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

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.

The Hidden Costs of Open-Weight AI Every Exec Must Know

expert panel

Open-weight large language models have become one of enterprise AI's hottest topics. Their promise is compelling: greater control, improved privacy, customization and freedom from vendor lock-in. Yet many executives remain focused on one number—the licensing cost—while overlooking the far larger operational commitment required after deployment.Members of the Senior Executive AI Think Tank, a community of executives and practitioners leading AI strategy across industries, agree that organizations should evaluate open-weight models the same way they would any other mission-critical technology platform: through total cost of ownership, long-term operational resilience and measurable business outcomes.McKinsey has emphasized that successful AI adoption depends not only on selecting the right models but also on building the data infrastructure, operating models and organizational capabilities needed to scale them. For enterprises adopting open-weight models, those ongoing investments can quickly become a larger cost factor than the model itself.In this article, AI Think Tank members examine the hidden costs and strategic considerations behind open-weight AI adoption, sharing how executives should think about infrastructure, talent, security, governance, maintenance and the business cases where owning and operating these models can create a meaningful advantage—and when the hidden costs outweigh the benefits.

OpenAI's New Jalapeño Chip: Why Cheap Inference Changes Everything

expert panel

When OpenAI unveiled Jalapeño, its first custom AI inference chip developed with Broadcom, the announcement represented more than a hardware milestone. It highlighted a broader shift in the AI industry: the race to make intelligence faster, more affordable and more accessible at scale. As the cost of running large language models declines, product leaders face a new question—not simply what AI can do, but what products become possible when intelligence is inexpensive enough to operate continuously.For much of the generative AI era, product teams have designed around scarcity. They have limited model usage, shortened context windows, reduced reasoning steps and carefully managed AI interactions because every inference call carries a cost. But as custom silicon and AI infrastructure improvements drive down those constraints, AI can move from an occasional feature users activate to an always-present capability embedded throughout workflows. Research from McKinsey & Company estimates that generative AI could create trillions of dollars in annual economic value, but capturing that opportunity will require organizations to integrate AI into core business processes rather than treat it as a standalone tool.Members of the Senior Executive AI Think Tank believe the next generation of AI products will not simply be faster versions of today’s copilots. Below, they explore how OpenAI’s Jalapeño chip could reshape product design, unlock previously uneconomical AI applications and redefine the competitive landscape for organizations building the next generation of intelligent products.

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