In 2025, Executive Connections formally launched its AI Practice to help boards and CEOs navigate one of the most consequential—and most misunderstood—technology shifts of our time. As preparation for launching our new AI practice, EC identified and complied a confidential database of 50+ Chief AI Officers candidates which has enabled our firm to hit the ground running.
The decision to launch was driven by clear patterns we were seeing across the market and across our client work.
Discerning Depth From Surface-Level Fluency in AI Leadership
First, we encountered an unprecedented level of AI skill attribution. As interest in artificial intelligence accelerated, the market was quickly flooded with newly minted “AI experts” – many fluent in current terminology, frameworks, and tools, but far fewer with meaningful experience building and scaling AI in complex organizations. As we spent 6+ months building a roster of top AI talent we frequently heard polished, confident language:
- “We’ll leverage generative AI to unlock enterprise productivity”
- “Our approach is use-case driven and model-agnostic”
- “We’re deploying AI copilots across the organization”
- “Responsible AI is embedded in our strategy”
In contrast, top AI executives who had spent a decade or more driving innovation using machine learning and applied AI spoke very differently. Their focus was less on slogans and more on specifics:
- How data quality and availability constrained model performance
- Why promising pilots failed when moved into enterprise-wide rollout
- Where organizational design, incentives, and governance slowed progress
- How they balanced experimentation, cost, risk, and measurable return
- Lessons learned from deploying models into messy, real-world systems
Our clients consistently tell us that what they value most about Executive Connections is our ability to quickly understand their needs and culture, and to discern candidate depth from surface-level fluency. As AI language became widespread almost overnight, boards and CEOs needed help evaluating whether an executive’s expertise was shaped by real-world execution or recent exposure to emerging tools. We saw a clear need to bring clarity and judgment to a rapidly evolving leadership market.
A Familiar Pattern: From Internal Efforts to Proven Leadership
Second, AI adoption began to follow a familiar pattern.
In earlier waves of digital transformation (most notably e-commerce) companies initially relied on internal leaders to advance new initiatives. While capable and committed, many lacked experience navigating enterprise-wide change. Over time, boards and CEOs grew frustrated with uneven progress and unclear business impact.
AI is unfolding in much the same way.
Many organizations began with pilots, innovation labs, and centers of excellence. Early experimentation delivered promise, but results were inconsistent. As expectations rose, leadership teams increasingly recognized the need for executives who had already led AI transformations—leaders who understand not just algorithms, but operating models, data infrastructure, organizational change, and accountability for results.
In 2026 the market now appears to be bearing this out.
Why Executive Connections?
Launching an AI Practice was a natural extension of how Executive Connections has always partnered with clients. EC was ahead of the curve when marketing shifted to a digital- and mobile-first axis, and we helped clients shift CMO profiles to include significant data analytics and digital transformation skills and experience. Our firm also hired some of the first Chief Digital Officers when this position was added to Executive Leadership teams. Similarly, EC is leading clients in creating and staffing senior-level AI executive roles.
Our work has never been about chasing trends or filling roles defined by buzzwords. Clients describe us as trusted advisors who bring perspective, rigor, and access to leaders with proven execution experience. That approach is especially critical in AI, where mis-hires are costly and false confidence can delay progress by years.
The Executive Connections AI Practice is designed to help organizations:
- Identify AI and machine learning leaders with demonstrated, enterprise-scale experience
- Get past surface-level fluency to understand true depth and capability
- Build leadership teams capable of moving AI from experimentation to sustained business impact
As AI transitions from promise to performance, leadership – not technology – will determine success. Executive Connections is proud to help our clients get that leadership right.
Author, Chris Hendren – Managing Director, Executive Connections LLC
Chris Hendren joined Executive Connections seven years ago after retiring early from IBM, where he spent decades operating at the intersection of advanced analytics, technology, DTC, and business transformation.
At IBM, Chris served as VP General Manager for Analytic Solutions within IBM’s newly formed Analytics business unit. In this role, he was responsible for the definition, design, delivery, and commercialization of industry-specific analytic solutions.
Under his leadership, IBM launched two major analytic solutions, delivering descriptive, predictive, and prescriptive analytics directly into the hands of merchants, product managers, planners, and marketers. These solutions, combined unstructured data with traditional structured data sources to provide actionable insight into the “why” behind performance.
Chris brings first-hand experience building analytics and AI capabilities inside a global enterprise- that informs Executive Connections’ approach to identifying leaders who can move AI from concept to real business impact.
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