The Roofing Professionals Westside – The Premier Trusted roof repair service in Sydney

If you have lost faith in the Sydney roofing industry because every other roofer in Sydney who you have engaged have fallen short – then the team at The Roofing Professionals Westside will raise their hands to be your faith restorer.

Roof Repairs Sydney - roofer training
Training the best Roof repairers in Sydney

From humble beginnings repairing hail damaged roofs in 1999, Jack The Roofer has stashed away all those hard earned roofing secrets that has made him the ‘Go-To’ roofer of last resort who can pull off that miracle roof repair.

With a generosity in sharing his deep insights in the roof repair business with his team, a new generation of trained and trusted roofers have been unleashed into the Sydney roofing scene.

Jack developed the culture of ‘doing the right thing’ by Sydney homeowners and providing them with the roofing service that they deserved.

It is this culture that the Roofing Professionals Westside team is propagating as they re-define the Sydney roof repair game – one roof at a time.

Table of Contents

Roof Repairs may need an engineering degree
Seat D9 was vacant that day. Jack had other things more important to do.

Jack the Roofer in Sydney – An Introduction

Jack the roofer never turned up for his graduation ceremony. He had other things that were more important.

There are many things that Jack does that are not conventional. He is a bit of an OUTLIER. Who stashes a hard earned Engineering Degree in the back of a closet and starts a new career carrying roof tiles as a roofing labourer?

Jack did. The 1999 Sydney hailstorm was the turning point.

The challenge of repairing leaking roofs is the lack of suitable training. Jack had excellent training under the tradesmen he worked under. But this was in roof installation work. When he started playing the roof repair game – there was no trainer around. So, Jack had to learn everything from FIRST PRINCIPLES.

This was pioneering work.

Switching careers demands an intentional process of un-learning and opening up to learning things that are completely unknown. This is ‘ego destroying’.

That is why it took over a decade of mistakes before Jack got wise enough to have a roofing business that started to thrive.

Comfort in remaining at a certain level of success is the ‘killer’ of growth. Now in his mid sixties, Jack had to negotiate another cross road.

Languish, pull the plug, business sale or the unthinkable?

Roof Repairs Sydney 2001
Re-inventing roof repairers in Sydney back in 2001

Act 1: Re-invention

“If it ain’t broke, don’t fix it”

When there are thousands of hail damage roofs in the Eastern suburbs of Sydney in 1999 (and a shortage of roofers), demand exceeds supply. There was no need for any sales and marketing during that hectic period.

Every boom is followed by a bust.

And when the roofing bust came, every roofer in Sydney was looking for work. But, there was little work to go around.

When the phones stopped ringing, Jack was introduced to what a business is all about.

It doesn’t matter how good you are…if no one knows about your skill, there is nowhere to apply your expertise.

The Roofing Professionals had BRAND marketing that was shared by two separate companies – and while this type of exposure had some measure of success, it was not working much during the bust.

Was the marketing broken?


  • The message behind BRANDING:

There is always an “implied” message behind any branding promotion.

The Roofing Professionals was set up to be a brand. And this had enough value to entice potential business owners to actually pay money for. Initially 4 separate business owners bought into the brand.

Why was the brand strong enough to be worth those dollars?

There is an implied message that Professionals know what they are doing and are also willing to put “skin in the Game”. They back up their skill confidence with performance guarantees.

This implied message can be a big factor in any decision over a multitude of options.


  • Saying the unsaid:

The difference between real professionals and nominal ones is this: They deliver on their promises.

And it is equally important to be specific on what the promise is. Otherwise the delivery will not fit the expectation.

The majority hide behind the BLAME game. It is always someone else.

Product guarantee has been (and still is) the ‘elephant in the room’ for the Australian building industry. The industry knows that quality is an issue – but don’t want to do anything about it. That is why there are many government regulations to force building contractors to include warranties and insurances in their product offerings.

