Dive into the creative world behind OTTOBOX: Patch or Perish, Automox’s first-ever video game. In this episode of Automox Insiders, host Maddie Regis chats with Senior Brand Manager Jonah Phillips about transforming patch management into an interactive gaming experience. From retro music production to villain design inspired by real IT challenges, discover how Automox blends creativity, technology, and cybersecurity culture into one epic adventure.
In this episode of the Autonomous IT, host Landon Miles dives deep into the world of vulnerabilities, exploits, and the psychology behind cyberattacks. From the story of Log4j and its massive global impact to the difference between hackers and attackers, this episode explores how and why breaches happen—and what can be done to stop them.
Joining Landon is Jason Kikta, Chief Technology Officer and Chief Information Security Officer at Automox, Marine Corps veteran, and former leader at U.S. Cyber Command. Together, they break down attacker motivations, how to recognize threat patterns, and why understanding your own network better than your adversaries is the key to effective defense.
Key Takeaways:
Whether you're a cybersecurity professional, IT leader, or just curious about how cyberattacks really work, this episode offers practical insights from the front lines of digital defense.
In this episode of the Hands-On IT podcast, Landon Miles interviews Anthony Maxwell, who is a software engineer at Automox. They discuss Anthony's journey from IT operations to software engineering, and his home lab setup. He discusses his favorite projects, the skills he's learned, and how he applies them in his professional life. Anthony also provides insights into using Automox for policy compliance, offers advice for those looking to start their own home labs, and shares his thoughts on virtualization, operating systems, and staying updated with technology trends.
This episode originally aired on July 25, 2024.
In this episode, host Jason Kikta talks with Dmitri Alperovitch – CrowdStrike co-founder and chairman of the Automox board – about how speed and precision define modern cyber defense. Alperovitch explores how the OODA loop (Observe–Orient–Decide–Act), a concept rooted in military strategy, can help IT and security teams detect, respond, and adapt to threats in real time.
They discuss why cloud-native automation is essential for staying ahead, how to close gaps between IT and security teams, and what happens when organizations react too slowly. Drawing on decades of experience in cybersecurity and threat intelligence, this conversation challenges you to rethink what it means to be fast enough to defend your environment.
This episode originally aired on June 13, 2024.
In this episode of Product Talk, host Peter Pflaster sits down with Automox Staff Security Engineer Henry Smith to discuss what it really means to be secure by default. Together, they explore how Automox builds security into the foundation of its products, from engineering practices to company culture.
You’ll learn how Automox’s “no security tax” philosophy gives every customer access to enterprise-grade protection — without hidden costs or trade-offs. Henry also shares his journey from IT support to cybersecurity engineering, offering practical advice for anyone looking to grow a career in IT or security.
Tune in to hear how Automox approaches product security, fosters trust between engineering and security teams, and collaborates with industry peers to keep customers safe.
CFOs Ziad Fanous (Automox) and David Mehok (formerly CFO of Q2) join host Evan Kiely to break down how IT transformation drives real business value—not just cost savings. They share candid lessons from decades in finance leadership on:
A must-listen for IT and security leaders who want to secure budget, prove ROI, and build stronger relationships with finance.
This episode originally aired February 20, 2025
Happy Patch Tuesday! In this October episode, security specialists Ryan Braunstein and Mat Lee break down some of the month’s most critical vulnerabilities — and why this batch of CVEs might just be the spookiest yet.
The duo dives deep into:
With expert insights, real-world context, and a touch of humor, Ryan and Mat unpack what these vulnerabilities mean for IT and security pros — and what steps you should take right now to stay protected
🎃 Tune in for a fast, insightful rundown of October’s top Patch Tuesday updates.
Jeremy Maldonado breaks down cybersecurity fundamentals from a real-world IT operations perspective. From phishing and social engineering to patching best practices and zero trust, Jeremy shares practical insights to help you protect your organization — starting with your own behavior.
He covers:
Whether you’re new to cybersecurity or want to tighten your patching strategy, this episode gives you a tactical refresh on where to focus your attention.
What is a CVE – and why does it matter to your patching process? Landon Miles breaks down CVEs, CVSS scores, and CNAs – covering how they work together, what to prioritize, and how to respond. Learn how to assess risk, spot active exploits, and streamline remediation with clear, actionable steps.
In this episode, Automox CISO Jason Kikta strips away the noise and focuses on the three core pillars of secure IT operations: asset inventory, patch management, and identity and access management (IAM).
Jason shares firsthand stories from U.S. Cyber Command and explains why getting the basics right isn’t optional — it’s essential. Whether you’re building a modern security program or tightening existing controls, this episode delivers clear guidance on where to focus and why.
🎧 Topics covered:
Perfect for IT and security leaders looking to sharpen their foundational strategies.
In this episode of the Automox CISO IT Podcast, host Jason Kikta, CISO at Automox, explores how CISOs can advocate for automation maturity across IT and security teams. Jason breaks down why automation is critical for:
From worms of the early internet to today’s rapid weaponization of exploits like Log4j, Jason shares lessons from the field and why automation is no longer optional for security leaders. Whether you’re focused on patching, configuration, or incident response, this episode shows how automation maturity improves resilience, efficiency, and your ability to outpace attackers.
