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This summer, an AI agent escaped its testing sandbox, crossed the internet, and spent four and a half days inside another company's production servers. Roughly seventeen thousand actions. No human at the keyboard.
Sounds scary, right? But the same power the attackers have is now available to defenders too. And it's arriving just as the oldest excuse in security runs out.
Jason Maynard, Field CTO for Cybersecurity at Cisco, and Robert Geis, Field CTO for Global Cyber at World Wide Technology, unpack why unpatched vulnerabilities just overtook stolen credentials for the first time in nineteen years, why the fundamentals kept getting deferred, and how IT leaders can put AI to work closing the gap.
Support our sponsor:
This episode is brought to you by Cisco. Learn how to reduce risk, strengthen your security posture, and stay one step ahead of emerging threats at softchoice.com/cisco-security.
In this episode:
• Why the year's most alarming AI attack would have been caught by just doing the basics
• The reframe that turns security from the department of no into the reason the business can move fast
Narrated by guest host Joseph Byer.
#Cybersecurity #AISecurity #ITLeadership #ZeroTrust #MidMarketIT #AgenticAI #ThePodcastForITLeaders
Show Notes & Resources
• Jason Maynard, Field CTO, Cybersecurity — Cisco
• Robert Geis, Field CTO, Global Cyber — World Wide Technology
• Cisco LLM Security Le`aderboard — public rankings of model security, safety and robustness: leaderboard.aidefense.cisco.com/rankings
• Cisco AI Defense — AI asset discovery, model validation, agentic red-teaming: cisco.com/site/us/en/products/security/ai-defense/index.html
• WWT ARMOR (AI Readiness Model for Operational Resilience), developed with NVIDIA: wwt.com/atc-capabilities/ai-readiness-model-for-operational-resilience/overview
• 2026 Verizon Data Breach Investigations Report: verizon.com/business/resources/reports/dbir/
• Black Hat USA 2026 — “The ‘Breaking’ News: The OpenAI–Hugging Face Incident”: youtube.com/watch?v=87DyyMV0kCY
• Cisco security solutions through Softchoice: softchoice.com/cisco-security
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
Your AI bill just stopped behaving like a software bill. For twenty years, IT leaders got very good at counting seats: buy a hundred, pay for a hundred. Then AI swapped the seat for a meter, and the number stopped holding still.
This episode follows the burn from three vantage points: a financial analyst rationing a $250-a-month token budget he tore through in two days; the tech executive who watched enterprise AI bills climb 7x, 10x, 20x; and the IT leader at a 300-person company who refused to solve it with a usage dashboard. Along the way: Meta's leaked internal token leaderboard, Uber blowing its entire annual AI budget by April, and the uncomfortable question of who profits when everyone's told to use more.
In this episode:
Featuring Brian Elliott, CEO of Work Forward; Daryl Dore, Senior Director of IT & Information Security at Higher Logic; and Benjamin, a financial analyst who spoke with us on condition of anonymity.
Support our sponsor:
This episode is brought to you by Sophos MDR. Running Microsoft security tools and drowning in alerts? Sophos MDR's 24/7 experts investigate and stop the real threats.
>>> Learn more at: https://www.sophos.com/en-us/solutions/use-cases/microsoft
#ITLeadership #AICostManagement #SaaSManagement #FinOps #EnterpriseAI #TokenBurn #ITAM
Show Notes & Resources
Referenced in this episode
Guest: Daryl Dore — Higher Logic.
This episode's sponsor: Sophos MDR, in partnership with Softchoice — 24/7 managed detection and response for Microsoft environments. https://www.sophos.com/en-us/solutions/use-cases/microsoft
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
Almost every machine you can buy today is technically an “AI PC.” Which is exactly why the label can’t tell you what to buy. This episode skips the hype and asks the question IT leaders are actually wrestling with: why now, and what happens if you wait? Because two things just landed on the same calendar — the end of Windows 10 support, and an AI-driven memory shortage pushing hardware prices up every quarter — and together they’re quietly taking the refresh decision out of your hands.
In this episode:
Featuring Ivo van Selst, Senior Technical Solutions Architect for AI and Data at Softchoice, a World Wide Technology Company, and Brandon Boone of Dell Technologies’ Client Solutions Group.
This episode is brought to you by Dell Technologies.
