Former B-52 Pilot · Tech Executive · Board Director · Author · Speaker

Bob Wilson.Executive judgment for technology decisions that matter.

Thirty years helping organizations align technology, AI, and business strategy — and make better decisions under uncertainty.

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About

I've spent my career helping organizations make better decisions under uncertainty — in the cockpit, the boardroom, and the CTO's office.

B-52 Aircraft Commander. Section 16 officer at a publicly traded company. Current board director for three non-profits. CTO and managing partner across enterprise technology, cloud, and AI. The common thread isn't a technology stack — it's executive judgment when the answer isn't obvious and the cost of being wrong is real.

Today I work with leadership teams and boards on the calls that are hard to make alone: build or buy, invest or wait, keep the VP or replace them, greenlight the AI project or kill it. Clarity first. Then execution.

How I Help

You're not hiring Kubernetes. You're hiring executive judgment.

Most of what a Fractional CTO or board advisor is really paid for is answering questions like these — clearly, honestly, and without an agenda.

“Should we build this, or buy it?”

“Is this AI project actually worth doing?”

“Should we hire this VP of Engineering?”

“Are we spending too much on infrastructure?”

“Which vendor is bluffing?”

“Is this roadmap realistic — or wishful thinking?”

If those are the questions on your desk right now, that's what a conversation with me looks like. No hype. No jargon. A clear recommendation you can act on.

Capabilities

Three decades of executive judgment — organized around what I can do for you, not where I did it.

Executive Technology Leadership

A seasoned CTO in the room when the stakes are highest.

Fractional and full-time CTO engagements for companies navigating AI adoption, platform strategy, and the tricky in-between years of scale.

AdoptexThe BlueBridge GroupTeam Cloud SolutionsCORE Advanced Technologies

What came of it

Set AI and platform direction for growth-stage and enterprise teams.
Turned around a public technology company as a Section 16 officer.
Built and led global engineering and consulting teams up to 240 people.

Enterprise Transformation

Multi-billion-dollar product portfolios, delivered.

Twenty years shaping cloud, converged infrastructure, and data-center modernization for Fortune 1000 organizations — from technical architecture through go-to-market.

Dell EMC / VCEXiotech (a Seagate company)Solutioneering GlobalCloverleaf Communications

What came of it

Guided VCE from $0 to $2B+ in annual revenue in four years.
Launched VxBlock 1000 — $50M sold in Q1; channel grew to 40% of route-to-market.
Consolidated five data centers into one facility — $3M saved, 99.999% uptime.

Business Growth & Go-to-Market

Turning technology decisions into revenue.

Channel programs, partnerships, and executive selling motions that translate technical capability into predictable, repeatable pipeline.

XiotechCloverleaf CommunicationsDell EMCApple (global reseller)

What came of it

Grew channel revenue 438% in one year — $8M to $43M at Xiotech.
Generated $100M in Fortune 500 pipeline in six months at Cloverleaf.
Closed the first-ever global reseller agreement with Apple Computer.

Judgment Under Pressure

Decision-making forged in the cockpit and the boardroom.

B-52 Aircraft Commander and Instructor Pilot. Section 16 officer of a public company. Current board director for three non-profits. The common thread is clarity when the pressure is on.

United States Air ForcePublic company boardsNon-profit boards

What came of it

Maintained situational awareness and crew discipline on a strategic nuclear platform.
Public-company governance, SEC reporting, and shareholder accountability.
Active governance today for Veterans Count, NH State Veterans Cemetery Association, and Air Force STEM.

Full chronological history — from B-52 Aircraft Commander to CTO — is on the résumé.

Download résumé

Board Qualifications

A "full-stack" board candidate — governance, finance, operations, and strategy.

Governance, Oversight & Fiduciary Responsibility

Current board service for Veterans Count (Easter Seals), New Hampshire State Veterans Cemetery Association, and Air Force STEM / StellarXplorers.
Former Section 16 officer at a publicly traded company with deep understanding of SEC regulations, shareholder value, and public market reporting.
Led a public company turnaround at Tricord Systems, demonstrating resilience and strategic pivot capabilities.

Financial Stewardship & P&L Impact

Drove a 438% increase in channel revenue in a single year at Xiotech.
Built a $100 million pipeline in six months at Cloverleaf.
Increased shareholder value by 2.5X at Western Digital in less than 18 months.
Delivered $3 million in annual savings by consolidating five data centers into a single high-availability facility at CORE ECS.

Operational Excellence & Risk Management

Spearheaded data center transformations that elevated uptime from 98.5% to 99.999%, adhering to rigorous SLAs for government and education sectors.
Military-grade discipline from B-52 Aircraft Commander and Instructor Pilot experience, bringing rigorous risk assessment and crisis management to the boardroom.
Championed Agile Development and follow-the-sun support models to maximize productivity and global operational continuity.

Strategic Innovation & Market Leadership

Led launch of multiple generations of global flagship products (Vblock/VxBlock), guiding a business from $0 to $2 billion in annual revenue.
Deep expertise in AI, Cloud, and IoT, ensuring organizations remain future-ready.
Built global sales channels from the ground up, closing the company's first-ever sales and securing strategic global reseller agreements such as Apple Computer.

Why Bob for the Board?

Bob Wilson is a "Full-Stack" Board Candidate. He offers proven governance experience (via his current non-profit board seats), financial rigor (public company background), and technical vision (CTO/Innovation). He is uniquely positioned to guide organizations through the complexities of the AI revolution while maintaining the operational discipline and ethical standards required of a public servant.

Highlights

Selected projects & outcomes.

Dell EMC · VCE

VCE: $0 → $2B+ in four years

Provided technical leadership and architecture for converged infrastructure that scaled a new company from launch to multi-billion-dollar revenue.

Go-to-Market

VxBlock 1000 launch — $50M in Q1

Led the global go-to-market for the flagship converged systems product; channel partners grew to 40% of route-to-market, generating $1B+ in fiscal-year sales.

Xiotech

438% channel revenue growth in one year

Built a new global channel program at Xiotech in the first 90 days, growing channel revenue from $8M to $43M.

CORE ECS

$3M saved · 99.999% uptime

Consolidated five K-12 data centers into one high-availability facility supporting 11 million students and 1,500 remote developers.

Cloverleaf

Apple global reseller agreement

Closed Cloverleaf's first sale and its global reseller agreement with Apple Computer — and $100M of new pipeline in six months.

Speaker · Mentor

Professional speaking & mentorship

Speaking on leadership, disruption, and the human side of technology; mentoring the next generation of innovators through CyberPatriot and StellarXplorers.

Books

Three books on aviation, companionship, and leadership.

From the cockpit of the B-52 to raising a faithful dog to leading teams under pressure — stories and lessons drawn from a life spent flying, building, and leading.

Book 01

Wings of Endurance

The Venerable B-52 Stratofortress.

An insider's tribute to the B-52 Stratofortress — the people, missions, and engineering that have kept this iconic bomber flying for generations.

Learn more

Book 02

Raising a Faithful Companion

Puppyhood to Lifelong Friend.

A practical, heartfelt guide to raising a confident, well-bonded dog — from the first weeks at home through the rewarding years that follow.

Learn more

Book 03

Adapt. Lead. Succeed.

Leadership Lessons from the Cockpit to the Boardroom.

Hard-won leadership principles drawn from decades flying B-52s and leading technology organizations — how to adapt under pressure, lead with clarity, and build teams that win.

Learn more

Skills