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Boykin Enterprise Transformation Advisory Services

Visionary strategy. Pragmatic execution. Undeniable results.

Pentagon-tested modernization leadership for federal and defense organizations — and hands-on fractional executives for businesses scaling in regulated, mission-critical markets.

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28+
years of defense & enterprise leadership
$500M+
annual IT portfolio led
$1.6B
in capital efficiency unlocked
18,000+
users on analytics platforms scaled
Two practices, one operator

The gap between strategy and execution is where value is lost. We close it.

Whether you lead a federal portfolio or a fast-growing company, the failure mode is the same: vision that never becomes operating reality. Choose your door.

For federal & defense leaders

Federal & Defense Advisory

The “De Facto CIO” at your side — senior advisory for modernizing federal IT portfolios, enforcing fiscal governance, and deploying scalable analytics.

  • Enterprise modernization strategy & portfolio rationalization
  • IT governance, CPIC & FIAR audit remediation
  • Data & analytics transformation (AI/ML, executive dashboards)
  • Strategic facilitation & “frozen middle” breakthroughs

Serving government executives, program offices, and the contractors who support them.

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For CEOs & founders

Fractional Executive Services

A seasoned COO or CIO — without the full-time overhead. Operational discipline for small businesses scaling in regulated, mission-critical markets.

  • Fractional COO: operating cadence, people systems & delivery
  • Fractional CIO: technology strategy, governance & modernization
  • Contract delivery, compliance & audit readiness
  • 30-day diagnostic → 90-day build → ongoing retainer

Serving founder-led GovCon, defense, and regulated commercial companies (20–150 employees).

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Shannon H. Boykin, Founder & Principal
Founder & Principal

Shannon H. Boykin

A senior leader with 28+ years across the defense space, Shannon doesn’t just advise on transformation — he architected it at the highest levels of government. As a Deputy CIO at the Pentagon he held P&L-style accountability for a $500M+ annual technology portfolio of 170+ systems, and today he serves as VP of Operations for a rapidly scaling GovCon small business. He brings the pressure of the chair, and the speed of mission, to every engagement.

M.S., National Security Strategy (National War College) · M.S., Management & Leadership · Active TS/SCI clearance

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Not sure which door is yours?

Start with a 10-minute fit check. You’ll leave with a straight answer about whether — and how — we can help.

Schedule a 10-minute fit check