HW
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HW
Haywood Wells
Schedule Consultation

Services

Executive Technology Strategy & Governance

I help regulated and scaling organizations make high-stakes AI, technology, modernization, and governance decisions faster without creating expensive risk, compliance, cost, or execution problems. You get senior executive judgment and federal-scale delivery experience without adding a full-time executive role.

Not sure where to start? Begin with a free consultation. If there is a fit, the $5,000 Full Diagnostic gives you an independent read on your risk exposure and a specific tier recommendation before any retainer commitment.

All Engagements Include

Immediate Access

Start within 1–2 weeks of agreement

Flexible Communication

Slack, email, video, on-site as needed

Results Orientation

Clear deliverables and success metrics

No Long-Term Lock-In

Month-to-month after minimum commitment

Expert Network

Access to specialized resources when needed

Service 1

CTO-Level Technology Strategy & Governance


Who This Is For

  • •CEOs, COOs, CIOs, boards, and investors weighing high-stakes technology decisions
  • •Leadership teams that need CTO-level strategy without adding a full-time CTO
  • •Regulated or scaling organizations that should not pull in a hands-on engineering contractor for strategic calls

What You Get

Executive technology judgment for organizations making high-stakes AI, cloud, platform, vendor, modernization, or compliance decisions. This service helps leadership clarify what to build, what to buy, what to govern, what to stop, and where technical risk could become business exposure.

Deliverables

  • Clear technology decision roadmap
  • Build-versus-buy guidance
  • AI/cloud/platform risk assessment
  • Vendor and architecture decision support
  • Governance and decision-rights recommendations
  • Executive-ready technology risk narrative
Service 2

Fractional CSO: Strategic Execution & Governance


Who This Is For

  • •Organizations scaling operations faster than governance and compliance can absorb
  • •Companies preparing for audit, funding, or acquisition requiring executive-grade governance
  • •Leadership teams needing board-level strategic planning and decision architecture

What You Get

Strategic Planning

  • •3-year strategic roadmap with market opportunities
  • •Governance models for regulated growth, AI adoption, and platform modernization
  • •Technology and operating strategy for regulated growth and transformation
  • •Competitive positioning frameworks

Execution & Support

  • •Decision architecture optimization
  • •Board presentation development and delivery
  • •Strategic partnership identification and structuring
  • •Compliance, stakeholder, and execution-risk planning for high-stakes initiatives

Deliverables

  • Strategic plan with measurable objectives
  • Transformation governance and executive decision-rights framework
  • Monthly strategy reviews with executive team
  • Quarterly board reporting materials
Best Value
Service 3

Full Fractional CSO: Embedded Executive Leadership


Who This Is For

  • •Organizations requiring a full embedded CSO without a permanent hire
  • •Companies scaling AI, technology, or modernization initiatives with board-level governance needs
  • •Organizations deploying transformational AI or digital initiatives at scale

What You Get

  • Everything in Advisory and Strategic Execution services above
  • Full fractional Chief Strategy Officer role
  • Board-level representation and reporting
  • Transformation leadership, executive governance, and decision-risk management
  • Cross-functional executive team integration
  • On-site presence as needed (travel coordinated in advance)
  • Investor and board relations support
  • Crisis governance and rapid decision support

Deliverables

  • All Advisory + Strategic Execution deliverables
  • Embedded CSO leadership with board representation
  • Transformation governance and executive decision-rights framework
  • Monthly joint executive reporting and quarterly board materials

Not sure which engagement fits?

Let's discuss your specific situation and find the right approach for your organization.