With a career that began with selling discount vouchers, was interrupted by a vicious dog attack, and was inspired by a drunken buck’s night conversation, John Winning’s path has certainly been dotted with unexpected twists and turns. However, he’s definitely grown from the reluctant teen forced to work in the family business to one of the most unconventional yet successful businessmen in Australia.

For someone who had no intention of ever becoming an executive, John has enjoyed his fair share of success. He was the most recent recipient of The CEO Magazine’s Executive of the Year – Retail award, his third time winning the accolade since 2013, along with being presented with the Young Executive of the Year award in 2012 — all before his thirty-third birthday. Wind back the clock, though, and a teenage John is waiting tables at Doyle’s restaurant in Sydney’s Watsons Bay, studying for a coxswain’s ticket to support a potential job operating water taxis, and dreaming of being a professional photographer. 

John Winning on joining the family business

His father, also John, is a third-generation retailer and former CEO of Winning Group — a leading kitchen and laundry appliance specialist and family business. Open to all possibilities, John sees a job advertisement in the paper for a direct-marketing role (no experience required), and dreaming of a shiny Mad Men world of fun and creativity, he jumps at the chance to enter the marketing arena. “I quickly worked out that ‘direct marketing’ meant knocking on doors and selling vouchers for video shops and pizza places,” says John.  

John Winning, Group CEO of Winning Group
John Winning, Group CEO of Winning Group

“I thought, ‘This isn’t what I signed up for,’ but I did a day trial and it worked out that I actually didn’t mind it at all. It was door-to-door sales, and I loved it. It was probably where I became addicted to hard work because you do work hard when it’s 100% commission based.”

After a year of charming potential customers at their doorsteps, John’s first sales gig ended abruptly at the age of 19 when he was attacked by a dog on the job. “I ended up in hospital after that, and my dad said to me, ‘Is this really what you want to be doing? Because I suggest you don’t do it anymore’,” John explains.

“Once I came home, he gave me the option of finding another job by Monday, or I had to go to work with him.” True to his word, when Monday arrived for a still-unemployed John, his dad woke him up and took him to the Winning Group warehouse to start work with him. “At that point, I didn’t want to join the family business — I always thought I wanted to do something else and pave my own path — but all the same, I started working in the warehouse, and not too long after that I was driving trucks and doing deliveries.”

Developing the Winning skills

John’s door-to-door selling days were not time wasted, however, with many crucial skills he picked up later leveraged in his work as a retail executive, and some he had to learn the hard way. “Being attacked by a dog is just one of the many colourful stories I have from working with that business,” John says. “People don’t love you knocking on their door at night, I can tell you. Some of the verbal abuse was up there with the dog attack. But you learn to be thick-skinned and you certainly learn the trick of selling and quickly getting to the point.”

Line honours champagne spray

“I am lucky enough to sail with and against some of the best in the world and I really love it when I am out on the water.”

John has also developed skills around working in a team in unconventional scenarios from his love of sailing — more than just a hobby for the expert sailor who won the World Championships in the 29er class in 2002. “I love the ocean. I grew up in a sailing boat, so the water is part of me,” says John. “My grandfather sailed, and my dad is also a former world champion. I’ve sailed for as long as I could walk, and was involved in boat racing by the age of 4, so definitely before I could swim anyway.”

John even recently took part in the 2016 Sydney to Hobart Yacht Race as part of the record-breaking and line honours winning team for Perpetual Loyal. “I don’t sail as much as I used to, but it comes naturally to me now, so I don’t have to sail every weekend just to be able to do it. I am lucky enough to sail with and against some of the best in the world, and I really love it when I am out on the water.”  

Launching Appliances Online

John’s retailing success took off after a realisation he made while working in the Winning Appliances’ clearance and Redfern-located stores. A lack of real footfall saw him begin considering more efficient ways to make sales.

Perpetual Loyal

“I kept thinking to myself, ‘Our stores are a bit of destination; they’re not in the high-traffic areas,’ and we weren’t getting many people coming that far out for a clearance washing machine. So I was constantly thinking about how we could be better at that,” John says.

At that stage, many big retailers had been putting out printed catalogues, but John ended up going one step further and launching one of the first online listings, appliances-online.com.au. “It all started with entrepreneurial thinking mixed with advice from friends and a bit of luck and timing,” he says.

“While at a buck’s party, I spoke to a great friend of mine from America, Matthew Hyder. We were leaving this party, both inebriated and arm-in-arm, talking about what the future holds. He said to me, ‘John, you’ve got to get online. I’m watching it in America: e-commerce is just starting to happen and no-one is doing it in Australia. The internet is the next big thing; get your products online.’ Matthew planted the seed, and the idea took off in my head. The more I thought of it, the better it seemed.”

Overcoming resistance & building the site

The idea of having an online, up-to-date catalogue that could hold all their products and that didn’t require the added costs of printing and distribution was something John had to pursue, although he faced some resistance at first due to how little people knew of the internet.

“I don’t think I even had email at the time, and my dad has never been into technology. But I knew that it had legs and that it was a skill I must learn,” he says. “At first my dad said, ‘I don’t think it’s a good idea. I don’t think it’ll work. What’s the internet?’ He still doesn’t have an email address and he has never owned a computer. 

“He slept on it, though, and he spoke to the general manager at the time about it. He figured that since he forced me into the business, he didn’t want to shut down my first idea, so they decided to give me a chance.” From there, John approached the only person he knew who had any affiliation with the internet at the time — his friend James Fleet, who worked for a New Zealand-based digital agency — who said they could make it work.

