Fast Facts

We are seeking a mission-driven Vice President of Customer Success to lead our team at Tutored by Teachers, enhancing long-term partnerships within school districts and ensuring our tutoring programs deliver maximum value to support student outcomes.

Responsibilities: Key responsibilities include team leadership and development, managing retention and growth strategies, designing customer journeys, and driving innovation through cross-functional initiatives.

Skills: Required skills include experience in customer success and operations, excellent relationship management, strong communication abilities, and a strategic mindset with a passion for education equity.

Qualifications: Preferred qualifications are 10+ years of experience in relevant fields, successful team management, designing customer success strategies, and adaptability in a fast-paced environment.

Location: The position is fully remote, allowing flexibility in work location without specified travel requirements.

Compensation: Not provided by employer. Typical compensation ranges for this position are between $150,000 - $230,000.

At Tutored by Teachers (TbT), we have scaled our mission to advance equity in education by serving tens of thousands of students with personalized learning. Partnering with a diverse array of school districts across the country, we now seek a talented and mission-driven leader to join our team. As Vice President of Customer Success, you’ll ensure that our school and district partners get maximum value from our high-dosage tutoring programs—supporting student outcomes and strengthening long-term partnerships across the country.

The Role:

We’re looking for a strategic, service-driven leader to join as our Vice President of Customer Success. This role is all about building deep, lasting relationships with our district and school partners—and building the systems, playbooks, and team needed to scale that experience across the country.

You’ll lead a team of Engagement Managers (EMs) responsible for implementation, ongoing support, and expansion within our partner accounts. You’ll ensure the team is set up to meet retention and growth targets, and you’ll play a critical role in defining how we deliver value—efficiently, consistently, and with the high level of service that is a key differentiator of how we do business.

We recently completed a refresh of our customer segmentation strategy, designed to help us spend more time with our highest-potential customers and deliver excellent service at the right level for all. In this role, you’ll bring that strategy to life.

In this role, your core responsibilities will include:

Team Leadership & Development

• Establish and manage toward the long-term vision for the Customer Success organization in alignment with TbT’s growth strategy and mission
• Lead and scale a high-performing Engagement Management team, building the structure, systems, and culture needed to deliver exceptional experiences and outcomes at scale
• Own team capacity planning and headcount strategy to ensure resources align with customer segmentation and business priorities
• Champion a culture of accountability, learning, and service excellence across the post-sale organization

Retention & Growth Strategy

• Own retention and expansion targets across our portfolio of accounts
• Equip the team with playbooks, tools, and customer insights to enable strategic renewals and growth
• Establish and maintain a real-time view of customer health across the portfolio—defining signals and leading indicators that require intervention or may foreshadow churn
• Partner closely with Sales and Account Executives to grow accounts from multiple angles and foster a culture of collaboration
• Be data informed and work the BizOps team to forecast renewals and track growth

Customer Experience & Operational Execution

• Design and operationalize customer journeys that meet the needs of diverse customers while remaining scalable
• Be a strategic thought partner and occasional executive sponsor on high-stakes accounts
• Champion the voice of the customer internally - working across teams to improve our offering, delivery, and service models

Innovation & Strategic Initiatives

• Maintain an evolving perspective on the role of AI and automation in service delivery, identifying opportunities to improve efficiency without sacrificing quality and trust
• Lead cross-functional initiatives to improve our overall customer experience and internal systems
• Track success metrics and share insights regularly with senior leadership

Requirements

There’s no such thing as a perfect candidate—if you feel excited by this role and believe you can thrive in it, we encourage you to apply even if you don’t check every single box.

Traits that we've found lead to success in this role include:

• 10+ years of experience in customer success, account management, operations, or a related field, ideally in a service-based or tech-enabled services organization
• A track record of managing and scaling teams, including coaching managers and building strong team culture
• Strong enterprise relationship management experience—especially with complex, multi-stakeholder clients (education, healthcare, public sector, or similar)
• Experience designing and implementing customer success strategies, including segmentation, playbooks, and account planning
• Excellent communication and influencing skills, with the ability to inspire a team and build trust with executive-level partners
• An operator’s mindset: strong process builder, project manager, and strategic thinker who can also roll up their sleeves
• Comfort working in a fast-paced, evolving environment—TbT is a startup, and that means adaptability is key
• A passion for education equity and a belief in the power of high-dosage tutoring to change student outcomes

What can you expect in your first year?

Within 1 month

• Build deep context on TbT’s programs, current clients, and internal operations
• Shadow EMs and Sales team members to understand the full customer lifecycle
• Begin identifying opportunities for team and process improvement

Within 3 months

• Take full management responsibility for the EM team
• Launch initial updates to team operations, client communications, and account planning
• Align with Sales and Finance on customer forecasting and growth goals

Within 6 months

• Drive measurable improvements in customer retention and account health
• Implement systems and playbooks that increase EM capacity and customer satisfaction
• Serve as executive sponsor or escalation point on key accounts

And beyond

• Build a scalable, high-performing Customer Success organization
• Drive customer experience strategy across the company
• Play a central role in TbT’s long-term growth and impact on students across the country

Traits We Want to See in Everyone:

Adapted from Carrol Chang, CEO of Andela

• Low ego, low drama, servant leader. You share credit, take blame. You like being wrong because it means someone else had an even better idea. 
• One team mentality. You break silos across teams. You put the company and mission first above your team alone.
• Great listener, hungry for feedback. You’re always seeking to improve – our product, our business, yourself. You solicit diverse opinions and deeply listen.
• Owner, not renter. You see a problem, you fix it or find someone who will. The buck stops with you.
• Player-coach. You fly high (create strategy) AND low (know the details that matter). You roll up your sleeves and get scrappy. You do this without micromanaging, empowering your team while actively engaging in important details.
• Business problem solver. You’re not just a functional expert; you consistently get praise for approaching your function through the lens of solving business problems.
• Information worker. You aggressively, directly, and succinctly communicate up, down, left, and right using the right channels.
• 100% healthcare coverage for you and your family
• Access to 401k to help save for the future
• Well-rounded wellness benefits, including access to free and low cost mental health resources and support services
• Fully remote work environment and a flexible schedule
• Annual in-person team retreats
• 3 weeks of vacation in the first year and an unlimited vacation policy after year 1 to help recharge
• The chance to make a meaningful impact on students' lives and contribute to the advancement of educational equity.