Director of Customer Success

Prologue is proud to partner with a leading K–12 learning platform revolutionizing how educators and students engage with AI-powered tools in the classroom. Backed by fresh Series A funding, our client is growing rapidly and looking to hire their first-ever Director of Customer Success to lead and scale their post-sale experience.

What They’re Looking For:

• 7–10+ years of B2B SaaS Customer Success experience (EdTech preferred)
• Background in managing teams of 6–8+ CSMs, ideally across the K–12 or education space
• Strategic and operational mindset—can build process and playbooks while coaching team execution
• Bonus if you’ve worked in high-growth, venture-backed startups with evolving product cycles

What You’ll Be Doing:

• Own the post-sale customer lifecycle across K–12 districts and schools
• Manage and grow a team of 6–8 Customer Success Managers
• Build systems to scale onboarding, renewals, adoption, and expansion
• Collaborate with Product, Sales, and Implementation to drive value and retention

Compensation & Benefits:

• OTE: $175,000 – $200,000 + Equity
• Health, dental, vision coverage
• Flexible PTO and remote-first environment
• Mission-driven team focused on transforming K–12 outcomes through AI

This is a defining leadership opportunity to shape the Customer Success org from the ground up—ideal for someone who thrives in early-stage environments and has a strong grasp of what it takes to build retention, engagement, and outcomes for school districts.

Interested?

Apply below or reach out directly to urszula@prologuerecruit.org with your updated CV to learn more or express interest!