Short life cycles of builders have been used to circumvent the need to fulfil warranties that may be needed many years after product delivery.

Naturally, when Jack suggested that the Roofing Professionals should be ‘upfront’ on roofing guarantees, there was push back from the incumbents.

But Jack thought that if his business was to be around for a long time, then long duration warranties should be built into the business model. He persisted and Roof repair warranties became the up front commitment. Not just an implied byproduct.


  • The roof repair segment :

Everyone seem to think that playing in a ‘big pond’ yields the best opportunities. Jack was no exception and initially chose to operate in the general roofing industry.

He soon learnt that the ‘big fish in a small pond’ scene was more fun to play in. In the typical Kevin Kelly ‘Thousand true fans’ style, the ‘long tail’ was more suited to small players

And Jack was happy to be ‘small’ – and stay in the happy world.

The big commercial style of roofing work has big dollars against them – but they proved counterproductive. And just putting up new roofs in a super competitive segment turned out to be a ‘rinse and repeat’ rut – without diversity of complex learning.

Initially, Jack felt that the roof repair scene was just too much trouble. But that was because he had little expertise in the intricacies of leaking roofs. He began his roofing career having little idea of how to fix leaking roofs.

Working hard like every other roofer in Sydney on general roofing work is just – HARD. But working smart on challenging roof repair work offered a pivot. And the pivotal moment for Jack was when his roofers remarked one day:

Why is 80% of our work becoming just repairing other roofer’s stuff-ups?

While Jack is probably not the smartest kid on the block – he was smart enough to pick up on this nuance in Sydney’s roofing industry.. 

Roof Repairs Homebush Sydney
Roof repairs is a piece of cake when Jack is in the flow.

Act 2: Playing with skill

Have you ever had those periods in your life when you were in the flow and every challenge became an exciting obstacle to overcome? And this was the reward for getting to the next level.

This is what happened to Jack and his guys at The Roofing Professionals Westside. They tried things. Some worked and others were just rubbish. Then things started to work and they felt that they were almost invincible because they were operating at a completely different level to their past lives.


  • The unlikely benefits of saying NO :

There is a concept called ‘OPPORTUNITY COST’. And also a related concept called ‘SUNK COSTS’.

Focus is the key to mastery. Shining objects are distractions. Yet, the shining objects glint of treasure. And that is why Jack got mesmerised with saying YES to everything. Until it started to get in the way.

Trying to please everyone meant the cost of pissing himself off.

They say that ‘Less is More’. But saying is not believing.

One ‘belonging’ at a time, Jack let go. The big jobs (that got in the way of the small interesting roof repair jobs) were tidied up and never to be returned to again. Teams of roof installers were ‘let go’. Shop lease let to expire. Jack said NO to a lot of traditional roofing work – and even said No to answering his phone. And Jack re-organised his work to allow him to work from home.

All to bet on a future in the ‘long tail’ of roof repairs.

And it worked!


  • The daunting task of duplication:

An ‘intergenerational’ team allows for transfer of culture and skills amongst its members. Jack had attracted Gen X and Gen Y into the roof repair team who were keen to make things happen. But skill transfer comes with some costs. Roofers joined the team, learnt some of the important basics – then left to become their own bosses.

However, ultimate skill takes patience and time to acquire. No one else seemed to be able to grasp this requirement before they left.

How to create clones of Jack?.

Easy in theory – but it practice, it was looking like an impossibility.


  • Levelling up – what playing on the next level means:

True knowledge appears when one is able to teach the subject successfully. Jack discovered that there were massive gaps in his knowledge and skill when he tried to train his roofers. Staying at his comfortable level was like living in an echo chamber where Jack was just happy to believe in his own BS.

To move up to the next level of skill, required killing his ego. Only then could he move up.


Roof Repairs Sydney finished roof
Roof repairs – the finish line is a well functioning roof

Act 3: The finish line

Most business plans have an EXIT component. Create, build, add value, and finally sell.

