience managing complex accounts and driving retention and expansion.
• Experience building or improving systems, playbooks, and processes in a growing organization.
• Strong cross-functional leadership skills with the ability to drive accountability across teams.
• Excellent communication and relationship management skills.
• Comfort operating in a player-coach capacity, balancing strategic ownership with day-to-day execution.
• Strong analytical and organizational skills; able to work with imperfect data and still create clarity.
• High level of ownership, follow-through, and sound judgment.

Preferred Qualifications

• Experience in K–12 education, edtech, tutoring, intervention programs, or district-facing services.
• Experience in a services-enabled business where delivery quality directly impacts retention.
• Experience with CRM and workflow tools such as HubSpot, Notion, spreadsheets, and customer reporting systems.
• Comfort using AI tools to improve efficiency, communication, and internal visibility.

Tools & Systems

Experience with the following is strongly preferred:

• HubSpot.
• Notion.
• Google Workspace.
• Customer reporting dashboards.
• AI productivity tools.
• Braintrust's internal platform and operational systems.

Compensation & Benefits

• The salary range is $100K-$120K annually, with flexibility based on experience.
• Opportunity to earn additional variable commission tied to outcomes such as retention, renewals, expansion within existing accounts, and implementation quality.
• Benefits include medical, dental, and vision coverage.
• 401(k)
• Paid time off and company holidays.
• Professional growth opportunities within a fast-growing company focused on improving outcomes for students nationwide.

Work Environment

Braintrust Tutors is a collaborative, high-accountability environment. The right person for this role is energized by building structure, solving problems, and helping schools succeed in complex operating conditions. You should be comfortable moving between strategic planning, customer-facing relationship management, and internal execution.

To Apply

Please submit your resume and a short cover letter explaining your experience managing customer relationships, driving retention, and building scalable processes in a high-growth or operationally complex environment.

Braintrust Tutors is an equal employment opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other characteristic protected by law. We are committed to creating an inclusive environment that welcomes and celebrates diversity.