Explore Dell’s AI PC lineup — Dell, Dell Pro and Dell Pro Max — and find the right fit for your fleet at softchoice.com/technology-partners/dell
#AIPC #ITLeadership #DeviceRefresh #Windows11 #MidMarketIT #EndUserComputing #TheCatalyst
Show Notes & Resources
Referenced in this episode:
Guests:
Key moments:
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
If you read the headlines, you'd think nearly every major employer marched its workforce back to the office five days a week. The data says otherwise. And so does the human cost when companies push it anyway.
In this episode of The Catalyst, Brian Elliott, CEO of Work Forward, an anonymous 30-year IT veteran and former Marine, and Softchoice's Lisa Walkden lay out what return-to-office mandates are actually about — and what they cost the leaders who issue them.
Here's what you'll take away:
Featuring: Brian Elliott, founder of the Flex Index and CEO of Work Forward; Lisa Walkden, Senior Manager of Workplace Experience at Softchoice, a World Wide Technology Company; and an anonymous IT leader who agreed to share his story on condition we don't name his employer.
#ReturnToOffice #HybridWork #ITLeadership #WorkplaceStrategy #FutureOfWork #FlexIndex #TheCatalyst
Guests
Research & Data Cited
More from Brian
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
There’s a quiet crisis running through IT leadership that nobody names in the meeting: the certainty that you’re in over your head, and that any minute now, someone’s going to find out. It comes with the job. And for women in tech, there’s a second layer underneath.
In this episode of The Catalyst, from Softchoice, a World Wide Technology Company, host Katey Teekasingh sits with three women who’ve lived imposter syndrome from every altitude: an IT director who wasn’t the first pick for her role, a five-time CTO who argues the field itself is the problem, and an MIT scientist who built a whole technology field while the engineering world dismissed her work — then won one of its highest honors.
Their answers about how to lead through doubt without faking it will reframe what most IT leaders quietly carry.
Key takeaways
Guest credentials
Rosalind Picard, ScD — Founder and Director of the Affective Computing Research Group at the MIT Media Lab; co-founder of Empatica and Affectiva; 2026 recipient of the IEEE Medal for Innovations in Healthcare Technology.
Meri Williams — Chief Technology Officer at Pleo; five-time CTO across fintech, retail, banking, and biotech; previously scaled the team that built GOV.UK at the UK’s Government Digital Service.
Julie Szaj — Director of Organizational Change Management at Washington University; 25+ years across education, learning design, and technology leadership.
About Our Sponsor
This episode is brought to you by HP, in partnership with Softchoice. HP helps organizations shape the future of work with AI-powered solutions across devices, printing, and services.
Learn more at https://www.softchoice.com/technology-partners/hp
Hashtags
#TheCatalyst #Softchoice #HP #ITLeadership #ImposterSyndrome #WomenInTech #CTO #DigitalTransformation #MidMarketIT
Show Notes & Resources
Connect with our guests:
Referenced in the episode:
Learn more about HP’s partnership with Softchoice: https://www.softchoice.com/technology-partners/hp
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
Somewhere in your organization, an AI decision is sitting on someone’s desk right now. Who owns it? In most mid-market companies, nobody does — or rather, it’s landed on the IT leader who was already doing three other jobs.
In this episode of The Catalyst, we follow Jeremy Wight, CTO of CareMessage — a patient engagement platform serving 22 million low-income patients across the US — who had to write his organization’s AI policy himself. No committee. No playbook. Just the weight of getting it right for some of the most vulnerable people in the healthcare system.
Alongside Jeremy, we hear from Reid Blackman, author of The Ethical Nightmare Challenge and founder of Virtue, who argues that the standard policy-first approach to AI governance is already broken — and offers a framework any team can implement in weeks, not years. Olivia Gambelin, AI ethicist and author of Responsible AI, reframes the vendor selection question entirely: it’s not about auditing their product, it’s about whether their values align with yours. And Anthony Vinci, former intelligence officer and author of The Fourth Intelligence Revolution, draws an unexpected parallel — between the integrity required of a spy with no rulebook, and the integrity required of an IT leader doing the same.
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This episode is brought to you by HPE.
From AI to data center and network modernization, HPE delivers a cloud-like experience right on your own infrastructure — the full portfolio, from one partner. softchoice.com/technology-partners/hewlett-packard-enterprise
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In this episode:
Featured guests: Jeremy Wight (CTO, CareMessage) • Reid Blackman (Founder/CEO, Virtue) • Olivia Gambelin (AI Ethicist & Author) • Anthony Vinci (CEO, VICO) • Craig McQueen (VP Microsoft Practice, Softchoice)
#AIEthics #ResponsibleAI #ITLeadership #AIGovernance #TheCatalyst #Softchoice #MidMarket #HPE
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Show Notes & Resources
Guests
Sponsor
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
Every IT leader has a “day one” story. The moment they opened the server closet, logged into the admin console, or reviewed the vendor contracts and realized the job they were hired for isn’t the job they actually have.
