The Digital Executive

In this episode of The Digital Executive Podcast, host Brian Thomas sits down with Jen Grogono, founder and CEO of uStudio, to explore why the future of enterprise training and internal communications looks a lot more like Spotify than a company intranet. Jen opens with the founding story of ON Networks in 2006, where the challenge of syndicating original content across a hundred different endpoints — each with different metadata, formats, and technical requirements — planted the seed for what would become uStudio. When she saw enterprises building massive libraries of training and marketing content with no infrastructure to manage or measure them, the pivot was clear. She breaks down why the measurement layer is so critical to enterprise buyers: it is not enough to send a message, leaders need to know what is landing, who tuned out at the twenty percent mark, and what is actually changing behavior. That feedback loop, built on a secure instrumented platform inside corporate networks, is what separates content that moves people from content that gets ignored. She then addresses AI's role in two directions simultaneously — as the subject of urgent workforce change management that demands better communication, and as the engine making content creation, personalization, and discovery faster and more targeted than ever. Her product AutoCast turns corporate documents and knowledge bases into audio, so AI can surface the right three-second clip or five-minute deep dive exactly when a worker needs it. She closes with a vision of the enterprise as an always-on Spotify-like network — personalized to each worker's role, consumption habits, and learning needs, delivered through their phone at any idle moment — and makes the case that the companies that build that infrastructure now will be the ones whose messages actually land when it matters most.

If you liked what you heard today, please leave us a review - Apple or Spotify.

Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Digital Executive Podcast, host Brian Thomas sits down with Kevin Pickhardt, Executive Chairman of Pharos Systems International, to make the case that one of the most overlooked vulnerabilities in enterprise IT is sitting right there in the corner of every office floor — the printer. Kevin opens with a career that began at Xerox forty years ago and traces the surprisingly consistent thread through every transformation since: printing never went away, but the infrastructure managing it never kept up. He explains why printing has been uniquely resistant to modernization — historically owned by facilities rather than IT, split across drivers, print servers, endpoints, and physical documents with no single accountable owner, and architecturally built on trust rather than zero trust. A printer today accepts any file from anyone who can reach it on the network, which is precisely the opposite of how modern security is supposed to work. He then walks through how hybrid work and COVID fundamentally changed print behavior — breaking the personal relationship between employee and device, driving printing into home networks enterprises couldn't control, and forcing organizations to rethink printing not as a connection from desk to nearby printer but as a cloud-based queue accessible from anywhere. He closes with a clear vision of what modern printing infrastructure has to become: cloud native, user-centric and identity-first, integrated with broader IT systems rather than siloed, and secured end-to-end with data loss prevention that can flag when someone suddenly starts printing sensitive financial documents. The paperless office, Kevin notes, was a prediction made forty years ago and still hasn't arrived — and the organizations that accept print as a permanent fixture and modernize it accordingly will be the ones that close the security gap before someone else exploits it.

If you liked what you heard today, please leave us a review - Apple or Spotify.

Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Digital Executive Podcast, host Brian Thomas sits down with Shannon Flanagan, founder and CEO of Retail Women in Tech, to make a case that the most important thing missing from most AI transformation efforts isn't better technology — it's the right people in the room. Shannon opens with a career that started at 18 folding jeans and evolved through merchandising, consulting at Accenture, and leadership roles at Gap, Lands' End, and Macy's, shaped throughout by a single question she discovered at 25: what does it take to create the conditions where people love what they do every day? That question led her to organizational design, change management, and eventually to founding a nonprofit she describes as the hardest, poorest, and most fulfilling chapter of her life. She built Retail Women in Tech not to create another exclusive senior women's network, but to get more women — at every level, function, and age — into the rooms where AI decisions are being made, because she believes the qualities women have historically been told to downplay are exactly the ones the AI era will reward most. On change management, Shannon introduces a framework as simple as it is powerful: potential minus interference equals performance, and argues that most AI transformations fail because leaders lead with technology and ROI instead of starting with human readiness, trust, and psychological safety. She closes with a forward-looking vision of what success will look like in retail and beyond — not functional expertise, but judgment, discernment, ethics, and connection — and a challenge to women entering the field to stop waiting until they feel ready for AI roles and start recognizing that what they bring is exactly what the future needs.

If you liked what you heard today, please leave us a review - Apple or Spotify.

Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Digital Executive Podcast, host Brian Thomas sits down with Allen Dine, Chief Business Officer at Care2You, to explore what it actually takes to deliver emergency and hospital-level care inside someone's home — and how AI is making that possible at scale across one of the most complex urban environments in the world. Allen opens by tracing a career defined by a refusal to wait for someone else to solve the problem, from learning SQL to build his own data warehouse to deploying AI voice agents for patient intake — because in home care, if you want change, you have to build it yourself. He then walks through how Care2You uses voice AI for the highest-stakes first contact in healthcare: patient intake screening. The agents collect vitals, demographics, and recent history, cut a five-minute clinical call to under two minutes, and flag red flags — but they never make clinical decisions. Every conversation is fully audited so clinicians can review exactly what happened before stepping in, keeping the human always in the loop and the process never a black box. The dispatch and routing challenge gets equal attention: matching the right clinician to the right patient across New York City's five boroughs in real time, accounting for traffic, acuity, and a patient load that isn't fully known until the day unfolds. AI compresses what used to take ten minutes of dispatcher judgment into seconds, presenting ranked options that humans can override and adjust. Allen closes with a vision of hospital-at-home that goes beyond just moving the site of care — arguing that the real opportunity is educating patients about what conditions can be safely and comfortably treated at home, so that recovery happens surrounded by family, pets, and familiar routines rather than hospital walls, at lower cost to everyone involved.

If you liked what you heard today, please leave us a review - Apple or Spotify.

Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of The Digital Executive Podcast, host Brian Thomas sits down with Furkat Kasimov, London-based entrepreneur, angel investor, and author, to explore what it takes to build and invest wisely in the AI era — before the crowd figures it out. Furkat opens with a origin story that predates the current AI boom by a decade, tracing his first investment to an InsureTech conference where he spotted a deepfake detection company called PinDrop Security and recognized that every dangerous technology creates a market for its antidote. That insight became the founding logic of Applayerai, a venture studio built around predicting what solutions large corporations will need in five to ten years — and building them before those corporations think to ask. He then unpacks the philosophy behind his book Don't Do This, explaining why he focused on cataloguing over 150 business mistakes rather than celebrating success stories: timing and luck can't be replicated, but someone else's mistakes can be avoided. He closes with sharp advice for executives navigating the AI stack: treat foundation models like cloud providers and build for model independence so you can swap them out without rebuilding everything; match model cost to task complexity rather than defaulting to the most powerful option for everything; and always measure the cost of completing a workflow so you can actually optimize it. His parting message cuts through the noise simply — don't lose sight of what makes your business great, treat AI as a utility, and build the knowledge base that lets your agents keep improving over time.

If you liked what you heard today, please leave us a review - Apple or Spotify.

Learn more about your ad choices. Visit megaphone.fm/adchoices