Steve Clayton has emerged as a retro renegade at Microsoft, seeking to show that print books and magazines still matter in the digital age. Now he’s turning the page on his own career.

Clayton, most recently Microsoft’s vice president of communications strategy, announced Monday morning that he’s leaving the Redmond company after 28 years to become Cisco’s chief communications officer, starting next month, reporting to CEO Chuck Robbins.

“In some ways, it feels like a full-circle moment: my career began with the rise of the internet and the early web — and Cisco was foundational to that story,” he wrote on LinkedIn, noting that AI makes infrastructure and security all the more critical.

He leaves behind two passion projects: 8080 Books, a Microsoft publishing imprint focused on thought leadership titles, and Signal, a Microsoft print magazine for business leaders. He said via email that both will continue after his exit. He’s currently in the U.K. wrapping up the third edition of Signal. 

Clayton joined Microsoft in 1997 as a systems engineer in the U.K., working with commercial customers including BP, Shell, and Unilever. He held a series of technical and strategy roles before moving to Seattle in 2010 to become “chief storyteller,” a position he held for 11 years.

That put Microsoft ahead of the curve on a trend now sweeping corporate America: The Wall Street Journal reported last week that “storyteller” job postings on LinkedIn have doubled in the past year.

As chief storyteller, Clayton led a team of 40 responsible for building technology demonstrations for CEO Satya Nadella, helping shape Microsoft’s AI communications strategy, running the corporate intranet, and overseeing social media and broader culture-focused campaigns.

In 2021, Clayton moved into a senior public affairs leadership role. During that period, he was involved in companywide efforts related to issues including AI policy and the Microsoft–Activision deal, before transitioning to his current communications strategy role in 2023.

In his latest position, Clayton has focused on using AI to transform how Microsoft runs its communications operations, reporting to Chief Communications Officer Frank Shaw.

This episodes diverges from our traditional fare. I’ve reviewed the 49 previous editions and picked (IMHO) the coolest code, best prose & my favorite podcast episode from each month!

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Featuring:

• Jerod Santo – GitHub, LinkedIn, Mastodon, X

Guest:

• Bruce Schneier

Topics:

• Do you believe that AI is going to end up being a net improvement for defenders or attackers?  Is short term vs long term different?
• We're excited about the new book you have coming out with your co-author Nathan Sanders "Rewiring Democracy".  We want to ask the same question, but for society: do you think AI is going to end up helping the forces of liberal democracy, or the forces of corruption, illiberalism, and authoritarianism? 
• If exploitation is always cheaper than patching (and attackers don't follow as many rules and procedures), do we have a chance here? 
• If this requires pervasive and fast "humanless" automatic patching (kinda like what Chrome does for years), will this ever work for most organizations?
• Do defenders have to do the same and just discover and fix issues faster? Or can we use AI somehow differently?
• Does this make defense in depth more important?
• How do you see AI as changing how society develops and maintains trust? 

Resources:

• "Rewiring Democracy" book
• "Informacracy Trilogy" book
• Agentic AI's OODA Loop Problem
• EP255 Separating Hype from Hazard: The Truth About Autonomous AI Hacking
• AI and Trust
• AI and Data Integrity
• EP223 AI Addressable, Not AI Solvable: Reflections from RSA 2025
• RSA 2025: AI's Promise vs. Security's Past — A Reality Check