Meet Jake Cleland - Security Consultant at The Missing Link
At The Missing Link, our people are at the heart of everything we do. Their expertise and dedication drive IT transformation for our clients, delivering real impact every day. But there’s more to them than just their roles! In this series, we take a closer look at the unique passions, experiences, and quirks that make our team who they are, both inside and outside of work.
Jake’s journey to cyber security doesn’t follow the traditional playbook, unless that playbook includes music journalism, hex editors, and a deep mistrust of smart speakers. Equal parts sharp, subversive, and self-deprecating, Jake brings a writer’s eye, a hacker’s mindset, and a deeply human curiosity to everything he does.
From writing for millions to testing systems at The Missing Link, Jake’s story is as unconventional as it is entertaining. Let’s take five minutes to get to know him.
Tell us about yourself. Where did you grow up and what were your hobbies as a kid?
I grew up on the hard-boiled streets of the Mornington Peninsula, right at the point where farmland met the beach. From the dappled beauty of pinto mares braying in their paddocks to the turquoise surf lapping at golden sands, this splendour of nature drove me to my chief interest as a child: staying indoors on the computer.
It was all over the minute my dad showed me Windows 3.11 on the family PC. The tactile clunk of the power button, the crackle of static on the CRT monitor, the mechanical drives spinning up, every bit beeping and chattering as if the bones of the thing rattled itself awake. I spent hours trying to figure out how to play Hearts or tapping out short stories where my friends were wizards or seeing what I could break with a hex editor. After a few years of this I got to try going on the internet. I think that was my first mistake.
After those early days writing stories and exploring the family computer, what did you imagine yourself doing when you grew up? What was your first experience of working life like?
First it was a palaeontologist and then archaeologist, until a real-life one came to our school and said they'd found most of the stuff already and there weren't really any jobs left. By that point I'd graduated to a laptop and spent a lot of time failing to learn how to break computers in shady IRC channels, but back then "hacker" was mostly a type of guy you get for your heist rather than a job.
My dreams shifted towards the financial security of becoming a writer. In the meantime, I started packing shelves at the Target in Frankston. Horrible red undertones from the uniforms but nice enough people.
What did your path into writing look like?
Inspired by a tea towel I once saw that said "Don't let your dreams be dreams," I became a writer after all. I fell into writing music reviews thanks to a Twitter friend and managed to parley being rude and funny with excellent taste into writing for every publication I ever wanted. I even started one of my own (it went okay).
Within five years, I went from freelancer to intern to deputy editor, and eventually editor-in-chief of a publication read by a million people a month. Unfortunately, it was sold off to Bindi Irwin's publicist who wanted to turn it into the Daily Mail and, despite being a wisened 25 years old, I couldn't stop it ending in catastrophe. A few years later I'd finished ticking off the rest of the music journalist bucket list so I went back to university to pick up where I left off with the machine gods. After a few years doing tech support for a post-production studio, I did my OSCP and landed with The Missing Link a couple weeks later.
So where did that journey lead you - what’s your role at The Missing Link and what do you love most about it?
If there’s one throughline across everything I’ve done, it’s that I’ve always admired the people I work with. Here at The Missing Link, that rings especially true. My fellow security consultants are wickedly talented; some are downright scary in a ‘thank God they're on our side’ type of way. I’m constantly taking notes, learning from them as they go about being the best at what they do.
That respect extends to our clients as well. As much as we love showing off our technical chops, ultimately, we're trying to deliver clear risk assessments and actionable mitigation strategies. At this point, I don't know a single person who hasn't had their personal information leaked, but getting to work with clients who are so switched on and serious about protecting their users is one of the best parts of the job.
Looking back so far, are there any personal or professional achievements you’re particularly proud of?
A few highlights stand out. Becoming editor of the publication I loved most in the world and being able to pay writers I’d admired for years was a dream come true. I also had the chance to speak at conferences across the country about why music journalism matters, and I interviewed some of the best bands on the planet. I even got to ask Iggy Pop a personal question (off the record, of course).
On the tech side, a proud moment was helping solve the technical challenges of a visual effects pipeline just as a deadly pandemic hit and everything shifted to remote. It was chaos, but now I can say I played a tiny part in bringing to life the cinematic masterpiece that is Sonic the Hedgehog 2.
