Ready, Set, Midmarket!

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.