Welcome to the Opkalla IT Matters Podcast, where we discuss the important matters within IT as well as the importance of IT across different industries and responsibilities.
About Opkalla:
Opkalla helps their clients navigate the confusion in the technology marketplace and choose the technology solutions that are right for their business. They work alongside IT teams to design, procure, implement and support the most complex IT solutions without an agenda or technology bias. Opkalla was founded around the belief that IT professionals deserve better, and is guided by their core values: trust, transparency and speed. For more information, visit https://opkalla.com/ (https://opkalla.com/) or follow them on LinkedIn (https://www.linkedin.com/company/opkalla/).
Why Curiosity Still Matters in IT Leadership, with Neil Stein
This episode of the IT Matters Podcast features a conversation between host Keith Hawkey and guest Neil Stein, seasoned IT leader and Senior Vice President of Technology Services at OrthoCarolina. Neil shares insights on the evolution of technology, problem-solving skills, and the importance of curiosity in IT. Together, they explore how a solid foundation of knowledge, paired with the habit of asking the right questions, can shape the next generation of tech leaders.
Conversation Highlights:
0:00 Introducing Neil Stein and his IT journey
[5:39] From chemistry to a career in technology
[12:43] GUIs and the art of troubleshooting
[16:28] Advice for new IT professionals
[20:44] Why the best leaders keep asking questions
[29:04] Connect with Neil
Notable Quotes:
"Talk to your peers. Question things. Be curious. Those are the fundamental pieces as you're a leader." - Neil Stein [18:20]
"From day one, as soon as you graduate high school, be the person asking the questions and never stop." - Neil Stein [21:28]
Connect with Neil Stein on LinkedIn (https://www.linkedin.com/in/steinne/).
Read the transcript: Episode 42 (https://cdn.prod.website-files.com/65fda2f9fddf07cb8e178480/6ac954ebb2a861a324af17be_IT%20Matters%20Podcast%20-%20Episode%2042_transcript%20(2).pdf)
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.
9 Jul 2026
IT Leadership in a Fast‑Changing World, with Derek Jones
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 (https://www.linkedin.com/in/derek-jones56/).
Read the transcript: Episode 41 (https://cdn.prod.website-files.com/65fda2f9fddf07cb8e178480/6a50030b88c6375f59d819e2_ep41.pdf)
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.
17 Jun 2026
Debunking Cybersecurity Misconceptions, with Michael Irwin
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 (https://www.linkedin.com/in/michaeljamesirwin/).
Read the transcript: Episode 40 (https://cdn.prod.website-files.com/65fda2f9fddf07cb8e178480/6a31a7701463757678718096_IT%20Matters%20Episode%2040_otter_ai_transcript.pdf)
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.
Who has been a guest on IT Matters [Opkalla]
Names identified in recent episode analyses. Showing up to five guests.
Nathanael Dick
Troy Penny
Shane Creech
Stephen Self
Jeff Garrett
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
7,536
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
2 ratings
Spotify
5.0 / 5
2 ratings
Podcast Authority Score: 54 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
57
Social presence
0
YouTube
68
Engagement
60
Contact IT Matters [Opkalla]
Guest appearances
Does not typically book guests
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Questions about IT Matters [Opkalla]
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IT Matters Podcast host the show. Published by Opkalla.
How often do new episodes come out?
The show publishes monthly, based on its RSS feed.
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