PRIVATE EXECUTIVE ROUNDTABLE – CHICAGO – OCTOBER 2026

Bridging the Human vs. Machine Reputation Gap

How AI narratives diverge from stakeholder perceptions, why this is becoming the next frontier of corporate risk – and what companies should do about it.

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Join Caliber and MWW for an exclusive roundtable where senior leaders across Comms, Corporate Affairs, Risk/Legal, and Marketing will explore how to measure and close the growing gap between AI-generated narratives and stakeholder perceptions—and what that means for the future of reputation management.
📅 Date: October 15, 2026
📍 Location: MWW HQ, Chicago
 

(Details subject to final confirmation — we’ll notify registrants of any changes.)

Artificial intelligence is fundamentally changing how organizations are discovered, interpreted and trusted. AI-powered search and generative platforms are increasingly shaping the first impression stakeholders form about companies, often before they visit a website, speak with an employee or engage with the brand directly.

While organizations are investing heavily in AI optimization, search and content strategies, many are overlooking a more fundamental question: Do these AI-generated narratives accurately reflect how your most important stakeholders actually perceive your organization?

Join a cross-functional group of senior leaders for an open, peer-level discussion on why this emerging perception gap is becoming a new strategic challenge—and how leading organizations are measuring, validating and closing it.

Request your seat by completing the registration form.

Why Join the Roundtable

Explore how leading organisations are managing AI-driven reputation risk

Understand how peers are approaching ethical considerations, governance, and oversight as AI increasingly mediates how their organisations are represented.

Get ahead of shifting stakeholder expectations

Discuss how stakeholder engagement strategies are evolving as AI-driven intelligence reshapes how expectations are formed and escalated.

Unpack how AI agents and GEO are influencing perception

Examine how generative answers and AI agents are already shaping how stakeholders see your organisation — often beyond traditional communications channels.

Discuss how to turn AI-driven insights into executive action

Share approaches for translating new forms of reputation and visibility data into clearer priorities, sharper decisions, and more effective leadership responses.

Who’ll attend

This roundtable brings together a small group of senior leaders from Bay Area companies. Attendance is by invitation only and limited to ensure a genuine peer-level conversation.

Chief Communications Officers and heads of corporate affairs

Chief Risk Officers and senior risk leadership

General Counsel and senior legal officers

About the Presenters

Shahar Silbershatz

Shahar Silbershatz - CEO and Co-founder, Caliber

As CEO of Caliber, a Copenhagen-based stakeholder intelligence company, Shahar helps organizations build trust through strategic consulting, stakeholder insights and digital solutions. He holds an MBA from Columbia Business School and has more than 20 years of experience advising some of the world’s largest companies on marketing, communications, business strategy and stakeholder relations.

Mike Sacks (1)

Mike Sacks - Managing Director, MWW

Mike Sacks is a Managing Director at MWW and a trusted crisis advisor to Fortune 500 executives, with nearly two decades guiding organizations through regulatory investigations, cyberattacks, M&A, and reputation-defining moments. He specializes in C-suite advisory, stakeholder engagement, and AI-driven communications analytics—helping enterprises protect value and build trust in high-stakes environments. Mike was named to PRWeek’s “40 Under 40.

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