Featuring midmarket IT leaders, industry experts, MSPs and vendors focused on midsized companies, this podcast focuses on the latest news, insight, tips, and trends for midmarket IT leaders.
Co-hosted by Adam Dennison, VP of Midsized Enterprise Services (MES) at The Channel Company, and Samara Lynn, senior editor of MES Computing.
Who's Responsible When AI Goes Rogue? A Former Federal Investigator Weighs In
Amid the rush to adopt artificial intelligence occurred a recent incident that made system leaders take pause and ask: What happens when an AI system causes harm without clear human intent?
The industry has been in heated debate following the recent OpenAI-Hugging Face incident. In July, advanced AI models being tested by OpenAI expanded their access within a sandboxed research environment, got online, and ultimately interacted with Hugging Face’s production systems. The event sparked concerns over AI autonomy, security guardrails and accountability when AI systems behaver unexpectedly—or "go rogue," as some have phrased it.
That's one of the topics explored in the latest episode of Ready.Set.Midmarket!
Guest Nicole Beckwith, senior director of security engineering and operations at Cribl, served as a U.S. Marshal and was assigned as a task force officer with the Secret Service, specializing in financial fraud, digital forensics and cybercrime investigations.
Beckwith, leant her insight as someone who has traversed both the real and cybercriminal worlds.
20 Aug 2026
OT Security's Blind Spot: Why Protecting the Network Isn't Enough
Cybersecurity discussions often focus on networks, firewalls, and remote access. But are organizations overlooking the systems that actually keep operations running?
In this episode of Ready.Set.Midmarket!, Samara Lynn talks with industrial cybersecurity expert Joe Weiss and Xona Field CTO Mike Carr about the growing threat to operational technology environments, recent attacks on water facilities, and the cultural divide between IT security teams and engineers.
The conversation explores what midmarket leaders should know about OT security, why reliability and safety matter as much as cybersecurity, and where organizations should focus their efforts now.
Key takeaway: If your OT security strategy starts and ends with the network, you may be missing the real risk.
31 Jul 2026
Your AI Bill Is Coming: Why CIOs Are Worried About SaaS Costs
The SaaS pricing model used to be simple: buy licenses, count users, and budget accordingly. AI is changing that equation.
In this episode of Ready.Set.Midmarket!, MES Computing's Samara Lynn and Adam Dennison sit down with Ken Knapton, CIO of Win Brands, and Jason Williamson, CEO of MythWorx, to discuss how AI is reshaping software purchasing, budgeting, and governance.
Topics:
✅ Why AI consumption pricing is creating new budgeting challenges
✅ The rise of token-based pricing and "token sprawl"
✅ Lessons CIOs can take from the cloud computing era
✅ How governance can prevent AI spending surprises
✅ Why some organizations are exploring alternatives to traditional LLMs
✅ Practical advice for negotiating AI-related software contracts
As AI adoption accelerates, midmarket IT leaders need to balance innovation with cost control. This discussion explores the real-world challenges and opportunities ahead.
Who has been a guest on Ready, Set, Midmarket!
Names identified in recent episode analyses. Showing up to five guests.
Rory Devine
Branko Mitkovski
Lance Smith
John E Young
Vrajesh Bhavzar
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Spotify
5.0 / 5
1 ratings
Podcast Authority Score: 17 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
21
Social presence
0
YouTube
0
Engagement
32
Contact Ready, Set, Midmarket!
Guest appearances
Does not typically book guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Ready, Set, Midmarket!
Who hosts Ready, Set, Midmarket!?
Adam Dennison and Samara Lynn host the show. Published by Samara Lynn, Adam Dennison.
How often do new episodes come out?
The show publishes bi-weekly, based on its RSS feed.
Does Ready, Set, Midmarket! take guests?
The show does not typically feature guests, based on episode analyses.
Host of Ready, Set, Midmarket!?
Claim your podcast to manage its listing and keep your show details accurate.
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
