Events

How AI is Transforming Organizations and Cyber Roles

Join leading cyber experts for an interactive discussion on how cybersecurity organizations are adapting to a rapidly evolving landscape.

The Cyber Guild’s Virtual Leadership Roundtables bring together national leaders and expert voices for candid, high-value conversations at the intersection of digital and cyber security, workforce, and emerging technology.

In the first of a two-part series, we’ll explore how AI is transforming organizations and redefining cyber roles, and what that means for leadership today.

Moderated by Will Markow, Founder and CEO of FourOne Insights, this virtual live session is designed for leaders across all sector to exchange perspectives, challenge assumptions, and surface practical insights with peers navigating the same shifts.

As AI-driven capabilities and automated workflows reshape expectations, the question is no longer if roles will change, but how quickly organizations can adapt their talent strategies to keep pace.

Don’t miss out on this powerful cyber leadership meetup!

Date & Time:

📅Wednesday, May 20
🕒12:30-1:30 PM EST
💻 Virtual


Will Markow
(Moderator)
Founder & CEO, FourOne Insights

Will Markow is an internationally recognized expert on the future of work and the Founder and CEO of FourOne Insights, a research and advisory firm focused on the impact of emerging trends and technologies on the workforce.

Will has advised hundreds of companies, technology vendors, training providers, workforce development organizations, government agencies, and multiple White House administrations on key issues related to the future of work, skills-based hiring, and related topics. His research has been featured in the New York Times, Wall Street Journal, CNBC, and numerous other national media outlets. He has also testified before Congress on growing the cybersecurity talent pipeline.

Will previously spent 12 years with Lightcast, where he oversaw their workforce consulting and research team. Will also oversaw the development of CyberSeek.org – a cybersecurity career exploration portal frequently cited by national media outlets and multiple presidential administrations.

Brad Rumph
Field CTO, Tines

Brad Rumph is the Field CTO at Tines, where he empowers organizations to bridge the gap between complex IT operations, security demands, and human potential through agentic AI and intelligent workflows. With a career spanning leadership roles at Google Cloud, Amazon, Salesforce, and IBM Software Group, Brad specializes in building scalable, secure architectures that drive real-world impact. A technical visionary who thrives on execution, he is dedicated to fostering high-performing teams and exploring the practical applications of responsible agentic AI.

Brad earned a BS in Finance and Computer Science from Oklahoma State University, followed by an MS in Telecommunications and Computer Science from Southern Methodist University.
Dr. Jennifer Blum
Director of AI and Analytics, Huntington Ingalls Industries (HII)

Dr. Jennifer Blum is the second Black woman to earn a Ph.D. in Astrophysics from the University of Michigan, with early expertise in satellite systems, aircraft radar, and black hole physics. She has since transitioned into a recognized leader in cybersecurity, AI, and advanced data science. Her career includes roles as a government data scientist developing machine learning algorithms for cybersecurity missions, senior IT strategist, and Director-level data scientist focused on cutting-edge infrastructure and business solutions. Dr. Blum currently serves as Director of AI and Analytics at Huntington Ingalls Industries (HII). There, she leads large-scale AI initiatives across defense and critical infrastructure, helping secure and manage programs exceeding $100 million.

Dr. Blum is the Founder of JenAI Group LLC, a clarity-first, human-centered AI consultancy dedicated to making AI clear and understandable. It’s a trusted partner in innovation, distilling complexity into insight and delivering ethical, actionable solutions for stakeholders at every level, from the C-suite to frontline teams. The firm specializes in ethical AI, trustworthy AI, cybersecurity, and predictive analytics to address complex societal and infrastructure challenges. Its current focus areas include AI innovation in public health, decentralized systems, and pharmaceutical supply chain strategy.

Outside of her technical achievements, Dr. Blum is a professional voice actress and has lent her talents to radio commercials, audiobook narrations, and virtual reality experiences. She is passionate about mentoring diverse talent and fostering inclusive innovation across STEM fields.

Dr. Yolanda Reid
Vice President, Cybersecurity, The MIL Corporation

Dr. Yolanda C. Reid is the Vice President of Cybersecurity at The MIL Corporation where she leads innovation in cybersecurity, responsible AI, and quantum readiness for national security missions. With over two decades of experience, she spent 21 years with the U.S. Department of Defense and has held senior leadership roles at EverWatch (Booz Allen Hamilton), Raytheon BBN, and IBM Federal, shaping advanced cyber and emerging technology capabilities across the defense and intelligence community.

Dr. Reid holds a Bachelor of Engineering in Electrical Engineering from Vanderbilt University and a Ph.D. in Information Technology with research focused on AI adoption in the U.S. aerospace and defense industry.

Jessie Skibbe
Principal Security Strategist, Amazon Web Services

In collaboration with:

Wednesday, May 20, 2026
12:30 PM