About
Haywood Wells
Executive technology strategist with deep technical judgment, the leader companies call before an AI or technology decision turns into an expensive mistake
25+
Years Experience
$80M+
Federal Contract Portfolio
13–15
OneMAC Team Led
Candidate
Drucker School Doctorate
Executive Summary
Haywood Wells brings 25+ years of executive strategy and governance leadership across three distinct operating environments: Fortune 100 enterprises, federal government contractors, and high-growth startups. He is the executive companies call before an AI or technology decision turns into an expensive mistake, helping leadership teams move quickly without becoming more fragile in regulated, complex, and scaling contexts.
Haywood is Founder and Principal Executive Advisor of Wells Executive Advisory and a former Chief Technology Officer at Lucky Rabbit LLC. He combines pricing, margin protection, forecasting, and organizational leadership with technical architecture and engineering depth: evaluating designs, guiding engineers, and assessing prototypes. He holds an MBA in Accounting and Finance and is a Doctoral Candidate in Strategy and Governance of Global Innovation at the Drucker School of Management, Claremont Graduate University, with completion expected in 2029.
Career Progression
Wells Executive Advisory
February 2026 – PresentFounder and Principal Executive Advisor
Executive advisory focused on technology strategy, AI adoption, cloud modernization, operating models, governance, and investment decisions for regulated organizations.
Key Achievements
- •Develop executive diagnostics connecting strategic options to cost and risk tradeoffs, decision rights, milestones, and execution plans.
- •Design regulated AI governance and enterprise architecture approaches covering RAG, model evaluation, human oversight, access controls, audit logging, and vendor accountability.
- •Deliver executive briefings, workshop proposals, and advisory frameworks on responsible AI and modernization.
Lucky Rabbit LLC
2021 – 2025Chief Technology Officer
Led technology, operating analysis, growth support, capture, pricing, and executive decision support for a $20M–$30M federal technology-services portfolio supporting CMS and DHS/USCIS modernization.
Key Achievements
- •Built pricing models, margin scenarios, forecasting, and resource-allocation analysis to support investment, hiring, and bid/no-bid decisions.
- •Led technical strategy for the CMS MACPRO recompete, contributing to an approximately $1.5M award for Lucky Rabbit.
- •Built and led a 13–15-person OneMAC organization, with operational influence across a broader 60-person program.
- •Improved release cadence from more than six weeks to two weeks; achieved first-pass penetration and security testing.
- •Proposed and directed a framework migration completed in two months against a four-month timeline while maintaining service availability and delivery cadence.
- •Sponsored and directed AgentVrify development, leading seven people from MVP to working product in ten months on a $10K–$15K budget.
- •Designed the Fractional CTO initiative that Lucky Rabbit implemented. Developed the Abundant evaluation that led to a partnership; leadership accepted a separate venture no-go recommendation.
TechFlow Inc
2013 – 2020Senior Principal Architect
Led modernization advisory across an $80M+ federal contract portfolio serving 15+ civilian and defense agencies.
Key Achievements
- •Aligned technical and executive stakeholders on cloud strategy, security, resilience, investment, cost, and delivery feasibility.
- •Served on the corporate SAFe transformation leadership team, improving planning, alignment, and delivery predictability.
Cardinal Health Pyxis
2005 – 2012Senior New Product Development Engineer / Technical Manager
Managed systems architecture, software/hardware integration, and technical strategy within the Pyxis medication-management ecosystem.
Key Achievements
- •Supported product strategy within a 500+ person organization generating $500M+ in revenue across thousands of clinical environments.
- •Owned product, regulatory, architecture, and technical-diligence workstreams on a four-person executive team evaluating an international dispensing platform for potential IP acquisition.
Navmar Applied Sciences Corporation
2001 – 2005Software Engineering Supervisor
Supervised Marine Corps command-and-control, mission-planning, and defense software delivery with Northrop Grumman.
Education & Credentials
Academic Degrees
Doctoral Candidate, Strategy and Governance of Global Innovation
Drucker School of Management · Claremont Graduate University
Expected 2029
MBA, Accounting and Finance
National University
BS, Electrical and Electronics Engineering
Southern University and A&M College
Executive Education
Executive Certificate, Computer Software Engineering, University of California, San Diego
Research & Thought Leadership
Published White Papers
"Governing Speed: Why Execution Reliability Will Determine the Next Premium in Vertical AI" (2026)
Strategic analysis for boards and executive teams on AI governance and valuation
Published Articles
"Peter Drucker Never Saw an AI Agent. He Already Knew How to Govern One" (2026)
Application of classical management principles to AI governance challenges
Academic Research
Currently completing doctoral dissertation on cross-border governance frameworks enabling execution reliability in complex operating environments. Research integrates 25 years of practitioner experience across Fortune 100, federal contracting, and international expansion.
Speaking & Advisory
Available for board advisory sessions, executive workshops, and conference speaking on governance frameworks, AI deployment in regulated industries, and cross-border execution.
Expertise Areas
Governance & Strategy
- •Decision architecture and governance operating systems
- •Cross-border execution frameworks for international expansion
- •Strategic planning for regulated industries and government contractors
- •Board-level governance for AI deployment and technology transformation
Technology Strategy & Governance Advisory
- •AI governance frameworks for enterprise deployment
- •Technology strategy aligned to governance and business objectives
- •Federal compliance governance (FedRAMP, FISMA, NIST, HIPAA)
- •Investment and risk decisions for technology transformation programs
AI & Technology Risk
- •AI governance frameworks for enterprise deployment
- •Technology investment and risk decisions for boards
- •Vendor, build-vs-buy, and platform modernization strategy
- •Cost control and decision architecture for major technology bets
Federal Contracting
- •Federal procurement strategy and capture management
- •Compliance architecture for federal programs
- •Multi-agency contract execution
- •Government partnership development
Personal Philosophy
"The most expensive failures in complex organizations are not technical failures. They are governance failures. Decisions made too slowly, by the wrong people, without the right evidence, in the wrong sequence.
My work focuses on governance frameworks that make execution reliable: the ability to move quickly, at scale, across complex operating environments, without becoming more fragile. This requires explicit decision architecture, accountability structures, and evidence standards, not lengthy approval processes.
Execution reliability is not an operational detail. It is a strategic capability."
Working on governance challenges in regulated environments, international expansion, or AI deployment?