Head of Sales and Customer Success

Meet Wingman Group

• Founded: 2022
• Location: Brisbane, Australia
• Product: Offshoring & Workforce Solutions, Real Estate & Property Services
• Funding: Bootstrapped / Founder-led

The Story

Three and a half years ago, Wingman Group set out to do offshoring differently. Today, they're one of the most recognised names in real estate services, and the growth speaks for itself.

While most offshoring providers stop at placement, Wingman goes further. They fully train their team in real estate operations and embed them directly into client businesses, bringing the right processes and systems along with them. It's an approach that's earned real trust across the industry, with over 800 businesses and 1,200 staff now part of the Wingman network.

Bootstrapped and founder-led, it's a business that moves quickly, thinks ahead, and has built a culture worth being part of.

The Role

Wingman's client base is growing fast, and so is the depth of those relationships. As the business scales, ensuring every client gets the most value from their partnership with Wingman is a top priority, and this role plays a critical role in that.

This is a senior leadership position with ownership of both the customer and sales functions across Australia and New Zealand.

On the customer side, you'll lead a team of six (growing to eight or nine within months) and own three core pillars: onboarding delivery, retention and portfolio management, and organic growth from within the existing client base.

On the sales side, you'll lead a growing Sales and Growth team, currently comprising a Business Development Manager and a Sales Development Representative, with scope to expand as the business grows. Together, these two functions cover the full client journey from first conversation through to long-term partnership.

This is a builder's role. The foundations are in place, and your job is to take it to the next level through real KPI accountability, churn prediction and customer stability analysis, and ensuring teams across both functions are delivering to a consistently high standard.

Day to day, you'll:

• Lead and develop a combined team spanning customer success and sales
• Own onboarding, retention, and expansion across 800+ client businesses
• Drive new client acquisition alongside organic growth from existing relationships
• Implement data-driven systems to predict churn and surface growth opportunities
• Work closely with the founder and leadership team on strategy and commercial outcomes

What You Bring to the Role

You've built your career leading customer success, sales, or a combined commercial function in a fast-moving business. You know how to hold teams accountable, read the data, and grow revenue from both new and existing relationships.

You'll bring:

• Senior experience leading customer success, sales, or a combined commercial function
• Proven ability to lead a team, set KPIs, and build accountability across multiple functions
• Data literacy, including working with pipeline reporting, churn prediction, and customer health metrics
• A commercial mindset with experience growing revenue through both new business and existing client relationships
• Comfort in a fast-paced, autonomous, founder-led environment
• Experience in professional services, B2B SaaS, proptech, or high-growth service businesses is highly regarded

What's in it for You

• Join one of the most respected and talked-about companies in real estate right now
• Real autonomy in a founder-led business where decisions are made quickly, and things get done
• Lead a growing team with a clear scope to expand across both functions
• A culture worth joining, high energy and results-driven, backed by a founder deeply invested in the people around them

Next Steps

If you've successfully built and led sales and customer success teams and you're ready to own something meaningful again, we'd love to hear from you. Apply now or reach out directly to start a conversation.