Automate or Die Trying

“How John Shende Is Redefining AI Security, Agentic Governance, and the New Insider Threat”

Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Jon G Shende, CTO of Data Security & AI and Global VP of SecOps at Sutherland, to explore what it really takes to secure AI at enterprise scale. Jon shares how he helped rebuild a modern AI-driven security stack in partnership with Google Security, retiring legacy systems and standing up a new, machine-learning-powered operation from the ground up. He also reflects on his early work coining “cloud forensics as a service,” a concept that anticipated many of today’s cloud security challenges. The conversation examines the rise of agentic AI and why traditional governance models are no longer sufficient. Jon explains how AI is becoming the new insider threat, not because it’s malicious, but because of the level of access, autonomy, and trust organizations are giving it. They also unpack real-world lessons from large-scale security transformations, including the challenges of aligning stakeholders, managing risk, and ensuring data integrity across complex systems. Jon emphasizes that while automation and AI create massive opportunities, they also require strong fundamentals in access control, policy enforcement, and auditability. For leaders building in today’s AI-driven world, Jon highlights the importance of collaboration, practical security design, and responsible adoption of emerging technologies. Key Takeaways: * AI is becoming the new insider threat due to its trusted access and speed at scale * Governance must evolve to operate at the workflow level, not just static control points * Overprivileged AI agents increase the risk of data exposure and misuse * Automation without strong fundamentals can amplify security failures * The ROI of security lies in preventing incidents, not generating revenue * Large-scale transformations require alignment across technical and business stakeholders * Great leadership is about enabling teams, not taking the spotlight Connect with Jon G Shende: * LinkedIn: https://www.linkedin.com/in/jonshende [https://www.linkedin.com/in/jonshende] * Website: https://cloudfraas.com [https://cloudfraas.com] * Blog: https://jonshende.blogspot.com/view/magazine [https://jonshende.blogspot.com/view/magazine] Listen Now & Subscribe: Apple Podcasts [https://podcasts.apple.com/us/podcast/automate-or-die-trying/id1858617259], Spotify [https://open.spotify.com/show/7JJN8GliYhaECVEduFcvmW?si=99700a8227cb47eb], Amazon Music [https://music.amazon.com/podcasts/e7e24a5f-61e0-4c7f-8af1-be7b87cbdc02/automate-or-die-trying], or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com [https://cybersecurityprivacy.com/] Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

“How Ryan Donahue Secures Millions of Devices and Billions of Transactions at Comcast”

Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Ryan Donahue, Senior Director of Cybersecurity at Comcast. Ryan leads vulnerability management, asset inventory, compliance, and fraud detection across one of the largest and most complex networks in the world, supporting millions of internal assets and more than 100 million customer devices. Ryan shares how his background as a software engineer shaped his approach to security leadership. Instead of relying solely on vendor tools, he often builds internal systems to solve security challenges at massive scale, including credential management platforms handling billions of transactions per day and automation frameworks designed to protect telecom infrastructure. The conversation explores the realities of securing large-scale telecom systems, where pushing updates or configuration changes can impact millions of devices simultaneously. Ryan discusses the challenge of maintaining visibility across massive infrastructure and how his team works to identify unknown assets and reduce operational risk. Ryan also explains why automation must be implemented carefully in security environments. While automation enables scale, poorly designed systems can amplify vulnerabilities. His approach focuses on building secure defaults into platforms so engineering teams can move quickly while maintaining strong security standards. For security leaders and engineers, Ryan emphasizes the importance of strong debugging skills, clear security metrics, and designing platforms that make security scalable across large engineering organizations. Key Takeaways: 1. Security at telecom scale requires deep engineering and custom tooling 2. Asset visibility is the foundation of an effective security program 3. Automation must be designed carefully to avoid amplifying risk 4. Security platforms should simplify protection for developers 5. Security reporting should focus on patterns rather than raw vulnerability counts 6. Strong debugging and system-level thinking remain essential skills Connect with Ryan Donahue: 1. LinkedIn: https://www.linkedin.com/in/ryan-donahue-28324a5https://www.linkedin.com/in/ryan-donahue-28324a5 [https://www.linkedin.com/in/ryan-donahue-28324a5] 2. Website: https://rydonahue.comhttps://rydonahue.com [https://rydonahue.com] Listen Now & Subscribe: Apple Podcasts [https://podcasts.apple.com/us/podcast/automate-or-die-trying/id1858617259], Spotify [https://open.spotify.com/show/7JJN8GliYhaECVEduFcvmW?si=99700a8227cb47eb], Amazon Music [https://music.amazon.com/podcasts/e7e24a5f-61e0-4c7f-8af1-be7b87cbdc02/automate-or-die-trying], or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com [https://cybersecurityprivacy.com/] Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

“How Art Pugach Turns AI and Co-Pilot into Practical Business Automation”

Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Art Pugach, CTO of Key Associates and Microsoft MVP, recognized for his work with M365 Co-Pilot. Art shares insights from his 27-year career building ERP, CRM, AI, and automation solutions, and discusses how organizations can move beyond hype to apply AI practically. The conversation explores the importance of understanding human workflows before deploying automation, practical examples of AI creating knowledge bases and streamlining order processing, and the role of AI as an assistant rather than a replacement. Art also highlights lessons learned from early ERP implementations, managing AI credit limits, and showing employees how to effectively use AI tools. For business leaders, IT professionals, and tech enthusiasts, Art emphasizes starting with use cases, combining human oversight with AI agents, and leveraging automation to free up resources for higher-value work. Key Takeaways: * AI and automation succeed when human workflows are well-defined * Co-Pilot and AI agents can dramatically reduce repetitive tasks * Knowledge bases and help desk automation save months of work in days * Human oversight is critical; AI cannot read minds * Understand AI licensing and credit limits to avoid hidden costs * Focus on practical use cases to demonstrate value Connect with Art Pugach: * LinkedIn: https://www.linkedin.com/in/art-pugach-8144b236 [https://www.linkedin.com/in/art-pugach-8144b236] * Key Associates: https://www.keyassociates.com [https://www.keyassociates.com] * Podcast: When in Doubt Reboot – https://whenindoubtreboot.com Listen Now & Subscribe: Apple Podcasts [https://podcasts.apple.com/us/podcast/automate-or-die-trying/id1858617259], Spotify [https://open.spotify.com/show/7JJN8GliYhaECVEduFcvmW?si=99700a8227cb47eb], Amazon Music [https://music.amazon.com/podcasts/e7e24a5f-61e0-4c7f-8af1-be7b87cbdc02/automate-or-die-trying], or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com [https://cybersecurityprivacy.com/] Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

“How David VonThenen Designs Production-Ready AI Systems and Agent Architectures”

Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with David VonThenen, an AI/ML engineer and systems architect focused on building reliable AI systems that move beyond demos into real-world production. David shares insights from his background in infrastructure and distributed systems, explaining why strong architecture, observability, and governance are critical when deploying AI at scale. The conversation explores hybrid retrieval approaches beyond simple vector search, the rise of multi-agent AI systems, and the growing need for monitoring and safeguards as AI tools become more autonomous. For founders, engineers, and technical leaders, David emphasizes a practical approach: design systems carefully, prioritize reliability, and continuously validate AI models in production environments. Key Takeaways: * Start with solid system architecture before scaling AI models * Hybrid retrieval strategies often outperform pure vector search * Multi-agent architectures allow modular, scalable AI workflows * Observability and governance are critical for production AI systems * Adversarial prompts highlight the need for strong safeguards * Infrastructure design still matters as much as model quality Connect with David VonThenen: * LinkedIn: https://linkedin.com/in/davidvonthenen [https://linkedin.com/in/davidvonthenen] * GitHub: https://github.com/dvonthenen [https://github.com/dvonthenen] * Twitter/X: https://twitter.com/dvonthenen [https://twitter.com/dvonthenen] * Personal Website: https://davidvonthenen.com [https://davidvonthenen.com] Listen Now & Subscribe: Apple Podcasts [https://podcasts.apple.com/us/podcast/automate-or-die-trying/id1858617259], Spotify [https://open.spotify.com/show/7JJN8GliYhaECVEduFcvmW?si=99700a8227cb47eb], Amazon Music [https://music.amazon.com/podcasts/e7e24a5f-61e0-4c7f-8af1-be7b87cbdc02/automate-or-die-trying], or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com [https://cybersecurityprivacy.com/] Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

“How Oleg Danyliuk Builds Real-Time AI for Sales and Automation Across Continents”

Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Oleg Danyliuk, CEO of Duanex and CTO of Insyghtful.ai. Oleg combines nearly two decades of enterprise software experience with a deep focus on AI-driven automation and real-time insights, helping businesses scale efficiently while keeping human judgment in the loop. Oleg shares his journey from a Java developer in Ukraine to leading distributed engineering teams across continents, building high-load banking systems, ticketing platforms, and enterprise service buses. He discusses founding Duanex in 2016 to provide clients with high-value automation solutions, emphasizing transparency, delivering real outcomes, and prioritizing client relationships over short-term revenue. The conversation explores how Oleg applies enterprise-grade rigor to AI agent development. He walks through his work deploying AI for lead validation at Duanex and developing Insyghtful.ai, a platform that reads the emotional temperature of sales calls in real-time, providing actionable guidance to reps while balancing speed, latency, and usability. Oleg explains the challenges of working with incomplete or messy data, handling human-AI collaboration, and managing distributed teams under extreme conditions, including operating with developers in active war zones in Ukraine. Oleg also shares insights on scaling AI responsibly: start small, focus on meaningful impact, avoid automating everything, and use external APIs like OpenAI’s Gemini to test quickly before committing to full custom models. He emphasizes that AI should augment human intelligence rather than replace it, highlighting the ongoing need for maintenance, monitoring, and cultural context when interpreting emotional signals in conversations. For founders, technical leaders, and AI enthusiasts, Oleg’s advice is clear: focus on solving high-value problems incrementally, maintain transparency with clients, and continuously validate your models in production to ensure real-world efficacy. Key Takeaways: 1. Start small with AI automation—test single steps before scaling 2. Use APIs for low-cost experimentation before building custom models 3. Real-time AI requires low latency (sub-second) for actionable insights 4. AI augments humans; it does not replace nuanced human judgment 5. Distributed engineering teams can maintain high performance even under extreme conditions with proper infrastructure and human connection 6. Data quality is an ongoing effort, not a one-time cleanup 7. Transparency with clients builds long-term trust and drives referrals Connect with Oleg Danyliuk: 1. LinkedIn: https://www.linkedin.com/in/oleg-danyliukhttps://www.linkedin.com/in/oleg-danyliuk [https://www.linkedin.com/in/oleg-danyliuk] 2. Company: https://duanex.comhttps://duanex.com [https://duanex.com] Listen Now & Subscribe: Apple Podcasts [https://podcasts.apple.com/us/podcast/automate-or-die-trying/id1858617259], Spotify [https://open.spotify.com/show/7JJN8GliYhaECVEduFcvmW?si=99700a8227cb47eb], Amazon Music [https://music.amazon.com/podcasts/e7e24a5f-61e0-4c7f-8af1-be7b87cbdc02/automate-or-die-trying], or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com [https://cybersecurityprivacy.com/] Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.