Principal-Led Strategic Advisory

Some expertise can't be hired from outside. Ours was built from within.

We have decades inside the current. Now we help you find the channel.

Cloudbreak Advisory Group provides senior-level strategic guidance for organizations managing complex IT portfolios, technology transitions, and high-stakes governance decisions. Our practice is led by David Cheyne — a principal consultant with decades of experience inside Bank of America's enterprise technology ecosystem.

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Southern California • Nationwide Client Advisory
Decades of Enterprise IT Experience
Seasoned judgment tested at global banking scale
Bank of America Portfolio
Personal Compute & Print Services leadership
Managed Budget >$200MM
Direct annual oversight of mission-critical capital programs
Principal-Led Engagements
Direct senior counsel in the room, every single time
David Cheyne - Principal Consultant
>$200MM
Managed annual technology budget inside Bank of America
About Snapshot

Built From Within the Current

David spent his career at the intersection of technology strategy, print services, and digital transformation at one of the world's largest financial institutions.

He's navigated the decisions that don't have easy answers: aging infrastructure, competing priorities, institutional knowledge walking out the door, and portfolios that have outgrown the frameworks built to manage them.

Cloudbreak Advisory Group exists for organizations that need that kind of experience in the room — not a generalist, not a staffing solution, but a senior advisor who has done the work at scale and knows where things go wrong.

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Core Capabilities

What We Offer

Senior-level strategic guidance designed for organizations managing complex IT portfolios, technology transitions, and high-stakes governance decisions.

Independent evaluation of technology roadmaps, portfolio alignment, and multi-year investment health to ensure strategy translates into operational execution.

Establishing clear decision frameworks that de-risk major technical investments, clarify stakeholder accountability, and prepare leadership for board reviews.

Specialized counsel on personal compute and print services transitions, hardware refresh roadmaps, legacy phase-outs, and vendor contract optimizations.

Protecting institutional wisdom before key departures occur and elevating rising technical leaders into confident executive operators.

Direct intervention when critical initiatives stall, vendor relationships deteriorate, or unforeseen architectural roadblocks threaten deadlines.

Facing a decision that needs senior judgment?

We work directly with executive sponsors and leadership teams.

See How We Work
We have worked with :
Bank of America
Apple
Dell
HP
Qualcomm
Samsung
Xerox
Bank of America
Apple
Dell
HP
Qualcomm
Samsung
Xerox
Engagement Models

How We Work

Flexible, high-trust structures tailored to the scale of your challenge.

Advisory Retainer

Strategic Executive Retainer

Ongoing advisory providing executive leadership and IT directors with an experienced sounding board for high-stakes decisions.

  • Regular executive strategy sessions
  • On-call decision review & governance
Targeted Diagnostic

Portfolio & Fleet Health Check

A focused 4-to-6 week deep dive into an active transition, print/compute lifecycle review, or complex vendor contract.

  • Operational & contract audit
  • Clear risk matrix & remediation roadmap
Intervention

Escalation & Turnaround Lead

Hands-on senior intervention when a critical initiative is falling behind schedule, exceeding budget, or encountering vendor friction.

  • Vendor alignment & milestone reset
  • Recovery leadership & risk mitigation
Get in Touch

We work with a select number of clients at a time.

If you're facing a decision that needs senior judgment, let's talk.

Location Base
Southern California • Nationwide Client Advisory
Executive Network
LinkedIn Profile →
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Share a brief note about the decision or transition you are evaluating.

Principal-led reply within 24 business hours. Confidentiality guaranteed.

Thank You

Your note has been sent directly to David Cheyne. He will follow up promptly.