In this episode of The Catalyst, we follow Chris Schopf, an IT operations team lead who walked into a new job to find twelve-year-old servers, two unfinished infrastructure projects, and a team that had been poached by the outgoing manager. Then we hear from Leon Adato, a 37-year IT veteran who’s made a career of walking into other people’s messes, and Ned Bellavance, a former consultant who warns that not every mess is actually a mess. Some of it is “purposeful chaos” you just don’t understand yet.
What you’ll learn:
Featuring:
Chris Schopf — IT Security Architect
Leon Adato — Principal Technical Marketing Engineer, Cribl
Ned Bellavance — Founder, Ned in the Cloud | Podcast Host
From Softchoice, a World Wide Technology company — this is The Catalyst.
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
After our biggest season ever — nearly 80,000 downloads, a top 2% global ranking, and a documentary-style approach unlike any other show in B2B tech — host Katey Teekasingh is back to set up what's coming next.
Season 8 takes on the questions mid-market IT leaders are quietly wrestling with right now: the rise of accidental AI ethics officers. The imposter feeling that follows even the most senior leaders. The SaaSpocalypse threatening to undo years of cost optimization. What happens when you inherit a mess. The new realities of security and the return to the office. And a lot more.
We're bringing you the human side of IT — told like a documentary, not a Q&A.
New episodes every second Wednesday. Only on The Catalyst — from Softchoice, a World Wide Technology company.
Subscribe now and join the thousands of IT leaders already listening.
Listen to back episodes and more: https://www.softchoice.com/podcast
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
For decades, building software meant doing eighty percent of the hard work before you had anything to show for it. AI just flipped that equation. And it's creating a risk nobody planned for.
In this episode of The Catalyst, host Katey Teekasingh explores vibe coding — the technology that lets anyone build software by describing what they want in plain language. It was named Collins Dictionary's 2025 Word of the Year. It's already inside your organization. And in late 2025, it might have taken down Amazon's own cloud for thirteen hours.
Three experts break down where vibe coding genuinely helps, where it's dangerous, and what to put in place before it touches anything that matters.
In This Episode
Guests
Support Our Sponsor
This episode of The Catalyst is brought to you by Veeam Data Cloud Vault — fully managed, secure cloud storage for your backups, with no surprise bills and zero configuration headaches.
Sign up for their AWS Demo Series and see it in action:
https://veeam.com/aws-native-backup-demo-series.html
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
What got you here won't get you there. For most IT leaders, the path to the top was paved with expertise — knowing the systems, owning the decisions, having the answers. But something happens when that playbook stops working. Not a crash. Not a failure. Just a quiet plateau that tells you something needs to change.
In this episode of The Catalyst, we explore what's on the other side of that wall: a shift toward curiosity, empowerment, and a fundamentally different way of leading. Featuring leadership coach Kirsten Schmidtke, curiosity researcher Dr. Deb Clary, and Benevity VP of Engineering Rob Woolley — three voices who all landed in the same place.
What you'll take away:
Featuring: Rob Woolley, VP Core Platform & Data Engineering at Benevity | Kirsten Schmidtke, Leadership Coach & Growth Advisor | Dr. Deb Clary, Author of The Curiosity Curve (Fast Company Press)
Learn more about Kirsten at kirstenschmidtke.com
Take Deb's curiosity assessment at debraclary.com
#ITLeadership #MidMarketIT #TheCatalyst #CuriousLeadership #Softchoice #LeadershipDevelopment #FutureOfIT
The Catalyst by Softchoice is the podcast dedicated to exploring the intersection of humans and technology.
From the publisher's feed
A documentary-style podcast about how IT leaders tackle high-stakes transformations.
Each episode weaves together real voices, expert insights, and compelling narratives that reveal…
Season 7: "Small Teams, Big Dreams" explores the human stories behind IT transformations—from AI adoption experiments to burnout crises, from toxic job markets to infrastructure decisions that matter. These aren't polished case studies. These are authentic accounts from IT professionals navigating the same impossible gaps between expectations and resources that you face every day.
From Softchoice, a World Wide Technology company.

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