Jon is a seasoned outdoor media professional with a sharp eye for high-performing billboard sites and a genuinely Jolly approach to working with business owners and landlords alike.
With extensive experience owning and working across multiple billboard and digital media companies throughout New Zealand and Australia, Jon saw first hand how legacy operators were overcomplicating – and overpricing – outdoor advertising.
Jolly Billboards was born from a simple idea: make great billboard sites easier to buy, more affordable, and far more enjoyable to deal with.
Today, Jon leads a full-service team delivering nationwide billboard solutions, including direct sales, programmatic opportunities, and seamless support for both advertisers and agencies. Get in touch and we’ll connect you with the right Jolly person for the job.
With more than a decade in media sales, Jack knows the industry inside and out. He’s built his reputation on straight-talking advice, honest strategy, and campaigns that actually deliver results.
Jack works closely with both advertisers and landlords – helping businesses build smart, effective billboard campaigns, and turning quality sites into high-performing income assets.
He’s known for being likeable, authentic, and refreshingly transparent. If he doesn’t believe a site will work for you, he’ll tell you.
Outside of work, Jack is a proud dad of two and partner to Hannah. He enjoys a good pint and the occasional punt, and brings that same energy and competitiveness to delivering results for his clients.
Caleb may be the youngest member of the Jolly team, but he’s already making his mark.
Originally from South Africa, Caleb joined Jolly Billboards after completing his degree at Victoria University. Working closely with Jon, he’s quickly building a strong foundation in outdoor media, sales strategy, and campaign execution.
Caleb brings energy, care, and a genuine willingness to do the hard work. He’s detail-focused, proactive, and determined to get results for clients — whether that means digging into the data, supporting campaign rollouts, or going the extra mile behind the scenes.
He’s proof that great salespeople aren’t just born – they’re built.
Jude brings extensive experience across New Zealand’s media industry, with a strong reputation for being hardworking, detail-focused, and deeply committed to her clients.
She has worked across multiple facets of media and understands how to structure campaigns that make sense – especially when navigating complex or nationwide buys. Jude has a particular strength working alongside advertising agencies, where her organisation and clarity make even the most layered campaigns feel straightforward.
Clients value her steady, hardworking ethic and her genuine drive to go the extra mile. When Jude says she’ll take care of something, she does.
Outside of billboards, Jude’s other great love is dogs – and she’ll happily talk about them at length if you let her.
With over a decade in broadcasting and media (including 10 years with MediaWorks) Sam brings serious storytelling and audience expertise to Jolly Billboards.
A University of Canterbury graduate, Sam understands both the strategy and the craft behind strong content. From on-air broadcasting to co-hosting a successful podcast, she knows how to build connection, shape narratives, and create content that people actually engage with.
At Jolly, Sam leads content creation, marketing strategy and social media. Resourceful, quick-thinking and highly adaptable, Sam thrives on turning ideas into action and bringing a touch of Jolly energy to every campaign.
Outside of work, she’s also a proud mum to a busy three-year-old – a role that rivals any media deadline.
Mel is the glue that holds Jolly Billboards together.
From administration and accounts to production and campaign coordination, Mel keeps the wheels turning and the details tight. Her background spans startups and corporate enterprises, giving her the ability to balance agility with precision.
She’s known for her organisation, her reliability, and yes – her genuine love of a good spreadsheet. While that may not thrill everyone, it’s exactly the kind of energy that keeps campaigns on track and clients confident.
A mum of four and Jon’s partner in both business and life, Mel brings calm capability to everything she does.
Wellington born and bred, Michelle joined Jolly after nearly 15 years with Rangahau Aotearoa Research New Zealand, bringing calm capability from a world where details really matter.
Working alongside Mel, Michelle helps keep the administrative and production side of Jolly humming. Whether it’s making sure campaigns are ready to roll, logistics are sorted, or the small but important things don’t slip through the cracks, she’s already become a trusted part of the Jolly team.
Hardworking, quick to pick things up, and always happy to get stuck in, Michelle brings a steady hand and a positive attitude to the team.
Outside of work, she’s a keen reader, an enthusiastic baker, and proudly considers herself a bit of a shortbread and gingernut connoisseur – which feels very on brand for someone who keeps things running smoothly.
Role: Account Manager
Born and bred in Lower Hutt and a former HVHS local, Flinn has done the classic OE lap — before making his way back home last year.
While in the UK, he worked with the tech team at Harrods, helping streamline premium Apple product experiences for some very high-end customers. Basically, if someone wanted the best tech money could buy without the headache, Flinn was your guy.
These days, he brings that same calm, solutions-focused approach to helping clients find the right billboard fit without all the fuss.
Outside of work, Flinn is into football, league (Up the Wahs) and true crime docos. He’s also a self-proclaimed vexillologist (flag expert, for the uninitiated) and backs himself to go 100% on just about any world geography quiz put in front of him — a niche talent, but a strong one!
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