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.
24episodes
Episodes
Newest firstAll episodes
Your AI Bill Is Coming: Why CIOs Are Worried About SaaS Costs
1w ago00:26:34Tap to summarizeThe 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 for information about our collection and use of personal data for advertising.
Transcribe →Midmarket IT Must Adapt--What Leaders Need to Do Before 2027
4w ago00:24:41Tap to summarizeWhat 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 for information about our collection and use of personal data for advertising.
Transcribe →Zero Trust: What Does It Mean Exactly, In Practice?
Jul 100:23:40Tap to summarizeIn 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 collection and use of personal data for advertising.
Transcribe →From VMware to Azure: How a Midmarket Credit Union Cut Costs & Built Resilient Hybrid IT
May 1900:23:07Tap 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
May 1400:14:04Tap 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.
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