Will Conaway's avatarPerson

Will Conaway

PresidentTuxedo Cat Consulting

Charlotte, NC

Skills

Executive Leadership
Growth Strategy and Execution
Information Technology

About

Will Conaway is a distinguished leader with experience across multiple industries in executive roles. He has received the ONCON Icon Award in Global Healthcare and the Constellation's Business Transformation 150 Award. Recognized among Becker's Hospital Review's 100 Hospital and Health System CIOs to Know. Will teaches organizational strategies, leadership, and VUCA concepts, as well as healthcare, at Cornell University. He has a history of service on boards. He is a member of the World Economic Forum and the Forbes Technology Council. He is GenAI certified and has completed the MIT Artificial Intelligence in Health Care program. He is also a Lean Six Sigma Black Belt.

Published content

Where Fortune 500 CEOs Should Make Their First AI Investment

expert panel

Artificial intelligence has become the fastest-moving investment category in the corporate world. Boards are asking about it, investors expect it and competitors are announcing new initiatives seemingly every week. For many Fortune 500 CEOs, however, the challenge isn't deciding whether to invest in AI—it's deciding where to place the first major bet.The stakes are high because the wrong investment can consume millions of dollars while delivering little business value. Organizations across industries are launching AI labs, experimenting with custom models and deploying new tools at scale, yet many still struggle to achieve measurable returns.That reality raises an important question: If you were making your first significant AI investment today, where would you focus—and what would you avoid?To find out, we asked members of the Senior Executive AI Think Tank, a community of leaders and practitioners specializing in machine learning, generative AI and enterprise transformation. Their answers reveal a striking consensus about where AI creates value, why so many organizations get their priorities wrong and the foundational investments that should come before any large-scale AI deployment.

Beyond Prompting: The New Rules of AI Fluency for Leaders

expert panel

For many organizations, AI training has become synonymous with productivity. Employees learn how to write better prompts, automate routine tasks and generate content faster than ever before. But as AI becomes embedded in everyday business decisions, a more important question is emerging: Are organizations teaching people how to use AI, or how to use it responsibly?AI can generate recommendations, summarize information and accelerate workflows, but it cannot assume accountability for outcomes. That responsibility still belongs to people. Yet many training programs spend far more time on tools than on judgment, ethics, governance and critical thinking.This concern is reflected in Deloitte's “The State of Generative AI in the Enterprise” research, which found that regulatory compliance concerns, risk management challenges and the lack of governance models rank among the leading barriers to scaling AI initiatives. As organizations move beyond experimentation, the challenge is no longer simply getting employees to use AI—it is ensuring they can use it responsibly.To explore what modern AI fluency should look like, we turned to members of the Senior Executive AI Think Tank, a curated community of experts in machine learning, generative AI and enterprise transformation. Their perspectives offer a roadmap for moving beyond AI tool proficiency and building the judgment, oversight and responsible-use practices that enable organizations to create lasting value from AI.

Enterprise AI's Next Big Advantage Isn't What You Think

expert panel

Artificial intelligence remains one of the most consequential forces reshaping business, yet many organizations still struggle to distinguish meaningful breakthroughs from attention-grabbing headlines. While public discussion often centers on increasingly powerful models, digital assistants and speculation about artificial general intelligence, many enterprise leaders are discovering that the most transformative AI developments occur behind the scenes.Ask 10 AI experts what will matter most a year from now, and you might expect 10 different answers. Instead, members of the Senior Executive AI Think Tank—a curated group of experts specializing in machine learning, generative AI and enterprise AI applications—arrived at a strikingly similar conclusion: The biggest opportunities—and risks—aren't tied to the next model release. Across industries, they point to the infrastructure that makes AI useful in practice, from governance and security to evaluation, trust and workflow integration. At the same time, many are skeptical of some of today's loudest predictions, particularly around fully autonomous agents replacing human judgment at scale.As recent research from McKinsey suggests, organizations are increasingly finding that AI success depends less on access to cutting-edge models and more on the ability to operationalize them effectively. The experts featured here—those on the front lines of AI innovation—share the developments they believe leaders are underestimating, the trends they think are overhyped and where executives should be investing now to create lasting competitive advantage.

