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Authenticity and AI: Navigating the Trust Gap

PRIVATE EXECUTIVE DINNER – SAN FRANCISCO – JUNE 17, 2026

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On June 17h, 2026, Caliber and Okta hosted a private dinner bringing together senior leaders for an open, peer-level discussion on how AI is reshaping corporate reputation and what it takes to protect it.

AI is changing how companies operate, communicate, and make strategic decisions. But at what risk to corporate reputation? To stakeholder trust? To the credibility and authenticity that leaders have spent years building?

The dinner brought together senior executives for a candid, confidential, peer-level conversation on some of the defining challenges of the moment, grounded in real data and live organisational challenges.

Download our snapshot on Public Perceptions of AI and Its Leading Companies, to explore the data we discussed on the night.

KEY TAKEAWAYS

01

AI adoption is top-down — and creating friction. Across organizations, AI is a C-suite and board-level priority. But where adoption is being forced rather than encouraged, it’s generating internal pressure, distrust, and tough conversations between leaders and their teams.

02

Optimism about potential, frustration with reality. There was broad agreement that Corporate America is in a messy transition phase — leaders are bullish on where AI is heading, but underwhelmed by current tools and use cases.

03

A widening sophistication gap. Some organizations are building and deploying agents at scale; others are still using AI as a glorified search bar. Regardless of maturity level, a near-universal anxiety persists: are we moving fast enough?

04

The human touch still matters — for now. Communicators worry AI will erode the creative work that drew them to the profession. But the room largely agreed that authenticity and stakeholder trust still require a human hand, at least in AI’s current state.

05

Employees are pushing back. Beyond the fear of being replaced, employees are raising concerns about privacy, environmental impact, and algorithmic bias — concerns that leaders are increasingly having to navigate and respond to publicly.

06

Regulation is lagging, and trust is the casualty. AI tools remain largely unregulated and opaque. With little faith in regulators to close the gap, the burden of building trust falls on AI developers themselves — and those who deploy their tools.

Who’ll attend

This dinner 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

We discussed:

  • The risks of using AI in industries where trust is the product: where does it help, and where does it actively undermine you?
  • The authenticity gap: what happens to perceived credibility when AI reduces the role of human judgment in how a company communicates?
  • What Caliber data reveals about public trust in AI — and in the companies behind it
  • How Okta works with building trust — through both its product offering and its stakeholder relationships.
  • How real-time stakeholder intelligence helps leadership teams make smarter decisions — and the role of AI in surfacing the signals that matter
Join the discussion

About the Organizers​

Caliber is a global stakeholder intelligence platform that helps organisations understand and manage the perceptions of the people who shape their success. With over four million stakeholder interviews conducted across 60+ countries, Caliber supports senior leaders in connecting communications, reputation, and engagement to measurable outcomes.

Okta is an identity and access management platform that helps organisations control and secure how people and systems connect to technology. Its tools cover everything from single sign-on and multi-factor authentication to access governance — making it easier for large enterprises to manage who can access what, across applications, devices, and teams.