What You Will Do
Reporting directly to the Chief Experience Officer and working in close collaboration with the founders and wider ELT. You’ll lead a combined function spanning customer support and customer success, with three direct reports at maturity (Relationship Management Lead, Customer Support Team Lead, Quality & Enablement Manager) and a group-wide team beneath them.
Retention and commercial ownership
* Own the re-enrolment number. This function owns group-wide retention as a primary commercial KPI. When the number moves, you move first. You hold the outcome, and you pull the cross-functional levers to protect and grow it.
* Build the early warning system. Design a family health scoring model that predicts churn before it happens, and stand up the proactive outreach cadences that intervene in time to make a difference.
* Recover and grow. Build structured win-back programs for families who have lapsed, and unlock expansion across Contour Education, MedPrep, and TestPrep through the relationship management layer.
* Raise the service floor. Set, measure, and embed group service standards for response time, first-contact resolution, and complaint recovery. Build the QA and enablement infrastructure to hold the line.
* Lift the experience ceiling. Design the moments that matter across the family lifecycle, from first enrolment through re-enrolment and advocacy. Turn complaints into loyalty moments and routine interactions into reasons to stay.
* Close the gap between pockets of brilliance and group-wide consistency. What works at one campus should work at every campus. What works for Contour Education should shape how MedPrep and TestPrep serve their families too.
Function build and team leadership
* Architect the function. Design the operating model Contour needs at national scale, not a copy of what exists today. Build the business case, defend the investment, and deliver against it.
* Stand up the Relationship Management layer from scratch. This is a net-new capability for Contour. You’ll design the segmentation, cadences, playbooks, and team shape, and hire the leader and the Family Relationship Managers who bring it to life.
* Uplift the Customer Support operation. Take the reactive service centre from where it is today to a metrics-driven, quality-led operation with clear SLAs, scripting, QA, and enablement.
* Build leaders, not just teams. You’ll hire and develop senior direct reports who can carry the function as it scales across states and entities.
Cross-functional partnership
* Partner with Academics. on service quality inputs to retention. You own the outcome. They own the classroom. You make the two work together.
* Partner with Sales and Marketing. on handover, expectation setting, onboarding, referrals, and advocacy. The family lifecycle doesn’t start at enrolment and it doesn’t end at re-enrolment.
* Feed structured insight into the ELT. on what is driving retention, what is eroding it, and what the organisation needs to do about it.
What You Will Bring
You’ve led a customer success, customer experience, or combined service and retention function in a high-growth scale-up environment, and you know what it takes (and feels like). More specifically:
* You’ve owned the retention number. Not influenced it, owned it. You’ve carried re-enrolment, renewal, or churn as a primary KPI for at least three years and you can point to what you did to move it.
* You’ve built the function, not just run it. You’ve designed or materially scaled a customer success or relationship management capability from the ground up, and you can describe the operating model you built and why.
* You’ve run both halves. You understand the mechanics of a reactive service operation (SLAs, QA, workforce planning, ticketing, complaint recovery) and the discipline of a proactive customer success layer (segmentation, health scoring, cadences, playbooks). Strong in one, fluent in both.
* You can write. You understand that experience at scale is a communications problem as much as a service design problem, and you’ve owned the family-facing comms that make or break a moment of truth.
* You’ve earned founder and executive trust. You know how to hold an uncomfortable number in front of an ELT, tell the truth about what’s driving it, and bring a plan to fix it. You manage up, across, and down without losing your edge.
* You can operate in a part-time-heavy workforce. Contour runs on ~400 people, roughly 80% of whom are front-line team. The service operating rhythms, playbooks, and training infrastructure have to work for a team that isn’t in the office five days a week.
* You’re direct. Factual, clear, comfortable being blunt. You push back on peers without drama and hold your team to a standard they thank you for later.
Bonus: Experience in education, professional services, healthcare, or another services business with a recurring customer lifecycle. Experience operating across multiple entities, states, or geographies. Experience using AI and automation to uplift a service or success function.
Why You Will Love It
Most customer success and experience leadership roles sit inside mature SaaS businesses where the playbook is already written, or inside early-stage startups where the scale and runway aren’t there yet. This is the sweet spot: a bootstrapped, profitable, founder-led company at the inflection point between regional success and national brand, and your mandate is to architect the retention and experience engine that carries it there.
* Build the engine. What you build will define how 10,000+ families experience Contour for the next several years.
* Own the commercial outcome. Retention is a real number, owned by a real person, with real levers. That person is you.
* Seat at the table. Direct access to the CXO, the founders, and every senior leader. No bureaucracy between you and the decisions that matter.
* Room to grow. Where this role goes depends on what you build and where your strengths take you.
* Competitive package. $220,000 – $260,000 + bonus + super, flexible hybrid working, EAP, birthday and loyalty leave.
* A mission worth your time. Every family relationship you strengthen flows downstream to students getting into the courses and careers they dreamed about.
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