About Orah
Orah is the duty‑of‑care platform that helps K‑12 schools know where every student is, how they’re doing, and what they need next. Trusted by leading independent schools across Australia, North America and the UK, we give educators real‑time insights so every student can thrive.
We’re a 35‑person EdTech SaaS company with a growing Toronto hub (three teammates on the ground today). We’re ready to welcome a hands‑on Head of Customer Success who will reverse churn, inspire the team, and deepen our human connection with every school.
The mission
Own the full post‑sales journey so that every customer:
- Renews - drive Gross Dollar Retention ≥ 95 % within 12 months.
- Grows - lift Net Revenue Retention ≥ 115 % by expanding use cases & modules.
- Feels heard - sees product improvements shipped from their feedback.
You’ll lead:
- 3 Customer Success Managers
- 2 Onboarding Specialists
- 1 Support Representative
…and partner daily with Product, Sales and Engineering.
What you’ll do
1. Churn defence & expansion (70 % hands‑on)
- Jump on calls, video or planes (minimum every 6 weeks in‑front‑of‑customer, mostly US) to de‑risk at‑risk accounts and uncover expansion paths.
- Execute health‑score 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/on‑site—not email—so relationships stay personal.
- Model urgency, clarity and accountability; celebrate wins publicly and surface blockers fast.
3. Systemise onboarding
- Launch a 30‑day Time‑to‑Value 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 data‑backed proposals—latitude 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, single‑source playbooks for renewals, QBRs and account management.
6. Lead & develop the team (informally for now)
- Player‑coach: shadow calls, run deal reviews, mentor career paths.
- Keep structures lightweight until headcount grows—focus on execution over bureaucracy.
What makes you a great fit
- 5–8 yrs post‑sales leadership in B2B SaaS (ACV $10–30 k) with a track record of reducing churn and lifting NRR at < $10 m ARR companies.
- Able to resonate with K‑12 school leaders—understand the people‑first, mission‑driven mindset of educators.
- 70 % in‑the‑weeds / 30 % strategic: you’re 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 doesn’t need to be the power‑user.
- Behavioural DNA: Bias for Action, Follow‑through, Strong Convictions Loosely Held.
- Based in/near Toronto and able to join the team in‑office two days per week; comfortable with US travel every 6 weeks.
Please apply using the following link :
https://orahai.app.n8n.cloud/form/2a87705d-8ba1-41f1-80ef-85f364ce253e
When prompted to upload your CV, please upload it in pdf format only.
Job Type: Full-time
Pay: $140,000.00-$170,000.00 per year
Additional pay:
- Commission pay
Benefits:
- Dental care
- Extended health care
- Paid time off
Schedule:
- Monday to Friday
