Head of Customer Success

The Role

TrueMark is looking for a founding Head of Customer Success to own the post-sale relationship with our growing base of K–12 district customers. You will be the primary driver of customer health, adoption, retention, and expansion, and you will build the CS function from the ground up.

This is a high-ownership role at a pivotal moment. You'll work directly with the CRO and founders, shape how TrueMark serves schools, and set the standard for what exceptional customer success looks like in responsible AI adoption.

About TrueMark

TrueMark is the leading platform for responsible AI writing instruction in K–12. We help districts uphold academic integrity while teaching students to think critically with AI. Our secure, auditable writing environment combines transparent authorship analytics with a teacher-directed AI assistant so AI becomes a scaffold for learning, not a shortcut.

TrueMark partners directly with districts to define AI policy, train educators, and measure outcomes. We’re building the model for how schools adopt AI with structure, confidence, and integrity.

What You'll Do

Customer Onboarding & Adoption

• Design and execute structured onboarding programs for new district and school customers, from contract close through full deployment
• Serve as the primary point of contact for district administrators, curriculum leads, and teachers throughout the customer lifecycle
• Develop and maintain onboarding playbooks, training materials, and implementation guides tailored to K–12 environments
• Coordinate kickoff calls, educator training sessions, and milestone check-ins to drive adoption and early wins

Retention & Renewals

• Own the renewal process for your book of business, with a strong focus on early risk identification and proactive intervention
• Track and report on customer health metrics, usage trends, and adoption signals to surface churn risks before they escalate
• Conduct regular business reviews with district stakeholders to demonstrate ROI and reinforce TrueMark's value
• Maintain accurate CRM records for all customer activity, milestones, and health scores

Expansion & Growth

• Identify and qualify upsell and cross-sell opportunities within existing accounts, including additional schools, grade levels, or expanded use cases
• Partner with the CRO and sales team to develop expansion strategies and hand off qualified opportunities seamlessly
• Gather customer feedback systematically and translate it into product, marketing, and sales insights

What We're Looking For

• 3+ years of experience in a customer success role, ideally at an early-stage EdTech company serving K–12 districts
• Demonstrated track record of owning renewals, driving adoption, and expanding accounts in a district or school context
• Familiarity with K–12 procurement cycles, district structures, and the rhythms of the academic year
• Experience building or formalizing CS processes, playbooks, or programs in a startup environment
• Strong communication skills and executive presence — comfortable presenting to district administrators and curriculum leaders
• Data-driven approach to customer health: you track what matters and use it to prioritize your time
• Experience with CRM and CS tooling
• Self-directed and resourceful — you can operate with limited structure and build clarity from ambiguity
• Genuine alignment with TrueMark's mission around responsible AI in education

Nice to Have

• Prior experience as a founding or sole CS hire at a seed- or Series A-stage company
• Background in K–12 instruction, curriculum, or school administration
• Experience with writing instruction, academic integrity, or AI literacy programs
• Familiarity with pilot-to-district expansion motions in EdTech

Why Join TrueMark

• Build the CS function from zero — your playbooks, your standards, your team
• Work directly with founders and the CRO on a mission that matters in classrooms across the country
• Join at a moment when responsible AI in schools is moving from conversation to policy — and TrueMark is leading that shift
• Competitive compensation, equity, and benefits in a remote-first, high-ownership environment
• Real career trajectory: this role is designed to grow into VP of Customer Success as the company scales