The New AI Arms Race Is About Infrastructure, Not Talent

expert panel

For decades, innovation hubs emerged through a relatively organic mix of academic excellence, entrepreneurial culture, venture capital and geographic density. Silicon Valley became the archetype because talent, capital and ambition concentrated naturally over time. That model is changing. Today, nations and hyperscalers are deliberately constructing AI ecosystems through multibillion-dollar infrastructure investments, workforce initiatives, cloud agreements and regulatory partnerships. Microsoft’s recent multibillion-dollar commitment to expand AI and cloud infrastructure in Australia illustrates how governments and technology companies are increasingly collaborating to shape national AI capacity and digital sovereignty. According to the Stanford AI Index Report, nations are increasingly treating AI infrastructure, semiconductor access and compute capacity as matters of economic and geopolitical strategy. Members of the Senior Executive AI Think Tank say this evolution signals something much larger than a technology boom. It reflects a geopolitical realignment in which compute, chips, data governance and workforce development are becoming instruments of economic and political influence. Here, they explore how engineered AI hubs are reshaping economic power, redefining digital sovereignty and determining which nations and organizations may ultimately control the future AI ecosystem.

The New Collaboration Model in an AI-Driven Workplace

expert panel

The nature of teamwork is undergoing one of the most significant transformations since the rise of the digital workplace. As artificial intelligence moves from a supporting tool to an embedded collaborator, organizations are rethinking not only how work gets done, but what collaboration truly means. A widely cited report from McKinsey highlights that generative AI could automate up to 30 percent of hours worked across the U.S. economy by 2030, fundamentally reshaping roles and workflows. But this shift is not simply about efficiency—it is about redefining the human role within teams. Members of the Senior Executive AI Think Tank—a curated group of leaders specializing in machine learning, generative AI and enterprise applications—believe teams will not necessarily disappear, but will instead evolve into hybrid ecosystems where human judgment, creativity and ethical oversight intersect with AI-driven speed, scale and synthesis. The following insights explore how that evolution will unfold—and what leaders must do to stay ahead.

Key Mindsets Executives Need in an Always-Changing AI World

expert panel

The notion of a “steady state” has quietly disappeared from modern enterprise leadership. In its place is a reality defined by continuous disruption, where artificial intelligence is not just accelerating change but compounding it. Organizations are no longer transforming in phases—they are operating in a constant state of reinvention. For executives, this requires a shift from managing change as an event to leading within change as an environment. Members of the Senior Executive AI Think Tank—a curated group of experts in machine learning, generative AI and enterprise AI applications—bring a front-line perspective to this challenge. Their work across healthcare, cloud architecture, enterprise platforms and AI governance show that the organizations that succeed are not those with the most advanced tools, but those with the most adaptive operating models and leadership mindsets. According to McKinsey’s 2025 report on the state of AI, companies are rapidly scaling AI adoption, yet many struggle to translate that investment into sustained business value—often because their structures, decision-making processes and cultures are not designed for continuous change. To help their fellow leaders better cope with these evolving demands, Think Tank members outline the capabilities executives can no longer treat as optional. Through real-world insights and expert perspectives, they explore how leaders are redesigning operating models, reshaping team expectations and building organizations that don’t just withstand disruption, but continuously learn and perform within it.

Company details

Tuxedo Cat Consulting

Company bio

Our Approach We build future-ready AI programs tightly aligned with organizational strategy that deliver measurable improvements in both clinical and business outcomes. What We Offer Strategic AI Roadmapping We develop comprehensive AI roadmaps tailored to each organization’s unique needs and strategic priorities. Challenge Identification & Prioritization We identify and prioritize high-impact clinical and business challenges that can be effectively addressed through AI solutions. Strategic Alignment We ensure technology initiatives are fully aligned with business objectives to maximize value and return on investment. Capability Assessment We assess current data assets, IT infrastructure, and internal capabilities to support successful AI adoption. Technology Recommendations We recommend AI technologies and solutions with a rigorous focus on ROI and practical implementation. Regulatory & Ethical Guidance We navigate regulatory, compliance, and ethical considerations to ensure the responsible deployment of AI. Implementation Planning We define clear success metrics and implementation timelines to drive accountability and measurable results.

Industry

Information Technology & Services

Area of focus

Hospital
Information Technology
Health Care

Company size

2 - 10