More recently, passing the OSCP exam and joining The Missing Link was a huge milestone. I now get to work with some of the sharpest minds in the business and feel like the dumbest person in the room every day. It’s great.
What inspires you, and where do you see yourself in a few years?
Currently I'm gathering support via various backchannels to make a move on our CISO, Aaron Bailey's job, but until that pans out, who knows? There are so many avenues.
One of the nice things about working here is there's a lot of support for taking initiative and I'm hugely motivated by people like Stefano Lanaro, Michael Newton, Sam Marshall, and Matthew Dobinson who build and maintain critical parts of the pen testing team infrastructure.
Supporting each other's work is really important to me and finding material ways to do that is always on my mind. Lately I've performed a number of highly successful social engineering engagements, so I'm currently focused on understanding those techniques better so we can deliver more realistic attack simulations for our clients.
Do you consider yourself a tech-freak and do you have a favourite gadget?
I consider myself an enemy of computers. That's why I spend so much time trying to break them! If I could do this job from a log cabin in the bush with nothing but oil lamps and a ton of books, I would. Unfortunately, the Lebanese bakery near my house is too good to leave.
While we continue to leverage rapid advances in technology, we have a responsibility to secure that technology, so I'll stick around in the big smoke trying to make things safer for people. But if someone tries bringing a smart speaker into my house, it's kill on sight.
If money wasn’t an issue, what would your dream day look like?
I wake up to the muffled chop of rotor blades. I'm on a helicopter. Sam Marshall is there with two snowboards. We rip out of the heli like demons at the crossroads and the wax hits the pow like it owes us money. I'm doing the sickest tricks all the way down the run. But the run ends with a massive cliff. It's okay, we brought parachutes.
We land at the Tomorrowland Winter stage. Avicii is there. He brings me up on stage. "Jake, I just want to thank you for spending your unlimited money to resurrect me. You are my true brother." But I have to go.
Naomi Klein wants me to read a draft of her new book. I'm getting hungry so I text her and ask if we can do it over a croissant. She loves that idea. We meet in Paris and I make a few edits. But I have to go.
Musee d'Orsay is unveiling their new attraction, a gigantic bust to honour history's greatest patron of the arts. They pull off the tarp. The sculptors have done a wonderful job capturing my likeness. My phone buzzes. It's those nerds at Davos. Apparently donating 400 trillion dollars to every gallery in the world has upset the global economy. But I have to go.
Every side of the political compass is championing me a hero because my actions were just vague enough to fit into their ideology. A new age of unity is proclaimed. It starts to rain. John Jurkov pulls up in a limo outside. "Jake, get in. This peer review needs to be done by five and only you can tell me whether the participle works in this sentence." But I have to go.
It's my birthday and all my best friends rented a house by the beach. We drink four glasses of wine and then people start going to bed.
"Do you have to go?" one of them asks.
But I don't.
Back in the real world, what are your weekends like? And what are your hobbies?
Typically it's either pubs, clubs, or ticket stubs. All of my friends have an abiding love of music whether it's at the bar or at the rave, but sometimes you just need to sit in a dark cinema somewhere.
When there's gaps in the calendar though, I'm probably working on certs, pulling apart code, or otherwise trying to learn new things.
I'm lucky in that I've made careers out of hobbies twice now and it's only deepened my passion for them. But when I'm not trying to write exploits or poring over documentation, I'm swinging between books both fiction (fantasy/sci-fi) and non-fiction (arts criticism, economic theory) or trying to touch grass at the lake near my house.
What would you say is the best thing about living in your city?
The passion and respect everyone has for each other's freedom. There is so much history where I live, and I don't mean "Australian" history as much as the history people brought here from all over the world. I step out my door and walk alongside families from some of the most beautiful parts of Earth like Lebanon, Greece, Nepal, Thailand, Palestine, Italy, Vietnam, and that shared humanity is something the people of Melbourne all deeply respect, and we're very outspoken about protecting it. We'll even accept people from Geelong, which just speaks to how much we value diversity. Yeah, it's a good town for it.
