Director of Customer Success

Director of Customer Success itopia · Miami, FL preferred (Remote considered for the right candidate) · Full-Time

itopia is hiring a Director of Customer Success to own the post-sale outcome for the largest K-12 school districts in the country. Our customers include Houston ISD, NYC Public Schools, Miami-Dade County, and Cy-Fair ISD. The next 24 months will define whether itopia becomes the platform of record for the top 100 districts nationally — and the answer to that question is decided in customer success more than anywhere else.

This is a builder seat. itopia has a working CS motion, marquee logos, and a clear product wedge. What we don't yet have is a unified post-sale operating model — IT onboarding, teacher enablement, AI and policy adoption, renewal motion, and executive QBRs all running on one playbook, measured against the same outcomes. You will build that. You will also run it personally for our top accounts until the team you hire under you can.

You will own gross retention, net retention, and reference-ability for the entire customer base, and you will be measured on all three. This role reports to the executive team and sits at the same level as the heads of Sales and Product.

About itopia

itopia is a K-12 cloud computing platform that gives districts a single place to deliver and control Windows applications, SaaS tools, AI tools, YouTube, and browser extensions — all under a unified policy and visibility engine. Our buyers are IT and Curriculum directors at large K-12 districts, and we're focused on becoming the platform of record for the top 100 districts nationally.

We serve districts including Houston ISD, NYC Public Schools, Miami-Dade County, and Cy-Fair ISD, and operate 100% through a channel-first model with CDW, Trafera, Howard Technology Solutions, Vivacity Tech, and other leading education resellers.

We're a lean, high-output team. We move fast, we don't overthink, and we build things that actually get used in schools.

Responsibilities

• Own gross retention, net retention, and customer health across the entire book — every named account, every renewal, every expansion conversation runs through this seat
• Build and own itopia's onboarding playbook for new districts — structured 60-day implementation covering identity integration, app packaging, classroom management rollout, policy configuration across SaaS/AI/YouTube/extensions, IT staff enablement, and instructional staff enablement, with a documented plan delivered to the district within 10 business days of contract signing
• Run the District Technology Advisor model — every strategic district gets a named single point of contact for platform strategy, escalation, and relationship management. You own the model, the standards, and the staffing of it
• Build itopia's teacher and IT training program — recurring, refreshed with every platform release, covering policy management, AI tool governance, classroom management features, and new capabilities as they ship. Delivered live, on-demand, and embedded in the product
• Own the renewal motion end to end — forecast, negotiation, multi-year prepay structuring with channel partners, and close. For complex multi-year renewals you partner with Sales and CDW; for standard renewals you and your team own the outcome
• Drive expansion within the installed base — school-by-school growth inside committed districts, new persona adoption (curriculum leaders, instructional technology, classroom teachers), and pull-through of AI governance, browser, and YouTube control adoption
• Run executive QBRs with the largest districts — the CIO/CTO dashboard, ROI reporting, adoption trends by school, AI tool usage, and the strategic roadmap conversation. These need to be earned reviews that the district actually wants on their calendar
• Own customer health scoring and the early warning system — usage trends, adoption velocity, ticket sentiment, and exec engagement rolled into a forecast you defend weekly with the executive team
• Partner with Product on the feedback loop — feature requests, configuration patterns, district-specific needs, and platform gaps surface through you and feed directly into the roadmap
• Partner with Sales on the handoff — own the joint kickoff, the implementation commitments made in the sales cycle, and the relationship continuity from signed contract to first renewal
• Build the team — hire and develop Customer Success Managers, Implementation leads, and Training specialists as the book grows. You'll start hands-on with the largest accounts and scale the function from there
• Maintain support SLA discipline across the function — P1 1-hour response, P2 4-hour response, P3 next business day — and own the relationship with our support operation to make sure those numbers are real
• Represent the customer voice in every executive meeting — what's working, what's breaking, what's coming, and what we need to fix before it becomes a renewal risk

Qualifications

• 7+ years in Customer Success, with 3+ years leading the function — SaaS strongly preferred, EdTech a significant advantage
• Demonstrated ownership of gross retention, net retention, and expansion in a complex enterprise SaaS environment with multi-stakeholder customers
• Experience selling and renewing through channel partners — CDW Education, regional resellers, or comparable VAR/distributor motion
• Experience building a CS function from a working motion into a structured, scalable operation — playbook design, segmentation, health scoring, and team hiring
• Comfortable owning both the IT and instructional sides of the customer — you understand that a successful K-12 deployment is not just an IT project, and you can run a teacher training program with the same rigor you run an executive QBR
• Strong commercial instincts — you can structure a multi-year prepay, negotiate a renewal, and defend a forecast with the same confidence as a sales leader
• Experience with K-12 districts, state and local government, higher education, or other large decentralized institutional customers is a significant plus
• Exceptional executive presence — you'll be the named District Technology Advisor for our largest accounts and the face of itopia post-sale
• Self-directed, hands-on, and comfortable building structure in ambiguity — you will be running the function and doing the work simultaneously for the first 6 to 12 months
• Genuine interest in education — our customers care about kids, and so should you

What Success Looks Like in Year One

By the end of your first 90 days, you will have audited every active customer, built a unified onboarding playbook, defined the District Technology Advisor model, and personally run executive reviews with our top 5 accounts.

By the end of your first 12 months, gross retention is above 95%, net retention is above 115%, every strategic district has a named DTA, the teacher and IT training program is live and refreshed with every release, and you've hired the first two members of your team.

Our Culture

itopia operates a 100% channel-first model and a lean, high-output team. We move fast, we don't overthink, and we build things that actually get used in schools. We believe winning is engineered, not accidental — playbook by playbook, district by district, renewal by renewal. The Director of Customer Success is one of the most important hires we will make this year, because everything we're building in Sales depends on customers staying, growing, and telling other districts about it.

If you are driven by a big market that hasn't been fully taken, a product you can genuinely believe in, and a culture where your contribution is visible and valued — this is the right place to build your career.