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A passion and desire to be able to market his band better ultimately began the journey of Wynne Digital being created!  Turns out that Caleb was better at promotion than he was at playing the bass.  From setting up shop in his UK bedroom three years ago to moving his digital marketing agency back into the streets of South Melbourne, Caleb looks back at his time as an account manager and director and refuses to follow suit with the typical agency way.  Wynne Digital refuse to lock their clients into contracts and actually set realistic expectations.  Better yet, who wouldn’t want a team working for them whose ultimate end goal is to become such an integral part of your business, that they land an invite to the Christmas Party!?

In your own words… What is Wynne Digital?

Wynne Digital is an ambitious, results-driven dedicated digital agency.  We put people and relationships first.  We understand that behind every business and client is a real person.

Tell us the story – your story – of how you came to be in the digital space and offering your services to clients around the world?

I studied marketing because I wanted to better “market” the band I played in when I was younger.  Turns out, I was much better at promotion than playing bass.  When it came to deciding what I would do with my degree, I turned to my best friend Kryan.  He’d been working in advertising as a creating for a few years and his career seemed amazing.  I asked him how I could get a job like his, he flipped the question back on me asking what I wanted to do.  I said I wanted to talk to clients and come up with the strategy and ideas.  He explained to me that I’d described his account manager, so I set out to become an account manager.

I landed a job as a Google Ad Specialist, then quickly moved on to being an account manager.  After a few more promotions and years in Australia, I decided I’d go and travel.  Whilst backpacking South East Asia, I had one client (my uncle), Kyran also started sending me some projects and suddenly, I had a taste for “freelancing”.

Arriving in London, my freelancer income wasn’t enough to support me, so I headed back into an agency as a “Business Director”.  The salary was amazing and I thought I’d made it!  But I hated the job, they were everything I couldn’t stand about agencies.  So I left and picked up a “client” which was three days a week in their office, which felt like a part-time job.  I (sometimes) used other days in a week to start building a site and trying to acquire more clients, it was February 2020.  Through world circumstances, I lost my three day a week job and my uncle as a client.  But, I was already one foot into starting my own ‘thing’, so I decided to forge ahead.

Three years on, I moved WD (Wynne Digital) back to Australia.  Set up an office in South Melbourne (I sit two desks down from Kyran), and hired the amazing Madeline, who’s been an enormous factor in WD’s growth in Australia.  We still have some clients back in the UK but we are mostly based in Australia now.

What was your “lightbulb moment” – the moment you realised that Wynne Digital would be your footprint on the world?

There’s been a few, getting my first invoice paid whilst backpacking and thinking, wow this is all mine and can go a long way in Thailand.  I didn’t entirely understand tax back then!

The next most significant would be a certain tipping point in the UK where I realised I could pay my own salary, then have some leftovers to start getting channel-specific freelancers to help me out, and started to realise I could continue to grow.

Everybody has something they love, what do you love about your ‘job’?

The conversations!  I honestly just love talking about digital marketing.  For big projects, we’ll get clients into our office and spend 2-3 hours brainstorming their entire marketing plan.  From the first interaction users have, right through to the bottom of the funnel “buy now” messaging.  Those days are my favourite.

What do you find is the main reason that keeps you getting up every morning, heading out the door and off to work?

The people, I love what I do but hanging out with Maddie and Kyran every day is awesome.  We’ve also aligned ourselves with clients and other businesses that we get along with.  So often work calls just feel like catching up with mates.

Tell us your secret… What are some of the little joys that you bring to your clients who have entrusted you to help them with their digital marketing?

From what I gather it’s that we’re on the clients team.  I’ve been on calls with Google and Meta late at night on behalf of our clients.  Maddie’s stayed up until midnight to put ads live for Black Friday sales.  I’ve built ad accounts on weekends when it’s been urgent.  We’ll happily go above and beyond because we genuinely want our clients to see success.  We don’t see it as a chore, the flip side is – if it’s going well, we might knock off early on a Friday.  Whenever we bring a client on board, we always tell them our ultimate goal is to be so integral to the team we get an invite to the Christmas Party.

If we were to spend a day in your shoes, what would that look like?

Usually, I’ll get out of bed around 8.15am, shower, slam down some breakfast and get into the office by 9:00am.  I start my day with the same two tasks: clear my inbox by adding any actionable items to my to-do list for the day, and reconcile accounts in Xero.

From there, I’ll start working through the to-do list and adding things from the weekly to-do that I can action that day.  Around 9:45am Maddie and I will head out for coffee and play some quick table tennis.  Depending on the day I’ll have personal training or hit the gym before lunch.  Unless it’s a Friday in which case Maddie and I will have our sacred ritual Friday Pub Lunch.  The rest of the day will be filled with chatting with clients, working on proposals, tweaking ad accounts and checking client’s performance.

What do you consider a good day at work for you?

Being Digital Marketing, we can work from anywhere so the good days have been; on the Greek Islands, Vietnam, and the outback and I’m currently working from Edinburgh by day and attending Fringe Festival gigs at night.  Or when Maddie brings her table tennis skills and we have an epic game.  But, as for a typical South Melbourne fulfilling day, it would be when we get to chat to clients and celebrate wins with them.  Winning new business always feels damn good too!

Tell us about what you do and what sets you apart from other businesses that offer digital marketing?

I’d say it’s the reason I started Wynne Digital.  The agencies I’ve worked for in Australia and the UK are all so focused on their own revenue growth.  The standout agency structure is salespeople who have monthly targets to hit in order to make their commission.  They’ll then embellish the agency’s capabilities and potential results.  Once the deal is done, it will be handed to an account manager who will have to pick up the pieces and retain that client.  Not WD, we won’t lock clients into contracts and we set realistic expectations, we ensure clients know the risk -vs- potential reward.  Our clients stay with us for a long time, and our revenue grows because we do a fantastic job for them.

Every business needs an adviser… who do you turn to for help at Canny Group and with so many accountants Geelong has on offer, why Canny Group?

Adam has been advising me since the beginning of 2023.  Canny Group seemed an obvious choice as they’ve been a client of Wynne Digital’s for some time.  But I love how much we align.  Getting to know the team, we’ve built up friendships.  I love that they’re damn good at their jobs, they’re professional but also have a unique personality and vice.  It’s what I’m hoping WD can be like one day.

What kind of support have you received from Canny Group since joining forces with them as your accountant?

It’s been incredible, for the two and a half years I’d been running WD, I’d been flying by the seat of my pants.  I’d hit some milestones, hired a full-time employee, rented an office space, and bought a car through the business.  I had a feeling things were going well but I couldn’t always be sure.  I’ve been weighing up our next hire but was nervous and figured I’d need someone else’s advice.

Adam’s helped me put together a budget, showing me when I’m making a profit and areas to improve.  It’s given me the perspective to be even more proud of Wynne Digital and given me the confidence to bring someone else on board.

Looking into your Wynne Digital crystal ball… what do you see the future looking like for you and your business?

It’s so hard because sitting in my London bedroom three years ago, I never thought I’d be here.  But we’ll be bringing someone else on board full-time before the end of the year.  The dream is to have an in-house specialist/senior in each of our services with their own junior that they’ll be mentoring.  Then I can just do what I love most and chat digital with clients.  But if the next few years can even be half as good as the first three, I’ll be happy!

How do we get in contact with you to have a chat about your services?

If it’s not already clear, I love talking about digital marketing and brainstorming ideas.  So, if you want to have a chat about what you’re currently doing/not doing or what I’d do if I were running your business, feel free to hit me up.



Phone: 0475 707 237

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