The other Roofing Professionals business in Sydney had executed on its exit plan. And it was time for Jack to do the same.


  • The END is not the finish:

When a day ends, life hasn’t finished. Even though darkness descents, this period is meant for rest, rejuvenation and growth. Then another day begins.

Just as when an athlete crosses the finish line, it means another round of training and another competition.

For Jack, selling his business meant the end of continuity for his clients. He had promised them years of warranty coverage. How was this to be fulfilled?


  • Keeping the promise:

Our enduring religions have a way of keeping the promise alive. The gospel is spread by its prophets.

Jack’s solution to keeping his promises was to create continuity by growing the next generation of independant prophets who carry the business into the future.

To keep his promises, Jack had more work to do…

Roof Repairs Sydney finished roof
Roof repairs Sydney- continuing the legacy through The Roofing Portal

Act 4: The journey continues.

Jack came up with an idea.

What if he offered the cream of his employees the chance to do something BIG and enduring for their futures? A chance to start their own businesses to become Jack’s prophets…


  • The business of the future:

The last few decades of exponential growth on this planet has been facilitated by one phenomenon.


The railway. Phones. Faxes. Social Media. Uber. Airbnb.

The Network effect created all this. Connection is the business of the future.

So Jack told his new business partners that the new roofing business had to be built for the future. And using the phenomenon of the Network effect was essential.


  • The Uber Model applied to roofing:

Multitudes of cars parked up under utilised. And they all have drivers who know how to drive (although you can argue that the ability to drive lies on a spectrum). Uber was born and overtook the taxi industry.

The rise of the GIG economy is paralleled by the the independant contractor growth in the building industry. So, thousands of independant roofing operators – who know how to roof (also on a spectrum). And most of them scratching for work.

Makes for an opportunity to apply the Uber model to the roof repair industry?


  • The Insurmountable Obstacle:

“If you think driving is a complex skill – try fixing tricky roof leaks”.

If it was easy, then it would have been done. The big difference between drivers and roofers is the skill level that is required to perform the required tasks – with minimum feedback.

Drivers get instant feedback if they wander off their lane, cut another off, overspeed and disobey traffic rules.

Roofers do not. Their work is not usually critiqued by their peers. So, they can get away with unskilled roof repair work without the critical ‘feedback’ loop.

And the result is BAD culture combined with underperforming skills.

It is a cesspool of roofers to try to draw from. This is the obstacle to duplicating the Uber model across to roof repairs.


  • The role of the scout:

“Get to know the territory – before the main force moves in”.

Jack’s new business venture (in partnership with the right individuals), is to scout the Building Industry for the viability of using the Uber Model. Starting with the roof repair segment (which he knows in intimate detail), it will be a long JOURNEY.


Then ?

Roof Repairs Sydney contractor licence
It is just a licence. the difference is what is behind the licence

The Legal stuff – What you may need to know

Now that you know the real story ABOUT US.

You may also want to know about the regulatory stuff.

Much like an FAQ, it is just a click to expand each section. It may not be as exciting as our story – but it may be the final pieces of the puzzle that you need to make your decision about Jack and what he is trying to do.

And whether to support him or not. 

How long have you been doing roof repairs in Sydney?

I started roofing work in 1999 and learnt ‘on the tools’ for a few years before facing the big challenge of operating a roofing business that is successful enough to remain solvent for the long term.

I am hardly on the tools any more. I have trained my roofers to be better than I am at repairing roofs. Now, I just make sure that there is continuity in the business to honor my on-going warranties…

Read more about Jack The Roofer Story

Why don't you have telephone numbers?

The telephone is mankind’s ultimate attention destroyer.

You are in the middle of something important and the phone rings. Most people pick up. Slave to the interruption rather than sticking with the flow.

I forced myself to put my phone on silent – so that I could be more productive. That was 10 years ago. I killed the Fear Of Missing Out.

