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Have You Met Melbourne’s Jacky Winter?

The Jacky Winter Group, 2 years, 6 months ago

How one lone New Yorker in Australia turned his zest for illustration into one of the world's most in-demand artist agencies

Have You Met Melbourne’s Jacky Winter?

Not a person, plane or bird, Jacky Winter is a creative service agency with its roots in specialist production. Launched in 2007 by New York expat Jeremy Wortsman, what started as a one-man band representing a rustled-up crew of 12 illustrators, has turned into a whiz-bang production team who rep over a hundred diverse image-makers crafting from remote nooks and crannies the world over. 

Evolving from the confines of his bedroom to a team of 10 working out of a designer dreamy studio in Collingwood, Melbourne, came down to a little bit of luck and a lot of hard work. That said Wortsman has always stuck to a simple formula of representing artists who set his heart a flutter. In many ways, he considers the agency to be a very honest representation of the overlap between his own personal aesthetics and the tangible commercial needs of his clients. Coupled with a self-confessed and inbuilt need to be of service, he says nothing feels as good as making connections between people and recommending great talent and artists.

“When a brief came through in the early days, that we might not have had the perfect artist for, I went out and found that artist and developed the relationship and brought them on board,” he said. “I took a lot of personal pride in providing a premium service that clients valued, and that opened up bigger and bigger conversations that were all based on a mutual trust that we would deliver.”

Through this repeated process, Wortsman effectively built a business for his clients and at the same time has been able to support and sustain the careers of over a hundred artists. “It's been a pretty great ride so far!” he hinted.



Jacky Winter’s home turf has always been and still is illustration, with wings dedicated to particular disciplines. From a classical digital painter through to a 1940s movie poster designer or a fine artist based in the rural south of China, you name it and Wortsman’s got a creative to match the job in mind. 

While the agency is shifting towards a broader spectrum of image making to open up new avenues for exploration, illustration definitely makes up the bulk of represented talent. “Illustration in particular is having a major golden age and renaissance as more brands realise that they can really capture the subtleties of their products and services through illustration,” he explained. 

“I think the medium as a whole just taps into something really raw and primal in terms of how human beings communicate, while at the same time it is very much of the moment, from comic books to street art.”



More than any other medium, Wortsman argues that illustration allows for so much more nuance and an ability to capture a huge range of expressions and emotions. “Put the right art director together with the right talent, and you can really develop something truly new, which is becoming harder to do these days in other forms and industries. I think this fact makes it very attractive to brands and advertisers because it allows them to really stake their claim in these new territories.”

In today's landscape where attention and time come at a high premium, he said illustration is one of the most effective ways to achieve cut-through and to really 'own' a look and feel. “Even more so when we are looking towards the future of increasing video content and motion graphics, illustration only going to open more opportunities for creators and clients alike,” he added.

Catering to the varied needs of clients today, Jacky Winter has different subsets including The Perch, The Hatch and Rock of Eye. The creation of these subsets, Wortsman says, is a natural extension to the agency’s growth and has allowed the team to really focus on a strategy that allows the business to grow without alienating its existing artist or clients, or spreading the team too thin.


“For example, when we started out, there were some great clients out there who had pro-bono or charity briefs that we really wanted to help them with, but they didn't suit the core group of established talent that we had on board. This was the foundation for our first 'branch' of the agency, The Hatch, which represents more emerging artists. It was a similar situation when clients started coming for storyboards and visuals, and so The Bowery emerged.” 

Later on, it allowed Jacky Winter to make much more significant branches through partnerships and alignments, such as its photography branch, SEA, and its animation division, Flutter. The separations are a useful tool for the agency as it allows it to stay relevant in its communications and defined in presenting the right group of creatives for the right briefs, while at the same time really allowing Jacky Winter to expand its offering to take on pretty much any brief under the sun.

The bulk of Jacky Winter’s international clients are in The States and the time difference can often work in everyone’s favour. The agency has strong foundations in terms of the processes used with its online collaboration system and depending on the exact location of clients, Wortsman says producers can typically manage communication during everyone’s same business hours.  

“Once a job gets rolling, we can effectively work on a 24-hour production cycle. When we are sleeping, the client is circulating the work and gathering feedback. We address feedback and develop it along when they sleep, and it just keeps rolling with minimal downtime.”  


Depending on the currency exchange rate, location can also allow the agency to be financially competitive, especially as U.S. budgets are typically more generous considering the higher value placed on work in the States due to the larger population and corresponding media buys.

Not simply a traditional rep (that pairs creative with client and sends an invoice at the end), Jacky Winter is known to be an active collaborator in the creative process. Whether it's negotiating a contract and royalty agreement for a book series, or rolling out an integrated national campaign across a minefield of deadlines and stakeholders, the agency draws on its collective experience to make the commissioning process as painless as possible, for artist and client alike.

“Our whole process starts with promotion. We are very active in marketing our artists to the industry both domestically and internationally and we push ourselves every day to innovate in that area to make sure that everyone's work is reaching the right pairs of eyeballs, and that our marketing material is actually contributing something useful to people in the industry.”

Jacky Winter produces beautiful print publications, maintains an active social media profile, runs events and maintains a gallery space, Lamington Drive. “It all comes back to raising the profile and reputation of the agency, which all our represented talent benefit from and at the same time contribute something positive to the industry.”

Once a job is underway, the agency’s biggest asset for talent is ensuring their work is valued and licensed appropriately, while at the same time balancing the clients’ needs and constraints with regard to budgets, deliverables and timelines.

When not in production or promotion mode, Wortsman and his team actively seek out new areas to grow the business, progress the careers of artists, and simply find new opportunities to start the cycle all over again.

“We occupy a very special place in the creative process and our role as producers can range from being a translator on one day, to being a life coach or therapist another day – it's an incredibly demanding yet rewarding role. The bottom line is that we get the right mix of people, processes, and creativity working in harmony to get things done and make everyone look good.”

When it comes to working in the Melbourne industry, the pull of the city’s cultural validity is what attracted Wortsman from his birthplace in New York over 12 years ago.

“Something about the bad weather definitely has something to do with making great creatives. If I lived in Sydney, I know I'd just be at the beach every day! There's something about cold and grey climates that I think makes people stay indoors and become artists.” 

Although he admits the best string to Melbourne’s bow is its distinctive balance. 

“Melbourne is one part LA, and one part NY. A little bit of Europe mixed with a little bit of Asia. Throw it in the pot, and you have an incredibly potent brew, which seems to attract some of the brightest minds both domestically, and internationally. I think we're only starting to see the results now.”


Jacky Winter is running a conference in Sydney called Jacky Winter Gives You The Business

Genre: Illustration