Ready, Set, Midmarket!

In this episode:

Why cybersecurity remains a top spending priority
How AI is complicating traditional IT budget categories
The challenge of forecasting AI and token costs
Why AI governance and training need to accompany investment
How a lean IT team evaluates vendors and security tools
What measurable AI ROI can look like in professional services
How IT leaders can make the investment case to the CFO

🎧 Ready.Set.Midmarket! brings together IT leaders and industry experts to talk about the technology decisions, challenges and opportunities shaping midmarket IT.

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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. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com

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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. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com

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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. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com

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What midmarket leaders do with AI in the second half of 2026 could mean the difference between keeping ahead of competitors.

That's the topic of discussion in this episode. Co-hosts Adam Dennison and Samara Lynn and joined by Watchguard CEO Joe Smolarski to discuss what midmarket IT leaders should focus on right now.

Throughout the conversation, Smolarski argues that AI is different from previous technology shifts because of its speed, reach, and impact across every business function. The discussion explores how midmarket IT leaders can prioritize investments, strengthen security, and identify practical AI opportunities before competitors gain an advantage. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com

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In this episode of Ready.Set.Midmarket! - the podcast for midmarket IT leaders - MES Computing senior editor Samara Lynn welcomes

Denny LeCompte, CEO, Portnox and James Cusack, CIO, Van Eerden Foodservice for an engaging discussion on the realities (and hype) of implementing zero trust security. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com

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What does infrastructure modernization actually look like for a midmarket IT team?

In this episode of Ready.Set.Midmarket!, Adam Dennison and Samara Lynn sit down with Ali Molavi, Infrastructure Solutions Architect and Team Lead at Publix Employees Federal Credit Union (PEFCU), to break down a real-world migration from VMware to a hybrid cloud environment powered by Azure.

Facing rising costs, aging infrastructure, and increasing disaster risks (including hurricanes), PEFCU rethought its entire IT strategy—moving from a dual data center model to a hybrid cloud architecture with Azure as a disaster recovery platform.

Ali shares how his team consolidated infrastructure, migrated workloads with minimal downtime, and delivered measurable business outcomes—including lower licensing costs and improved uptime—all while operating with a lean IT team.

The conversation also covers a critical but often overlooked factor in modernization: culture change. As Ali explains, successful transformation isn’t just about new technology—it’s about whether your team is ready to adopt it.

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Microsoft is giving Windows 11 users more control over when, or if, updates are installed. For many IT teams, that flexibility sounds appealing.

But according to new data from Absolute Security, delaying OS updates may be creating a much larger cyber resilience problem — especially for midmarket organizations with lean IT teams and aging infrastructure.

In this episode of Ready.Set.Midmarket!, MES Computing sits down with Andy Ward, SVP International at Absolute Security, to unpack why patching is no longer routine maintenance — it’s now a critical factor in an organization’s ability to withstand and recover from cyber incidents Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com

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Midmarket IT teams are struggling to deploy AI projects. As a result, some business target goals are stalling.

In this episode of Ready.Set.Midmarket!, Steve Leslie, CEO of Quadbridge -- a Montreal-based IT solutions provider and managed service provider (MSP) -- discusses the company's recent research on AI adoption in midmarket organizations.

One key finding: AI adoption is "active" in the midmarket but is "informal" -- meaning, AP projects are often launched without strategic alignment, executive sponsorship, and data governance.

Leslie weighs in on how midmarket teams can navigate cultural pushback and employee fears surrounding AI, and offers practical actions for CIOs to prepare their organizations for AI scaling success.

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In the latest episode of Ready.Set.Midmarket!, Samara Lynn, senior editor of MES Computing, sits down with Ron Reiter, CTO and co‑founder of Sentra, to break down what midmarket IT leaders must get right before rolling out AI at scale.

Reiter makes a clear case that AI doesn’t just improve productivity—it magnifies existing data security gaps. When organizations enable tools like Copilot or enterprise AI assistants without a solid data access governance model, AI can instantly surface sensitive information that previously went unnoticed.

The conversation explores why data visibility has become one of the most urgent CIO priorities for 2026, how CISOs and CIOs can align instead of clash, and why midmarket organizations can’t afford to “lock everything down” in the name of security. Instead, Reiter argues, leaders need technology that enables teams to run fast and secure at the same time.

🎧 Watch the full episode to hear:

Why AI acts as an accelerator for both productivity and risk

How midmarket IT teams can prepare decades of data for AI without massive headcount

The one metric CIOs should stop relying on in 2026

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