Ready, Set, Midmarket!

Commvault Field CTO Vidya Shankaran explains why AI agents, machine identities and increasingly complex data environments are forcing IT leaders to rethink what cyber recovery really means. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

AI is changing the cyber threat landscape, but attackers are still exploiting something much older: human trust. In this special crossover episode of Ready. Set. Midmarket! and Ctrl Alt Lead, Samara Lynn and Tom Allen sit down with Cynthia Kaiser, former FBI Deputy Assistant Director of Cyber and current head of Halcyon’s Ransomware Research Center, to examine what today’s cyber threats mean for I...

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...

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 on...

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 faciliti...

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 consum...

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...

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 for information about our colle...

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, a...

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!, M...

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 mid...

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 ente...

In this episode of Ready. Set. Midmarket! we explore the evolving landscape of cybersecurity leadership in 2026 with leading CISOs and industry innovators. Discover the key shifts, challenges, and strategic priorities shaping the future of security for midmarket organizations. Our Guests: Richard Bird - Chief Security Officer, Singulr AI Cyrus Robinson - Vice President of Security Operations at C3...

Shadow AI is already here. Get practical guardrails, AI council tips, and the training/certs to scale safely—plus why agentic AI changes midmarket security. Guests Raj Dubey, CTO, LT, and Jay Bavisi, President, EC Council lend their expertise and insight on the reasons why IT leaders must level up their AI skills. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for informatio...

Executive leadership wants AI and they want it now. Successful AI implementation is on IT executives' roadmaps in 2026 and that involves conveying realistic goals to executive leadership, engaging in risk assessment, agile project management, and preparing data for AI. Midmarket IT leaders Jason Frame, chief information officer of the Southern Nevada Health District, and Grant Walsh, head of IT se...

In this episode, vice president of midsize enterprise services at The Channel Company, Adam Dennison, Samara Lynn, senior editor of MES Computing, Jay Ferro, chief information, technology and product officer at Clario and FranklynCovey global CIO Blaine Carter, discuss the critical topic of AI governance. They explore its importance in business verticals like healthcare, and how organizations can...

In this episode of "Ready Set Mid-Market," hosts Adam Dennison and Samara Lynn are joined by Rory Devine, Vice President of National Technology Accounts at Robert Half Talent Solutions, to discuss the current landscape of the IT job market. The conversation covers the challenges and opportunities for IT leaders and CIOs in the midmarket sector, particularly in the context of Q4 when job changes ar...

Branko Mitkovski is a 27-year veteran of the midmarket as a VP of IT. Mitkovski talks firsthand about navigating his organization through a potentially devastating cyber incident, and how no matter how sophisticated your security defenses may be, don’t be afraid to “trust your gut,” when making security-related decision. In this episode of Ready. Set. Midmarket! co-hosts Adam Dennison and Samara L...

“Harvest now, decrypt later.” This directive will be motivation for an expected surge in an emerging threat: quantum computing cyberattacks. That is according to two experts on the matter who joined co-hosts Adam Dennison and Samara Lynn on the latest Ready. Set. Midmarket! podcast. Lance Smith, co-founder and CEO of Cy4Data Labs, and John E. Young, COO of Quantum eMotion America, lent their exten...

In this episode of Ready. Set. Midmarket! hosts Adam Dennison and Samara Lynn discuss the critical topic of AI poisoning with experts Vrajesh Bhavzar, co-founder and CEO, Operant. AI, and Sarfraz Shaikh, CIO/CISO, One Mesa. The conversation explores the implications of AI adoption in midmarket companies, the security risks associated with AI, and the importance of implementing robust security meas...

In this episode, Adam Dennison and Samara Lynn discuss the emerging concept of shadow AI with Peter Garraghan, co-founder and CEO of MindGuard, a security company that offers red teaming for AI vulnerabilities The conversation delves into the implications of AI used without organizational oversight, the risks associated with shadow AI, and the role of security teams in managing those risks. Peter...

Resource-strapped midmarket organizations often have a single IT executive pulling double duty as CIO and CISO. When is it time to put on your CIO hat versus your CISO one, and what is the best way to juggle both leadership roles? John Michael Gross, CIO and CISO of Cascade Environmental, offers his experience and advice on being the CIO and the CISO. Hosted by Simplecast, an AdsWizz company. See...

This episode delves into the evolving landscape of Cyber Threat Intelligence (CTI), emphasizing its importance for midmarket organizations. Experts Jawahar "Jawa" Sivasankar, who is the president of cybersecurity firm, Cyware, and Christopher J. Walsh, vice president and CISO for Security Mutual Life Insurance Company of New York, discuss the shift from traditional cybersecurity tools to a more th...

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In this episode of Ready, Set, Midmarket, host Adam Dennison and co-host Samara Lynn engage with CIOs Jay Ferro, Eric Tewey, and RC Woodson to discuss the current economic landscape and its impact on IT planning and spending. The conversation explores how organizations are adapting to economic uncertainties, the importance of strategic partnerships, and the role of technology and innovation in nav...