Show Notes
Kyle Elliott, the Founder and Career Coach behind CaffeinatedKyle.com, joins the pod on his quest to transform boring job searches into something fabulous. Kyle specializes in helping job seekers, especially those in technology and cybersecurity, find jobs they love and express the value they bring to potential employers. Need to know the secret to acing your next tech job interview? Look no further than Caffeinated Kyle.
Timecoded Guide:
[00:00] Finding your own definition of fabulous
[06:06] Standing out in a tech job interview
[12:19] Dealing with and learning from job rejection
[16:41] Targeting your dream tech job & telling your career story
[21:33] Breaking into technology the easy way and the hard way
Sponsor Links:
Thank you to our sponsors Axonius and Uptycs for bringing this episode to life!
The Axonius solution correlates asset data from existing solutions to provide an always up-to-date inventory, uncover gaps, and automate action — giving IT and security teams the confidence to control complexity. Learn more at axonius.com/hackervalleyWith Uptycs, modern defenders can prioritize, investigate and respond to threats across the entire attack surface—all from a common solution: uptycs.com.
From your perspective, what makes someone fabulous?
Being “fabulous” can sound grandiose to most tech practitioners, but Kyle believes that everyone has the potential to be fabulous, especially when they’re forging their career path. There’s a lot of competition amongst large tech companies to find the employees that close skill gaps and stand out from the massive group of hungry job seekers. To be fabulous, one has to know how to stand out and what sets them apart.
“When I think of fabulousness, I think: What sets you apart from other people? I work with job seekers, so I think: What sets you apart from other job seekers or other applicants?”
When you look at standing out in a job interview, what are some of the key components that go into that?
Many job seekers that Kyle works with have the skills, meet the position requirements, show up for the interview, and still struggle with getting a job in tech. While this can happen for a variety of reasons, Kyle explains that a simple mistake job hunters are making is regurgitating their resume without backing up their experience. A strong story about the experiences you had and the value you delivered makes you memorable and explains what you can provide.
“When you're doing this, you want to think in the mind of a hiring manager. How have you added value to the organization? What sets you apart? I didn't just code, I didn't just have cross functional collaboration, here's the value to the organization and what sets me apart.”
How do you coach someone through being able to tell their story in an interview?
Career storytelling skills separate a potential employee from a pack of qualified applicants. However, a lot of technical people aren’t known for their storytelling skills or knack for creativity. Instead, Kyle recommends his clients in tech and cyber practice their storytelling through a more familiar world of spreadsheets. Each spreadsheet helps job seekers break down the value they bring with their skills, so they can tell a story that connects their past experiences to their future position.
“A lot of the people I work with in tech, they're amazing at their job, but they're just not used to practicing storytelling…It feels awkward. It feels different. It feels weird, because that's not something they’re used to.”
From your experience, what have been the easiest and hardest fields in technology to break into?
In Kyle’s opinion, there isn’t one field of the tech industry that’s easier or harder to break into. Instead, breaking into the tech industry relies more on professional experiences, background, and skillset. If the leap to tech feels like too many transitions at once, Kyle recommends slowing down to one transition at a time and building each experience off of one another. Instead of hiding that this may be a new path for you, embrace your past when job searching and explain why a potential employer should hire someone transitioning into the tech world.
“Everyone's like, ‘Kyle, how do I get a job in tech?’ I would start with your background, and I think that's gonna determine what's easiest or hardest for the person. What I always recommend is, try to make the least amount of transitions possible.”
---------------
Links:
Keep up with Kyle Elliott on LinkedIn and the Caffeinated Kyle website
Connect with Ron Eddings on LinkedIn and Twitter
Connect with Chris Cochran on LinkedIn and Twitter
Purchase a HVS t-shirt at our shop
Continue the conversation by joining our Discord
Check out Hacker Valley Media and Hacker Valley Studio
Recent Episodes
The AI Gold Rush in Cybersecurity with Chris Cochran
The new cybersecurity pioneers aren’t chasing alerts, they’re building with AI. But what happens when tools meant to assist begin making decisions for us? And what skills do we lose when ...
The AI That Tried to Escape with Ron Eddings
What happens when AI refuses to be replaced? This episode kicks off with a chilling real-world example of an AI threatening blackmail—and only gets more intense from there. Host Ron Eddings ...
Zero Trust Isn’t a Tool — It’s Everything with George Finney
What if Zero Trust isn’t a framework, but the only viable cybersecurity strategy—more about people than products? In this episode, George Finney, CISO at the University of Texas System and ...
Your Two-Year Edge Starts Now with Marco Figueroa
You won’t be replaced by AI—you’ll be replaced by someone using it better. Returning guest Marco Figueroa is back with a frontline report on the AI agent boom. This isn’t a prediction—it’s a ...
Badge Cloning, Alarm Triggers & Getting Hired to Hack with Greg ...
Most people think red teaming is digital—until someone bypasses your locks, plants a Raspberry Pi in your server room, and walks out with your data. That’s not sci-fi. That’s White Knight Labs. ...
Building Cyber Resilience Through Culture with David Shipley
What if fixing cybersecurity wasn’t about more tools, but about unlocking human potential? In this episode, Ron Eddings welcomes back David Shipley, CEO and Field CSO of Beauceron Security, for ...
Ditch the Spreadsheets: Smarter Crypto Security with Michael ...
Still tracking certificates in a spreadsheet? You’re not alone—and there’s a better way. In this special episode from RSA 2025, Ron sits down with Michael Klieman, Global Vice President of ...
Protecting People, Not Just Perimeters with Andrey Suzdaltsev
AI is reshaping the cybersecurity battlefield, and cyber adversaries are getting smarter. In this episode, Ron Eddings welcomes Andrey Suzdaltsev, Co-Founder and CEO of Brightside AI, for a look ...
Digital Clutter and the Death of Passwords with Collin Sweeney & ...
Passwords are the original digital clutter—messy, overstuffed, and way too easy to forget. Like a junk drawer full of old keys and cables, we keep tossing more into them, hoping they’ll somehow ...
What Most Cybersecurity Advice Misses—And How to Fix It with ...
What if the biggest threat to cybersecurity isn’t attackers—but the defenders themselves? Why are we still building tools for experts in a world where technical skills are fading fast? In this ...
WORK WITH US
PODCASTS + SPEAKING + EVENTS
Are you the best kept secret in cybersecurity? Let's change that by partnering together for podcast ads, social campaigns, and your next event or keynote. Send us your details to get started.
Thank you!
We will be in touch soon and reach out to you at