IT Matters | Tech Solutions and Strategies for Every Industry

This episode of the IT Matters Podcast features a conversation between host Aaron Bock and guest Derek Jones, a longtime technology executive with experience leading IT teams for organizations of more than 350 people. Derek shares lessons from his career, shaped by his “offensive lineman mindset,” a philosophy rooted in team-first leadership. The discussion explores how IT leaders can stay relevant amid rapid technology change, especially the accelerating pressure around AI adoption.
Conversation Highlights:
0:00 Introducing Derek Jones 
[3:10] From Operations to IT Leadership 
[11:03] Leading Enterprise Transformations 
[18:46] Developing Service-Oriented IT Teams 
[40:57] Decisions IT Leaders May Regret
Notable Quotes:
"Especially in this remote world now, where we've got technology leaders everywhere, it's really hard. There's still a value of a handshake, there's still a value of walking that mile in another person's shoes." - Derek Jones [16:26]
"Invest in yourself, invest in your team, and be a team player, and you're gonna win half the battle there." - Derek Jones [45:38]

Connect with Derek Jones on LinkedIn.
Read the transcript: Episode 41

The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.

On this episode of the IT Matters Podcast, our host is joined by Michael Irwin, CISO for Odyssey Logistics, to discuss the challenges and misconceptions in the cybersecurity industry. Together, the emphasize the importance of understanding one's environment, prioritizing proactive measures over reactive chaos, and addressing legacy infrastructure.
Conversation Highlights:
0:00 Michael Irwin, CISO for Odyssey Logistics
[6:05] Michael's Cybersecurity Journey
[8:54] Challenges in Cybersecurity Investment
[15:22] Proactive Disruption vs. Reactive Chaos
[31:47] Advice for Emerging Cybersecurity Leaders
Notable Quotes:
"Cybersecurity is asymmetrical in general. We have to protect everything, and a bad actor has to find the one thing that we didn't protect." - Michael Irwin [9:10]
"Focusing on positive culture and work-life balance and really supporting the people on your team moves the needle more than anything else." - Michael Irwin [33:40]

Connect with Michael Irwin on LinkedIn.
Read the transcript: Episode 40

The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.

On this episode of the IT Matters Podcast, our host is joined by Nathanael Dick, Vice President of Cybersecurity at SteelFab, for a deep dive into the evolving world of cybersecurity compliance. Together, they explore why frameworks like the Cybersecurity Maturity Model Certification (CMMC) are becoming essential for modern organizations and how compliance can strengthen overall security. Nathanael also shares why companies should shift their mindset and view compliance not as a burden, but as an opportunity for business improvement.
Conversation Highlights:
0:00 Introducing Nathanael Dick, VP of Cybersecurity at SteelFab
[2:23] Two Truths and a Lie - Cybersecurity Edition
[4:50] Nathanael's Background & Experience
[8:54] Compliance as a Growth Opportunity
[26:38] A Message to the Industry
Notable Quotes:
"What is always so critical to stop the bad guys is to be aware." - Nathanael Dick [28:17]
"Stay cyber safe. Stop and think." - Keith Hawkey [29:19]

Connect with Nathanael Dick on LinkedIn.
Read the transcript: Episode 39

The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.

On this episode of the IT Matters Podcast, our host is joined by Troy Penny, Global Vice President of Information Technology at Harsco Rail. As a children’s book author, Troy has learned a lot about the power of storytelling in technology. Together, him and our host discuss the influence of leadership and culture in IT, aligning business with technology, and the importance of stories in a quickly-changing technology landscape. 

Conversation Highlights:
0:00 Introducing Troy Penny, Global VP of IT at Harsco Rail
[12:08] Learning Leadership in IT
[17:15] Growing from IT Challenges and Failures
[22:01] Connecting Strategy, People, and Technology 
[29:42] Finding Your North Star

Notable quotes:
“Great technology leaders don't just think in system frameworks, they think in stories.” - Keith Hawkey [01:13]
“You have to look at IT through the eyes of the business.” - Troy Penny [16:34]

Connect with Troy Penny:
https://www.linkedin.com/in/troyspenny/

Read Troy’s books:
https://www.amazon.com/stores/Troy-Sheridan-Penny/author/B0F7LSBM8Y/allbooks?ccs_id=b434535d-3802-4e17-8639-015db6324679
Read the transcript: Episode 38

The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.

On this episode of the IT Matters Podcast, our hosts are joined by Shane Creech, Vice President of IT at Ob Hospital Group. Together, they unpack what it means to lead IT when the stakes are high, and the lights absolutely must stay on. Listen to hear Shane share -  
 
How his path from aspiring medical lab technician to healthcare IT executive shaped the way he thinks about systems, people, and risk 
What separates IT leaders who survive risk from those who don’t 
Advice for anyone in IT feeling pressure to handle regulations, system downtime, the growing role of cloud and AI, and more 
 
Conversation Highlights: 
0:00 Introducing Shane Creech, VP of IT at Ob Hospital Group 
[5:55] Shane’s Journey in IT 
[10:39] Navigating the Challenges of IT in Healthcare 
[15:25] The Growth of Cloud Tech in IT 
[25:32] The Future of AI 
 
Notable quotes: 
“It’s more than a bad day today. It’s a bad day for the next five years.” - Shane Creech [14:47] 
“It comes down to the metrics that matter.” - Shane Creech [27:00] 
 
Connect with Shane Creech: 
https://www.linkedin.com/in/shane-creech/ 
 
Read the transcript: Episode 37 
 
The IT Matters Podcast is about IT matters and matters pertaining to IT. It is produced by Opkalla, a technology advisory firm that helps their clients navigate the confusion in the technology marketplace and choose the solution that is right for their business.