When David Highland launched Highland in 2007, it was a small, close-knit team in Sydney’s Sutherland Shire. Since then, the company has evolved into a thriving independent network of eight offices across the East Coast, with a presence in markets including Double Bay, the Inner West, the Southern Highlands, the Northern Rivers and the Gold Coast.
Under his leadership, Highland now transacts more than $2 billion in sales each year.
Between 2021 and 2024, Highland onboarded five new offices and completed a major acquisition as part of the group strategy – Calico Marina in Cronulla in 2023.
This was followed by the launch of Highland Marine in 2024 that is a fully fledged boat brokerage arm for the group that operates from the marina.
It was an ambitious growth period, but as David explains, the secret to scaling successfully is not speed, it’s control.
“Everything we do is about controlled growth,” he says.
“We’re always thinking six months ahead … what our needs will be, how our systems will handle it, and whether our people are ready.”
When Highland merges with a new office, the groundwork begins months in advance.
In April 2023, for example, the group partnered with the Kallin family in Newtown, adding about 30 staff and a rent roll of roughly 1,000 properties.
Before the merger, the leadership team carefully mapped what resources would be needed, from photographers and marketing associates to finance and operations support, so capacity was in place from day one.
That careful planning has allowed the company to expand quickly without losing its structure or culture.
In just 12 months, Highland onboarded seven new rent rolls in a rapid expansion that required scalable systems and strong leadership to keep everything moving smoothly.
Growing against the tide
David’s approach to growth is often countercyclical. During a two-year stretch of rising interest rates and weak consumer confidence, Highland was in acquisition mode rather than retreat.
“We grew exponentially during a challenging 24-month period,” he says. “We took advantage of a market that was hard for smaller operators. It wasn’t risky – it was strategic.”
Highland’s strong balance sheet coming out of the COVID years meant the business could move decisively when opportunities appeared.
“We leveraged our performance from that period to build scale,” David says. “It gave us more stability and cost efficiency in tougher conditions.
To manage that pace of expansion, the agency invested heavily in technology.
The company implemented modern CRM systems and launched the Highland Digital Platform to reach a broader yet highly targeted audience for property listings and it also adopted an AI chatbot to handle a high volume of customer inquiries around the clock.
Behind the scenes, the property management division has been transformed through new bespoke software that streamlines property onboarding and automates key workflows.
“We’re only at the beginning of the AI conversation,” David says.
“But we see it as something that will make people’s roles more efficient, not replace them. It’s about speed and quality.”
Building culture as you build scale
While technology underpins Highland’s operations, David believes the company’s strength lies in its people.
“When you walk through our head office, you’ll see people who’ve been with us for 10 or 15 years,” he says.
“Three of the original six staff from 2007 still work with us in some capacity. That’s what culture looks like.”
Highland’s leadership team is largely female, with many promoted from within. Training is constant and customised; from sales scripts and dialogues to leadership development and property management up-skilling.
Career progression is deliberate, David says, and as a result, retention is high.
Workplace design is also part of the equation. The company’s new 700-square-metre head office, five years in the making, was created to feel more like a high-end residential space than a corporate one.
“We want our people to enjoy coming to work,” he says. “When you invest in your environment, you invest in your team.”
Ownership that drives engagement
Another element of Highland’s success is its shareholder and equity model, which gives top performers real ownership within the business.
“It’s not just for salespeople,” David explains. “Our CFO, who’s also a founder, is a partner across all the offices. But we also have agents who hold equity in one or more offices.”
The model evolved into a joint-venture structure after Highland merged with Bill and David Malouf.
“It’s a true partnership,” he says. “We handle the back end, while they focus on the front line. Everyone stays in their lane, and it works.”
For ambitious agents, David says this approach provides an alternative to setting up independently.
“Why take on the cost and risk of running your own office, when you can be an equity partner, focus on what you do best, and share in the success of the business?”
Highland’s next phase is about consolidation rather than expansion for expansion’s sake.
After several acquisitions in the first half of the year, David’s focus is now on embedding systems, teams and technology across the group before taking the next step.
Future growth will remain concentrated in Sydney and South-East Queensland, in what David calls “relevant markets,” which are essentially blue-ribbon areas where the brand’s existing strengths can add value.
“The big players are getting stronger and the smaller agencies are merging,” he says. “That’s the direction the industry is heading. But for us, it’s not about being the biggest; it’s about growing in a way that’s sustainable, strategic, and true to who we are.”
Finally, for David, scaling successfully is about more than numbers. It’s about timing, readiness and balance.
“If you’re not growing, you’re going backwards,” he says. “But growth only works when it’s controlled.”
