Ready, Set, Midmarket!

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. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 Integrated Solutions Chris Boehm - Field CTO, Zero Networks Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 information about our collection and use of personal data for advertising.

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 security infrastructure and operations at Flow Control Group, join Adam Dennison and Samara Lynn to discuss the strategies they are using to successfully implement AI in their organizations, and what they are prioritizing this year. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 effectively implement AI governance frameworks no matter the industry. The conversation emphasizes the need for collaboration across departments, the significance of data governance, and the balance between innovation and compliance. The discussion also focuses on practical steps for midmarket leaders to begin their AI governance journey and highlights the importance of monitoring AI models to ensure compliance and effectiveness. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 are prevalent. Devine shares insights on the impact of AI and automation on traditional roles, the importance of reskilling and upskilling, and the rise of fractional executive roles. The discussion also touches on the evolving expectations of CEOs, the role of private equity in the industry, and the significance of personal relationships in recruiting. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 Lynn speak with Mitkovski on the importance of trusting instincts when it comes to security alerts, the negotiation process with threat actors, and the need for midmarket companies to bolster their cybersecurity measures. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

“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 extensive expertise on the subject of Q-Day and post-quantum computing (PQC) encryption. Both describe how threat actors are currently harvesting encrypted data through cyberattacks. While the bad guys don’t have the means yet to decrypt this data, in the very near future they will have a way—through quantum computing. The time frame for when threat actors will have relatively easy and widespread access to quantum computing power is what is known as “Q-Day.” Smith and Young discuss what Q-Day is, when it’s expected to arrive, the catastrophes that can happen when hackers are able to break traditional encryption, and what midmarket leaders should do now to prepare. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 measures to combat potential threats. The guests share insights on the current landscape of AI security, the challenges faced by organizations, and the solutions offered by Operant.AI to protect against AI poisoning attacks. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 also shares insights from a recent survey on AI usage among cybersecurity professionals, highlighting the need for controls and visibility in AI adoption. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 threat-centric approach, the integration of AI in cybersecurity, and the challenges of tool saturation. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

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 navigating challenges. The CIOs share insights on project management, cybersecurity concerns, and team dynamics during turbulent times, emphasizing the need for flexibility and proactive planning in their organizations. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of Ready, Set, Midmarket! the discussion revolves around agentic AI, its implications for midmarket organizations, and the associated security challenges. Daryan "D" Dehghanpisheh, president and co-Founder of Protect AI, shares insights on the rapid adoption of AI agents, the unique risks they pose, and the importance of integrating security measures as organizations navigate this evolving landscape. The conversation emphasizes the need for midmarket companies to adapt quickly, understand the implications of AI on labor, and develop robust security frameworks to manage the risks associated with AI deployment. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Technical debt costs organizations nearly $3 million a year. Tech debt accumulates when companies take short cuts when writing code, by not updating legacy hardware, and for other reasons. Adam Dennison, Vice President, Midsize Enterprise Services at The Channel Company, and Samara Lynn, senior editor of MES Computing, speak with Ken Knapton, a seasoned IT leader and the author of Unveiling Tech Debt: A Business Leaders Guide to Measuring and Managing Enterprise Tech Debt Leverage, about how midmarket IT leaders can recognize and address tech debt. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode: The Girl Scouts have great cookies, but did you know they also have great technology? Join us in our discussion with Michael Pompey, the Chief Information and Transformation Officer of the Girl Scouts of Eastern Pennsylvania. Hosts Adam Dennison and Samara Lynn speak with Pompey on AI's impact on corporate culture, the significance of "soft skills" for IT executives as well as the importance for a human connection in tech, policy making, and more. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.

Welcome to the Ready.Set.Midmarket! podcast where we discuss the latest news, expert insights, tips and trends for midmarket IT leaders, hosted by Adam Dennison, VP of Midsized Enterprise Services (MES) at The Channel Company, and Samara Lynn, senior editor of MES Computing. This episode features Jason Frame, Chief Information Officer of the Southern Nevada Health District, and Grant Walsh, head of IT security infrastructure and operations at Flow Control Group. In this edition, we talk tech predictions for IT in 2025, how these midmarket IT leaders are using AI, concerns about DeepSeek, cybersecurity strategies, customer service bots that mimic humans so well down to throat clearing, and more! Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.