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Customer Success Associate - ex-educator

Job in Sheffield, South Yorkshire, S5, England, UK
Listing for: Connecting Education
Full Time position
Listed on 2026-09-12
Job specializations:
  • Education / Teaching
Job Description & How to Apply Below

Are you a former teacher or school operations leader, aware of the challenges in schools, and driven to make change? Want to own the customer journey for schools, from the moment they sign, through onboarding, and across every year they’re with us? This might be the role for you!

The company

Our client has built a school management software that schools actually enjoy using. They work with schools across the UK, publish new features every single week, and build in partnership with the schools they serve. They’re anti-modular – delivering one unified experience from attendance to trips, parents’ evenings, payments and exams, with a genuinely modern interface for teachers, parents and students.

They’re also an AI-first company. AI is built into their product and into how they work every day – drafting, analysis, content creation, automation. They move at pace, partly because they let AI do the heavy lifting wherever it sensibly can, and they expect everyone who joins them to work the same way.

They’re scaling towards 1,000 schools. The team is close-knit, ambitious, and based in a modern office in Vauxhall.

The role

They’re looking for a Customer Success Associate who will own the happiness of their schools – from the moment they sign, through onboarding, and across every year they’re with us.

This is not an account management role where you check in once a term and file a report. It’s a role for someone who treats every school as if it were their own, who notices problems before the school does, and who takes genuine pride in a Head of Department saying, “this just works for us.”

Here’s the important part: they won’t get to 1,000 schools by doing everything by hand. A big part of this role, arguably the biggest, is building customer success that scales: onboarding driven by brilliant self-serve guides, videos and in-app resources rather than a calendar full of meetings; training that works at 2am as well as 2pm; and processes designed so the hundredth school onboards with less effort than the tenth.

We think the ideal person has come from a teaching or school operations background. You know how schools actually run – the rhythm of the academic year, why September is chaos, what a Deputy Head cares about – and that empathy is hard to teach. It’s the foundation of this job.

Day to day includes:
  • Build onboarding that scales – own the journey from signed contract to confident daily use, and create the guides, walkthrough videos, checklists and in-app resources that let schools onboard themselves brilliantly
  • Automate relentlessly – turn every recurring manual task into a template, guide or automation, and drive down the effort it takes to bring a school live
  • Keep schools happy and retained – build genuine relationships with the people who use the platform every day; retention is the single most important number in this role
  • Spot problems before they become problems – monitor usage and engagement data, identify schools that are drifting, and act proactively before it ever becomes a renewal conversation
  • Deliver expert training, live and asynchronous – run genuinely useful sessions and turn the best of them into reusable resources that train the next fifty schools without a meeting invite
  • Be the school’s champion when things go wrong – own the relationship even when the fix sits with support or engineering, keeping the school informed every step of the way
The package
  • 6 monthly pay reviews
  • Uncapped training and development budget
  • Fast-growing company with real room for progression and the chance to shape your role
  • Modern office in Vauxhall
  • Weekly team lunches
  • Vibrant team with regular socials – drinks, board games, table tennis and team retreats
  • Opportunity to work in a uniquely high-performance team – if you're…
Position Requirements
10+ Years work experience
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