Why Australia's Top Real Estate Leaders Are Heading to the Philippines

As offshoring becomes a core pillar of real estate operations, Australian agencies are beginning to rethink how they engage with their remote teams.

For Wingman Group, this shift is more than operational – it’s deeply personal. 

Through The Retreat: Philippines 3.0, Wingman has created an annual event where over 600 offshore professionals within their contracting community and Australian real estate leaders come together — not just to collaborate, but to connect, grow, and spend meaningful time with the Remote Professionals powering their operations. It’s a celebration of partnership, performance, and shared purpose.

Now in its third year, the six-day retreat blends leadership workshops, cultural immersion, and recognition events — all underpinned by a simple but powerful purpose: to change lives in the Philippines.

“From day one, this retreat has been about recognising the Remote Professionals driving some of Australia’s top agencies — and using our platform to create real, lasting opportunities in the Philippines,” says Jonny Bell, Founder of Wingman. 

The event carries weight in the real estate industry, where offshore teams now play a critical role — supporting agents with marketing, admin, prospecting and more. Yet despite their impact, many remain unseen and disconnected from the businesses they help scale.

Wingman’s CEO, Jonathan Rostron, says that the company’s goal is to shift that paradigm.  “Wingman’s vision is to reshape the perception of offshoring. In real estate, trust and communication are everything — and that starts with truly knowing your team.

When you meet face-to-face, it breaks down barriers, builds loyalty, and creates alignment you simply can’t replicate over Zoom.”

For Wingman, the retreat isn’t a one-off gesture — it’s a living expression of the company’s core philosophy.

Their work in the Philippines is built on long-term partnerships, promoting flexible working conditions, and meaningful cultural exchange. It’s a model designed not just to scale businesses, but to do it sustainably and in support of their incredible offshore contracting community. 

The impact is twofold: Australian agencies gain stronger collaboration and lower turnover, while Filipino professionals receive real recognition and the kind of flexibility and benefits that changes families — and communities.

“Offshoring can be a race to the bottom, or a force for good,” says Rostron. “We chose the latter — and that means showing up, in person, and building something real.”

As offshoring accelerates in real estate, The Retreat: Philippines 3.0 represents a new kind of model — where connection, culture, and contribution matter just as much as cost and capability.