Entry-Level Customer Success Implementation Specialist

Squarepeg; Sydney; On-site; AUD 180,000 - 220,000; Full time

Benefits offered by this job

Parental leave

Wellbeing days

Birthday leave

Perks/discounts

Job summary

Squarepeg in Sydney is seeking a Head of Customer Success to build the function from the ground up. You will own the end-to-end post-sale journey, rebuild and lead the onboarding/support team, and drive retention and expansion for a growing allied health SaaS.

You will partner with Product, Marketing and Growth, while developing a data-driven approach to time-to-value and churn reduction as the team scales.

Qualifications

• Built a Customer Success function from scratch at a SaaS scale‑up.
• Data-driven with strong retention and time‑to‑value metrics.
• Experience partnering with Product, Sales, and Growth leaders.

Responsibilities

• Rebuild and lead the onboarding/support team.
• Digitise onboarding with a self-serve portal.
• Own retention, cross-sell and upsell for growth products.
• Partner with Product to influence roadmap and onboarding.
• Collaborate with Marketing on lifecycle campaigns.
• Build data and usage metrics foundation.
• Grow the CS team as the function proves itself.

Skills

Data-driven

Numerate

AI adoption mindset

Hands-on builder

Cross-functional leadership

Job description

Head of Customer Success – Allied Health SaaS Scale-Up

Sydney · 3 days in-office · Reports to the CFO (who runs Sales & Customer Success)

About the Company

Our client is a fast-growing Australian SaaS company building practice management software for allied health providers, used by thousands of practices and tens of thousands of users nationally. They raised a landmark, oversized Series A round off the strength of the product alone — with almost no formal go-to-market motion behind it until now. The business is scaling quickly, expanding into new revenue lines (in‑platform payments and an AI clinical documentation product), and opening a UK market alongside its Australian base.

This is a build-from-zero opportunity: there is currently no dedicated Customer Success function. The existing post‑sale team has never owned retention, expansion, or account management — that gap is entirely this role's to build.

The Role

You’ll own the end‑to‑end post‑sale customer journey for the first time in the company's history:

• Rebuild and lead the existing 8‑person onboarding/support team (plus a growing offshore team), reducing time‑to‑value from today's 2 weeks–3 months
• Digitise the onboarding experience — a customer‑facing self‑serve portal is underway to replace a largely manual, ticket‑based process
• Own retention, cross‑sell and upsell across the company's growth products, for a customer base that's majority month‑to‑month
• Partner closely with Product to influence roadmap and self‑serve onboarding, especially for the high‑churn small‑customer segment
• Partner with Marketing/Growth on lifecycle and adoption campaigns
• Build the data and usage‑metric foundation the business has never had, to understand what drives stickiness and reduce early churn
• Grow the team as the function proves itself — this isn’t a "manage what exists" role, it’s a build

What You’ll Be Measured On

• Reducing early‑stage churn in the self‑serve segment (currently running high single‑to‑low double‑digit % monthly in the first 3 months)
• Lifting overall logo retention, which is currently pulled down significantly by the self‑serve segment relative to larger accounts
• Sustaining/improving strong Net Revenue Retention and Gross Revenue Retention
• Adoption and retention of the company's expansion products post‑sale
• Standing up the team, process and reporting infrastructure this function currently lacks

Compensation

• $180K–$220K base (flexibility to $250K OTE for the right candidate), plus a commission component tied to retention and time‑to‑value metrics
• 12 weeks parental leave, wellbeing leave days, birthday leave, plus other perks/discounts
• No private health insurance

What We're Looking For

• Has genuinely built a Customer Success function from the ground up — ideally at a Series A‑stage SaaS scale‑up — not just managed an existing one
• Highly numerate and data‑driven; comfortable owning retention and time‑to‑value metrics directly
• Strong point of view on AI adoption and using it to drive product stickiness
• A hands‑on builder, not a delegator — the current team isn’t yet at a level to hand things off to
• High energy, "always wired to execute" — this is a fast‑moving, high‑ownership environment
• Comfortable operating at peer level with Product, Sales, and Growth leadership

Interview Process

• Initial 20–30 min culture‑fit conversation
• Technical round / case study on CS strategy, metrics and retention approach
• Final rounds with HR and the CEO (a board conversation may be added for finalists)