Podcast
Ready, Set, Midmarket!
Hosted by Samara Lynn, Adam Dennison · EN
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.
21episodes
Episodes
Newest firstAll episodes
From VMware to Azure: How a Midmarket Credit Union Cut Costs & Built Resilient Hybrid IT
2w ago00:23:07Tap to summarizeWhat 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. Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.
Transcribe →Windows 11 Update Delays: The Hidden Cyber Resilience Risk for Midmarket IT
3w ago00:14:04Tap to summarizeMicrosoft 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 for information about our collection and use of personal data for advertising.
Transcribe →Here's What Happens When Midmarket's AI Adoption Strategy Is 'Active' But 'Informal'
Apr 1700:18:34Tap to summarizeMidmarket 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.
Transcribe →Midmarket CIO Priorities for 2026 - Why AI Can’t Move Faster Than Your Data Security
Mar 1300:13:45Tap to summarizeIn 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.
Transcribe →Ready.Set.Midmarket!: CISO Strategies In 2026
Mar 600:28:26Tap to summarizeIn 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.
Transcribe →AI Training & Certifications Midmarket IT Leaders Need in 2026 | Ready.Set.Midmarket!
Feb 200:29:42Tap to summarizeShadow 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.
Transcribe →Ready.Set.Midmarket!: The Midmarket's Tech Road Ahead In 2026
Jan 2300:33:32Tap to summarizeExecutive 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.
Transcribe →AI Governance For The Midmarket
Dec 1900:27:42Tap to summarizeIn 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.
Transcribe →Ready.Set.Midmarket! Podcast: Rory Devine, VP, Robert Half Technology Solutions On A ‘No Fire, No Hire’ IT Job Market
Oct 3000:26:27Tap to summarizeIn 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.
Transcribe →Trust Your Gut During Cyberattacks
Sep 1200:24:03Tap to summarizeBranko 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.
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