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

The Real Challenge of Scaling AI Beyond the Pilot

expert panel

The AI industry has been celebrating increasingly capable demonstrations: a model beats a benchmark, an autonomous vehicle completes a route, an AI agent handles a task that once required a person. But a successful demonstration answers only one question: Can the technology work?Commercialization demands much harder answers: Can it work every day? What happens when it fails? Who is responsible? Can the surrounding operation absorb those failures? And do the economics still work when real customers are paying for the result? Nevada’s recent approval of robotaxi networks for Tesla, Waymo and Uber opens the door to thousands of autonomous vehicles operating commercially, and brings those questions into sharp focus.Members of the Senior Executive AI Think Tank bring perspectives from machine learning, enterprise technology, product management, data architecture, financial services, infrastructure, healthcare and design to this next stage of the AI conversation. Below, they examine what it takes to move beyond a working model and build a system that can withstand real-world complexity—from managing failures and infrastructure to earning regulatory and public trust, establishing accountability and making the economics work at scale.

Why AI Data Centers Need a New Infrastructure Strategy

expert panel

The AI industry has embraced a simple idea about data centers: If AI needs more computing power, build bigger facilities and pack them with more chips. But as the infrastructure race accelerates, that assumption is becoming harder to defend. Power availability, grid capacity, cooling, water and the physical limits of getting new facilities online are emerging as constraints that raw compute cannot solve.The question matters because data centers are long-term investments being built around a technology that is changing at remarkable speed. The infrastructure designed for training enormous models may not be what businesses need as inference workloads grow, models become more efficient and AI moves closer to where data and users actually reside.There are also business questions hiding underneath the engineering one: How much compute does a company actually need? Where should it run? What happens when power costs change or a new generation of hardware makes today's architecture less attractive? And how should CEOs think about infrastructure that needs to remain useful even as the AI workloads it supports evolve?Members of the Senior Executive AI Think Tank, a curated group of experts specializing in machine learning, generative AI and enterprise AI applications, offer a range of perspectives on what should come next. In the discussion that follows, they examine whether bigger data centers are really the answer, where power and efficiency fit into the equation, why inference deserves a different infrastructure strategy and which overlooked factors—from memory and networking to reliability and data governance—could determine whether an AI investment delivers lasting business value.

When AI and Experience Clash: Letting Humans Challenge the Machine

expert panel

The machine says the patient is low risk. The veteran clinician says something feels wrong. The AI recommends cutting a workstream. The executive team knows that workstream is critical to a customer they are trying to win. The coding assistant produces perfectly functioning code—except it has quietly recreated a function that already exists somewhere else in the codebase.These aren't hypothetical scenarios. They are the kinds of moments leaders increasingly face as AI moves from experimentation into decisions that affect customers, employees, operations and the bottom line. Automatically trusting the machine ignores context, intuition and accountability. Automatically siding with the human can mean overlooking patterns and possibilities that AI can uncover. So what should happen when an AI system and an experienced human reach different conclusions?Members of the Senior Executive AI Think Tank—a curated community of leaders specializing in machine learning, generative AI and enterprise AI applications—have encountered this tension firsthand across healthcare, manufacturing, software development, enterprise transformation, market intelligence and technology strategy. In the examples that follow, they share what happened when AI and human expertise diverged, how their teams responded and what those moments revealed about the roles each should play in high-stakes decision-making.

How AI Transparency Builds Trust in Data Privacy and Security

expert panel

For many customers, the first question they have about an AI-powered product is no longer “What can it do?” It’s “What happens to my data when I use it?”That question is becoming harder for organizations to answer as AI moves deeper into everyday business processes. A customer using an AI assistant, a patient interacting with a healthcare platform or an employee relying on an AI-powered workflow may not know what systems are operating behind the scenes—but they increasingly want to understand how their information is being handled.Where is the data processed? Who has access to it? Is it being used to improve a model? What control does the customer have if they want to change their preferences? These questions are forcing executives to rethink what transparency means in the AI era. A privacy policy alone is no longer enough. Customers want clear explanations, practical choices and confidence that organizations are applying the same principles internally that they communicate externally.Members of the Senior Executive AI Think Tank—a curated group of experts specializing in machine learning, generative AI and enterprise AI applications—say trust will depend on more than meeting regulatory requirements. From stronger governance processes to clearer communication about data use, these leaders share how organizations can build trust while continuing to innovate.

The Hidden Risks of AI Data Architecture—and How to Avoid Them

expert panel

For executives leading AI transformation, one of the most important decisions is also one of the most difficult: deciding where sensitive data should be processed, stored and governed as artificial intelligence becomes part of the enterprise operating model. The architecture choices organizations make today will shape not only their ability to innovate, but also their ability to protect critical information, meet regulatory expectations and maintain trust.The challenge is that there is no single blueprint for secure AI adoption. Leaders must weigh competing priorities, including the speed and scalability of cloud platforms against the control and data sovereignty of private or hybrid environments, the need for strong governance against the risk of slowing innovation and the benefits of advanced AI capabilities against the responsibility to maintain visibility over how data is used. As AI systems create new layers of information through prompts, outputs, embeddings and logs, organizations must consider not only where data resides, but where it flows and whether they can control its entire lifecycle.Members of the Senior Executive AI Think Tank, a curated group of experts specializing in machine learning, generative AI and enterprise AI applications, examine the most important trade-offs leaders should consider when designing AI architectures for sensitive or regulated data. They also identify common mistakes organizations are making, from focusing only on storage location to overlooking data derivatives, governance gaps and the operational capabilities required to manage AI responsibly. Because architecture decisions are no longer just technical choices—they are business decisions tied to risk, resilience and long-term value.

'We Must Act Now': What Leaders Should Actually Do Today

expert panel

More than 200 economists, AI researchers and technology leaders recently signed the "We Must Act Now" statement, warning that artificial intelligence could reshape the global economy faster than the Industrial Revolution. While the statement calls for stronger institutions and guardrails, it also raises a more immediate question for executives: What should leaders actually do today?Members of the Senior Executive AI Think Tank believe the answer extends well beyond adopting the latest AI tools. Drawing on decades of experience leading enterprise AI, cloud infrastructure, digital transformation and technology strategy, these experts argue that organizations must rethink work itself—redesigning processes, investing in people and establishing governance before AI scales across the enterprise.Their advice comes as organizations accelerate adoption. According to McKinsey's latest State of AI research, AI adoption continues to expand rapidly across industries, with organizations increasingly reporting measurable business impact. Yet the same research also highlights persistent challenges around governance, workforce readiness and risk management, reinforcing the need for thoughtful leadership rather than technology-first decision-making.The following insights from members of the Senior Executive AI Think Tank reveal a consistent message: Organizations that treat AI as a catalyst for better decision-making, stronger employees and more resilient businesses—not simply a cost-cutting exercise—will be best positioned to thrive as AI transforms the economy.

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