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Join to apply for the Head of Customer Success role at Orah Join to apply for the Head of Customer Success role at Orah Get AI-powered advice on this job and more exclusive features. Operations Manager at Orah (Previously Boardingware) About Orah Orah is the dutyofcare platform that helps K12 schools know where every student is, how theyre doing, and what they need next . Trusted by leading independent schools across Australia, North America and the UK, we give educators realtime insights so every student can thrive. Were a 35person EdTech SaaS company with a growing Toronto hub (three teammates on the ground today). Were ready to welcome a handson Head of Customer Success who will reverse churn, inspire the team, and deepen our human connection with every school. The mission Own the full postsales journey so that every customer: Renews - drive Gross Dollar Retention 95% within 12months. Feels heard - sees product improvements shipped from their feedback. Youll lead: 3 Customer Success Managers 2 Onboarding Specialists 1 Support Representative ...and partner daily with Product, Sales and Engineering. What youll do Jump on calls, video or planes (minimum every 6weeks infrontofcustomer, mostly US) to derisk atrisk accounts and uncover expansion paths. Execute healthscore driven playbooks and quarterly business reviews (QBRs) for every school. 2. Build a culture of human connection Coach the team to default to phone/video/onsitenot emailso relationships stay personal. Model urgency, clarity and accountability; celebrate wins publicly and surface blockers fast. Launch a 30day TimetoValue milestone framework with shared visibility for Sales, CS and Product. Publish CSAT & deployment metrics that predict renewal. 4. Champion the voice of the customer Distil feedback into a ranked backlog each quarter and track features shipped vs churn drivers. Influence the roadmap with databacked proposalslatitude granted when workarounds are exhausted and customer risk is tangible. 5. Strengthen process & tooling Refine (not hide behind) tools like HubSpot and Vitally; guide a RevOps resource to build dashboards, workflows and reporting. Create concise, singlesource playbooks for renewals, QBRs and account management. 6. Lead & develop the team (informally for now) Playercoach: shadow calls, run deal reviews, mentor career paths. Keep structures lightweight until headcount growsfocus on execution over bureaucracy. What makes you a great fit 58 yrs postsales leadership in B2B SaaS (ACV $1030k) with a track record of reducing churn and lifting NRR at companies. Able to resonate with K12 school leadersunderstand the peoplefirst, missiondriven mindset of educators. 70% intheweeds / 30% strategic: youre as happy flying to a boarding school to save an account as you are framing a quarterly CS strategy. Curious operator who can tinker in HubSpot/Vitally enough to brief Ops but doesnt need to be the poweruser. Behavioural DNA: Bias for Action , Followthrough , Strong Convictions Loosely Held . Based in/near Toronto and able to join the team inoffice two days per week; comfortable with US travel every 6weeks. Note: Please apply using the following link : When prompted to upload your CV, please upload it in pdf format only. Seniority level Seniority level Director Employment type Employment type Full-time Industries Education Administration Programs Referrals increase your chances of interviewing at Orah by 2x Sign in to set job alerts for Head of Customer Success roles. Were unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI. #J-18808-Ljbffr