This episode originally aired February 16, 2024
In this episode of Product Talk, host Peter Pflaster sits down with JoLynn Dixon, Senior Director of Product Management at Automox, to discuss the future of autonomous endpoint management (AEM) and how Automox is shaping the path forward.
JoLynn shares her background in product leadership, the vision behind AEM, and why prioritizing customer feedback is central to Automox’s roadmap. You’ll also hear how Automox is:
If you’re an IT professional looking to cut risk, save time, and modernize endpoint management, this episode gives you a front-row seat to how Automox is leading the charge.
In this episode of Automox Insiders, host Maddie Regis chats with IT Help Desk Technician Emilia Keeney about her path into IT, her experience joining Automox, and why automation is the unsung hero of IT. Emilia shares her journey through an accelerated IT program, what it’s like working on a small but mighty IT team, and why even the simplest support tickets can be rewarding. The episode wraps up with a fun word association game you won’t want to miss.
This episode originally aired February 18, 2024.
In this episode of Executive IT, host Evan Kiely sits down with Alan Taylor, COO of Maxio, to explore how IT and security shape business reliability, compliance, and growth. Alan shares his perspective as a seasoned operator in private-equity backed SaaS companies, covering:
Whether you’re a technology leader, operator, or business executive, this conversation offers actionable insights on making IT and security a business driver — not an afterthought.
In this episode of Automox Insiders, host Maddie Regis sits down with Katie Bleichman, Director of CX Operations and Enablement at Automox. Katie shares her inspiring journey from two decades in elementary education to leading customer experience in the SaaS and cybersecurity world. Discover how skills from the classroom translate into IT, what it takes to adapt and grow in a new career path, and why lifelong learning is key to success. Whether you’re considering a career shift or want to hear how customer education empowers users through Automox University, Katie’s story is filled with practical insights and motivation.
In this episode, Jason Kikta discusses the critical relationship between IT and security, emphasizing that great security begins with a solid IT foundation. He explores the importance of establishing a baseline for normalcy, the role of user safety in preventing security breaches, and the need to understand insider threats. Jason concludes with discussing the 'big three' of cybersecurity, which are:
This episode originally aired October 10, 2024
Stay ahead of September 2025 Patch Tuesday. Automox experts Ryan Braunstein, Henry Smith, and Seth Hoyt break down three high-impact items you need to act on now: Hyper-V privilege escalation, XAML/Phone Link elevation paths, and an NTFS remote code execution.
You’ll get:
Subscribe, share with your team, and tighten your local attack surface today.
In the second half of this crossover between Hands On IT and Automate IT, hosts Landon Miles and Jeremy Maldonado shift from defining IT problems to actually building, testing, and refining solutions. They dig into choosing the right tools without getting lost in endless options, the value of learning from APIs and documentation, and why “don’t reinvent the wheel” is a mantra every IT pro should adopt.
Along the way, they share real-world stories about discovering hidden libraries, avoiding common pitfalls, and leaning on version control to save projects from chaos. From Python and Bash basics to Git, Postman, and even the “bus test” for documentation, this episode is packed with practical lessons to help you turn automations into lasting, maintainable solutions.
Whether you’re just starting your automation journey or looking to optimize and scale what you’ve already built, you’ll find insights, strategies, and inspiration to take your IT problem-solving further.
Awesome-Selfhosted GitHub Link: https://github.com/awesome-selfhosted/awesome-selfhosted
In this special crossover between Hands On IT and Automate IT, hosts Landon Miles and Jeremy Maldonado dive into the building blocks of IT solutions. They share practical ways to approach automation without the overwhelm—starting from defining real-world problems and breaking them into manageable steps. Along the way, they explore Linux as a problem-solving tool, home lab tinkering, Docker, Proxmox, and the power of learning by experimenting (and breaking things!). Whether you’re new to IT or ready to sharpen your automation mindset, this episode is packed with insights, inspiration, and actionable takeaways.
Stay tuned for Part 2, where we dig into the tools, testing, and turning automations into solutions!
Awesome-Selfhosted GitHub Link: https://github.com/awesome-selfhosted/awesome-selfhosted
It’s not just a show, it's a lifeline for how to unscary a seemingly daunting career journey – no matter where you're at in your IT or security hustle.
From super-talented IT cartoonist and influencer marketing service agency co-owner, Forrest Brazeal, and gifted Automox VP of Customer Experience, Charles Coaxum, to the sagely verbose CISO and VP of Product at Automox, Jason Kikta, and Gong’s inspirational Director of IT, James Sennett – our handpicked line-up of industry trailblazers won’t just talk about how to advance. Instead, they’ll walk you through real-life strategies to help you climb the career ladder and stay on the top rung once you get there.
This show was broadcast live Wednesday, October 30, 2024 at 12 PM Central Time.