“We commissioned this New Zealand company to build the site just because I knew the person who was working there and trusted what they said. Then I went on a personal journey to learn as much about e-commerce, marketing, and the internet as possible,” says John.

Overseeing the Winning Group

Since launching Appliances Online in 2004, key milestones for John were the day it took 10 orders in 24 hours, then the day it took 100 orders, to then 1,000 orders per day, and then when they opened the company’s first interstate distribution centre in Victoria.

“From there, almost every state that we entered was incredible,” says John. “We do a better job today than when we started 14 years ago, and to think that you can do a thousand orders better than you can do 3 is quite an achievement. That’s one of the things I am most proud of.”

With his father stepping down from the head role in 2011, John has been serving as the new group CEO for the whole of Winning Group, including Winning Appliances, Handy Crew, Home Clearance and Appliances Online. 

John Winning, Group CEO of Winning Group
Since launching Appliances Online in 2004, key milestones for John were the day it took 10 orders in 24 hours, then the day it took 100 orders, to then 1,000 orders per day, and then when they opened the company’s first interstate distribution centre in Victoria.

“We have managers within our business, including myself, who are happy to walk past the reception desk with the phone ringing, pick it up, and deal with a customer complaint.”

Growth at breakneck speed

He has seen the company go from a Sydney-only retailer to expanding into Victoria, Queensland, Western Australia and the ACT. “I am very proud that I could take over the 100-year-old family business and see significant growth through expansion and acquisition,” says John. Due to the breakneck speed at which the company began to grow once Appliances Online took off, John explains that he had to quickly adapt into a leadership role, which he did entirely on his own gut feel, rather than undertaking any leadership courses or even reading books on best practice. 

“I am now an unconventional leader because I don’t know what normal management is. I was thrown in the deep end because the business just grew. I went from being a kid that had done truck deliveries and a few sales on the shop floor, into suddenly running an e-commerce website when I knew nothing about technology, management or even retail, other than the fact that it’s in my blood,” says John. “It wasn’t until 5 or 6 years ago that I started reading books on this stuff, so for probably 8 or 10 years we had a really weird, unconventional structure where we all just chipped in and did our best.”

Not a traditional business

Despite its less conservative style, John says it has all worked out very well for the business to have different roles and responsibilities from what you’d normally see, including sales people who do their role well without being paid commission, a Team Experience team to replace the traditional HR department as a more positive and supportive environment for his employees, and executives who are happy to take customer complaints directly. 

We have managers within our business, myself included, who are happy to walk past the reception desk with the phone ringing and pick it up, and deal with customer complaints. - John Winning, Group CEO of Winning Group.

“We have managers within our business, myself included, who are happy to walk past the reception desk with the phone ringing and pick it up, and deal with customer complaints. All of our senior executives will receive 2 lots of negative feedback from our customers per week, and we have to call them ourselves and find a solution,” he says.

“In traditional business, there would be a department that deals with that stuff, but we want to make sure that we always stay in touch with the customer. To me, there is no-one more accountable for problems than the execs, to be honest. It’s absolutely critical so that we don’t forget why we come to work. It also helps us to stand by the mistakes together as a team.”

Creating a valuable internal culture

One of the best things he has ever done, John says, is to put together his team of 600, who have helped him to create the internal culture he has grown to value so greatly, and which produces the best results for his customers. Whereas once the company was expanding so rapidly that newcomers would simply be handed a phone and told to get cracking, today John ensures that all recruits are exposed to a thorough 3-week induction process that sees them introduced to all aspects of the business, rather than just their own remit. 

“We want people to understand all the moving parts of the business and their nuances: you do deliveries, you spend time in the warehouse, you do time in our physical stores, you work the phones and deal with online orders, you work with the marketing teams, administration, accounts, technology, and so on,” says John. “You learn everything about our business from start to finish, with a half-day or a day in each department, so by the time you start in your role you know who people are, what the business does, and where the parts fit together.”

The Winning Group is focused on its own race

When discussing strategy, John says the company prefers not to focus on what the competition is doing, thinking instead only of their own race and how to keep moving faster and stronger.   

“I like to use the analogy of being like a race horse that wears blinkers to stop it looking to the side or rear so they can just focus on their race,” says John. “People often ask me what the competition is doing and I truly don’t know. I can’t remember the last time I visited a competitor’s website, because I am talking directly to our customers. I have my blinkers on.”

The customer-centric approach was strongly instilled into John by his dad, who has always believed no matter what, the customer is always boss. “We look inwards and ask: Who are the people that have bought from us for the past 10 years? Let’s talk to them about where they want to see us, because who better to set our strategy than the people who are spending the dollars rather than people hidden away in a boardroom.” 

The strategy seems to be working, as the company’s Net Promoter Score (currently >75) continues to improve no matter how big it grows, reinvesting its profits into improving the company, its service and offerings, including larger ranges of stock and better technologies. John’s mission is to provide the best shopping experience in the world — which, coincidentally, saw Appliances Online win the award for Best Customer Experience for any retailer in the 2013 Oracle World Retail Awards. 

“We’re very proud to have been able to achieve our mission — but that doesn’t mean that we don’t wake up the next day and continue to strive to be better,” says John.  

You can download the PDF version (as seen in the magazine) below...