The engine behind the standard: Meet Tess Pitcher

Some people build businesses from the front.

Others build what makes them work.

Tess Pitcher does both.

It started with a ten-minute interview

Founder of Pilot Hill, Kristy McGrath and Tess Pitcher were meant to meet at a café.

Tess Pitcher, General Manager: Pilot Hill

It was supposed to be a simple conversation about a small, four-hour-a-week virtual assistant role.

The café was closed.

So they went to the pub instead.

One glass of wine. Ten minutes.

“That was it,” Tess says. “We both just knew.”

What started as a small support role quickly became something much bigger. Because from the beginning, it was clear Tess wasn’t there to assist the business.

She was there to help build it.

Long before Oceanstays, there were systems

Tess didn’t come from traditional property.

She came from business.

She grew up in a family-run business, then went on to run her own. But the defining chapter came early.

At nineteen, she was managing four McDonald’s stores.

“That’s where everything changed,” she says. “You don’t manage that kind of volume without structure. You learn very quickly that if the systems aren’t right, nothing works.”

It wasn’t just about keeping things moving.

It was about building systems that endure, recruiting people who can perform under pressure and creating consistency at scale.

That discipline has never left her.

Bringing rigour to property

When Tess stepped into Pilot Hill, she saw something different.

Beautiful homes. Incredible locations. Strong demand.

But like much of the industry, too much was left to chance.

“A lot of people think property management is about being handy or local,” she says. “But when you’re managing a premium coastal asset, it’s about the strength of your systems.”

Today, Tess leads the operational engine behind Pilot Hill, ensuring every property is managed with consistency, discipline and intent.

Great people

Firm processes

Continuous improvement

That’s the foundation.

The impeccable reset

At the centre of Tess’s approach is what she calls the “Impeccable Reset”.

Every stay is treated like the first.

Every detail is deliberate.

Because consistency doesn’t happen by accident.

“We don’t leave cleanliness or maintenance to chance,” she says. “We train our team to follow a proven blueprint. If the process is right, the experience is predictable.”

And predictable experiences lead to something powerful:

Trust.

Reviews.

Repeat bookings.

Which ultimately drive performance.

Culture is the real advantage

For Tess, systems are only part of the equation.

People are what bring them to life.

“You can have the best house on the coast,” she says, “but if you don’t have the right people looking after it, it won’t perform.”

Her focus has always been on building teams that care about the outcome.

Not just completing tasks, but understanding why they matter.

That shows up in how the team is trained, supported and empowered.

There’s no hierarchy for the sake of it. No distance between leadership and execution.

It’s hands-on. It’s coached. It’s continuous.

“We don’t just do the job,” she says. “We look for ways to do it better.”

Protecting the asset from the inside out

While Kristy focuses on strategy and growth, Tess ensures the engine never misses a beat.

She works closely with owners to optimise their properties from the inside out.

Refining processes

Improving efficiency

Maintaining standards

Day in, day out.

Because performance isn’t just about attracting bookings.

It’s about delivering, every single time.

The quiet force behind it all

Tess doesn’t seek attention.

But her impact is everywhere.

In the consistency of the homes

In the strength of the team

In the systems that hold everything together

She is the reason the standard holds.

And that’s the difference

In an industry where many properties are passively managed, Tess brings discipline.

In a market where experience can vary, she builds consistency.

In a business built on people, she empowers them to perform.

“I’m here to make sure the engine behind your holiday home never misses a beat,” she says.

And it doesn’t.