For most of my day, I don’t answer my phone – so giving you a phone number will only frustrate you. If I get another person to answer my phones, I only get more messages than I can cope with. Which means that messages get unanswered. That is not good.

In the last 10 years, nothing ‘BAD’ has happened because I did not answer my phone. I am safer letting my phone ring out than stopping in mid-stride to take a call. I am on the road driving , or on a roof for most of my day.

I do have an office phone at our new warehouse location and it is 02 8376 1451 (but we do not have a receptionist – so you may need to leave a message for us).

My mobile is 0416 264681 (you can text of leave a message).

The best way to get my attention is via email – and the only way to get my email is to fill in the CONTACT form on this website. Reaching out to me this way has a better chance of my attention because all the details go into my computer database. I tend to forget things as soon as I hang up the phone.

How are you associated with The roofing Professionals Eastside and Northside?

The 3 operating ‘The Roofing Professionals’ companies are all independently owned. There is currently very little relationship between the Westside, Northside and Eastside companies.

Boris lives in Eastern Sydney and he owns and operates The Roofing Professionals Eastside.

Brad lives up the coast and the owns and operates The Roofing Professionals Northside.

From very interesting beginnings, the ‘Roofing Professionals’ brand has come a long way…

What are your company registration, ABN and insurance details?

The Roofing Professionals Westside is a business name registered with ASIC.

The Roofing Professionals Westside is owned by a registered company called ADVCON Pty Ltd.

ADVCON Pty Ltd is GST registered and holds ABN 35 072 196 411.

This means that The Roofing Professionals Westside is registered for GST and it’s ABN number is also 35 072 196 411

ADVCON Pty Ltd has Workers Compensation cover with ‘ICare Workers Insurance” (Policy number 117390201)

and Public Liability Cover with “Chase Underwriting P/L” (Policy Number 496729)

ADVCON Pty Ltd Contractor Lic 2026

The Roofing Professionals Westside business name registration

We do not take any money upfront.

We do not take any money upfront.

We do not take any deposits if you accept our quote and want to book a roof repair job in. (there is a reason why we do this and you can go to the Roof Repair work deposit page if you want more information).

We will generally email you an invoice when all the work as quoted has been completed. This invoice will have EFT banking details for you to pay us.

Who physically does the roof repair work?

We have a team meeting every morning to decide who is best suited to do the different roof repair jobs that are scheduled that day.

The tricky jobs will go to the more experienced workers. We have one apprentice and a few tradesmen. The experienced tradesmen are contractors in their own right.

The good roofers that I have trained up generally want to be independent (with my complete blessing) and they are free to come and go. But these roofers retain our core culture of playing the ‘LONG GAME’. Jobs are not complete until the solution is permanent.

I do not ‘handle the tools’ much nowadays. My roofers can do a far better job than I can.

Besides, I am busy making sure that my roofers have a good future, by getting them suitable work – since we are all playing the ‘long game’.


Or, you can easily continue your journey with us to The Roofing Portal by booking an appointment below:


Otherwise, you can go back to our HOME PAGE.  

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9 years ago

Need you to replace a roof in rozelle.

9 years ago

building a new duplex in Yagoona, require a quote for all the roofing work

9 years ago

Hi jack,
Would you repair leaks from roof tiles probably due to cracking sealants?

Alastair Wylie
Alastair Wylie
6 years ago

Hi Jack
At the corner of our gable end the eaves have dropped slightly and separated from the barge board. I think this is a remnant of the big storm we had in 1991 but has only happened recently. The roof itself looks ok. Is this the kind of repair you can do? Thanks, Alastair, Normanhurst

6 years ago

Hi Jack, we have a flat roof with a leaking skylight & have been back and forward with AAMI for 8 months or so, after the skylight cap was replaced following a hail storm. It was not leaking prior to the man going up and hammering at the skylight. Anyway, long story short, we would like to remove the skylight and bitumen roof covering and replace it with Klip Lock roofing. Are you able to give us a quote to do this?
Many thanks, Jane