Avoid expensive AI and technology mistakes before they reach the boardroom.
I help regulated and scaling organizations make high-stakes AI, technology, modernization, and governance decisions faster without losing control of risk, cost, compliance, or execution.
For CEOs, COOs, CIOs, CTOs, boards, and investors facing AI adoption, platform modernization, compliance pressure, vendor decisions, or diligence risk.
Haywood Wells
Technology and Strategy Executive
Doctoral Candidate · Drucker School
Regulated Technology Leadership
25+ years across federal, healthcare, defense-adjacent, cloud, and enterprise technology environments.
AI Governance & Decision Risk
Experience helping leaders evaluate AI, automation, vendor, platform, and modernization decisions before exposure becomes expensive.
Executive Operating Discipline
Executive judgment across pricing, margin protection, forecasting, organizational leadership, delivery governance, and transformation execution.
Experience Across Regulated and Mission-Critical Environments
Cardinal Health
Fortune 100
CMS
Modernization Programs
USCIS
Federal Contractor
TechFlow
15+ Federal Agencies
Drucker School
Doctoral Candidate
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30-Day AI & Technology Risk Diagnostic
A focused assessment for leadership teams making high-stakes AI, technology, vendor, modernization, or compliance decisions. The diagnostic gives executives an independent, documented view of where the organization is exposed and what to do next.
- Stakeholder interviews and document/system review
- Written findings memo identifying top governance, compliance, security, and execution risks
- Specific recommendation on what to do next, including “no further engagement needed” if that is the honest answer
- Live leadership readout
Investment: $5,000 flat fee, credited toward the first month of an ongoing engagement if signed within 30 days.
Operating Philosophy
“Speed without governance becomes exposure. Governance without execution becomes bureaucracy. The work is building the decision discipline that lets organizations move fast without creating avoidable damage.”
Core Expertise
Strategic Governance at Scale
Governed Execution
Governance frameworks that enable decision velocity, not bureaucracy. Built for Fortune 100, federal contractors, and high-growth companies scaling in regulated environments.
Regulated Modernization
Technology and operating frameworks for organizations modernizing platforms, adopting AI, or scaling in regulated environments. Built for healthcare, GovTech, federal, defense-adjacent, and compliance-heavy organizations where speed, trust, and control must move together.
AI Governance
Strategic frameworks for deploying role-based AI in regulated environments. Published research on execution reliability and governance economics for enterprise AI. Proven across healthcare, government, and financial services.
Deliverables
Proof Pack (sanitized)
Board-ready artifacts that reduce decision latency and improve execution reliability in regulated environments.
Decision Rights Map
RAPID framework + escalation paths, who decides, who inputs, who is informed.
Executive KPI Scorecard
Weekly cadence with named accountability. Variance flags surface before they compound.
Risk Register
Breaking points and mitigations documented. Reviewed on a defined cycle, not reactively.
Evidence Pack Outline
What gets logged, retained, and reviewed, structured for regulatory and board scrutiny.
Example engagement
Regulated mid-market operator · AI & data product launch
Moving quickly into AI- and data-driven products under tight oversight and limited governance. Built a simple, board-visible governance spine, decision rights, risk gates, no-go criteria, and experiment guardrails, so leadership could move faster, launch on time, and stay out of regulatory trouble.
Selected outcomes (sanitized examples)
Regulated modernization program
Decision cycle time shortened from weeks to days by installing RAPID decision rights and a weekly executive scorecard. Program delivery accelerated without adding headcount or expanding scope.
High-volume workflow (federal contract context)
Manual handling reduced significantly by automating intake, instrumentation, and exception review gates. Error rate and rework dropped within the first 90 days of the framework going live.
Why Fractional Executive Leadership?
Strategic Execution Without Full-Time Overhead
Get Fortune 100 governance expertise and federal-scale execution frameworks at a fraction of the cost of a full-time executive.
- Annual cost: $280,000 – $400,000
- Benefits & equity: +$80,000 – $150,000
- Recruiting fees: $80,000 – $120,000
- 12–18 month commitment before results
- Single focus, single company
- Long ramp-up period
- Monthly investment: $10,000 – $30,000
- No benefits, equity, or recruiting fees
- Immediate deployment
- 5–30 hours per week, results-focused
- Brings cross-industry experience
- Expert from day one
Projected Savings
Save $80,000 – $550,000 in Year 1
Assumptions (illustrative)
- •Full-time exec cost includes base salary, bonus, benefits/tax burden, recruiting/onboarding, and separation risk.
- •Fractional comparison covers all three tiers (Advisory through Full Fractional CSO), ranging from 5 to 30 hours per week.
- •Actual results vary by tier, market, and scope.
Immediate Impact: No 6–12 month ramp-up period. Governance frameworks deployed in first 60–90 days.
Proven Expertise: 25+ years across healthcare, defense, enterprise technology, and federal services; modernization advisory across an $80M+ TechFlow portfolio and CTO leadership of a $20M–$30M Lucky Rabbit portfolio.
Flexible Engagement: Scale up or down based on needs. No long-term employment commitment required.
See how fractional leadership can accelerate your growth