Head of Payments

About the Company

Compass is working to reshape the school experience for educators, students, parents, and administrators through technology that simplifies day-to-day operations and helps schools focus on learning and growth. The business has expanded into a global scale-up serving more than 5,000 schools across three countries, supported by a team of over 300 people. Payments is a major growth priority, and the company is seeking a leader to take full ownership of this area.

Role Overview

As Head of Payments, you will report to the Chief Revenue Officer and lead the end-to-end go-to-market strategy for the payments product. The role is centered on expanding adoption within the existing school base while also ensuring payments is positioned in every relevant new-school conversation. You will manage a team of two payments specialists and work closely with the broader sales organization to drive revenue, increase attach rate, and grow active usage across the customer base.

Key Responsibilities

• Own the full payments GTM plan, including targets, segmentation, territory planning, and quarterly priorities.
• Set and deliver on revenue, attach rate, and adoption goals across both the current customer base and new opportunities.
• Create the sales playbook for payments, covering discovery, value messaging, objection handling, commercial structure, and competitive differentiation.
• Expand usage within the existing school base by moving schools from awareness to activation and then to full adoption.
• Build and run adoption programs that increase parent transactions, live use cases, and transaction volume through Compass payments.
• Identify the segments, geographies, and customer profiles most likely to adopt payments successfully.
• Work with the core sales team to make sure payments is included, scoped, and sold wherever it fits in new-school deals.
• Support account executives with the tools, training, and deal support needed to close payments alongside the main platform.
• Lead, recruit, and develop a high-performing team of payments sales representatives and adoption specialists.
• Establish the operating rhythm for pipeline reviews, forecasting, deal inspection, and adoption reporting.
• Coach the team on consultative selling, business case development, and navigating school decision-makers.
• Partner with the CRO and revenue team on strategy and forecasting, collaborate with Marketing on payments-focused campaigns, and share customer feedback with Product to remove adoption blockers.

What We’re Looking For

This role suits a commercially strong sales leader who is comfortable operating in a scale-up environment, enjoys building new motions from the ground up, and can drive both adoption and new revenue.

• At least 7 years of experience in B2B SaaS or payments sales, including 3 or more years leading a sales and/or adoption team with revenue responsibility.
• A proven record of increasing product attach and adoption within an existing customer base, not only closing net-new business.
• Strong commercial judgment, including comfort with pricing, deal structuring, and customer business-case development.
• Experience selling payments, fintech, or other financial products, especially where customers needed to switch providers or activate new payment flows.
• Ability to build a GTM motion from scratch, including segmentation, messaging, enablement, and measurement.
• Confident forecasting discipline and comfort working in a metrics-led revenue organization.

Preferred Background

• Experience selling into schools, education, or other community- or membership-based sectors.
• Exposure to Australian payments products such as cards, direct debit, BPAY, and PayTo, along with their commercial considerations.
• Experience working with a wider sales organization to launch embedded or attached products.

Benefits

• Hybrid working across office hubs.
• Learning and development support, including a dedicated professional development budget.
• 24/7 Employee Assistance Program access, with face-to-face, phone, and live chat support.
• Parental leave support for both primary and secondary carers.
• Regular team events, social budgets, and in-office perks such as team lunches and end-of-week socials.
• Employee referral program.
• A supportive and inclusive workplace where employee input is encouraged and valued.

Additional Requirements Before Employment

• Satisfactory National Police Check.
• Valid Working With Children Check.
• Proof of unrestricted work rights in Australia, such as citizenship, passport, or birth certificate.

Equal Opportunity

Compass is an equal opportunity employer and values diversity, inclusion, and a workplace where everyone feels welcome.

Application Note

If you are motivated by the chance to build, own, and scale payments go-to-market strategy within a growing SaaS business, this could be a strong fit.