Cyber Intelligence for the C-suite
Board-Grade Insight at Machine Speed.Digital Squared combines senior executive judgment with AI-native research, analysis, and delivery systems. We help CEOs, boards, and investors turn AI from experimentation into an operational advantage.
"Strategy without execution is a board presentation. Execution without strategy is expensive rework. We do both"
— Tom Andriola, Digital Squared
HOW WE SHOW UP
Pressure-test your AI strategy before the board sees it
Surface where the operating model is leaking value with data, not opinions
Engineer recommendations that survive execution built for your team to actually implement
Stay through the build with retainer partnerships available through delivery
The Gap
Most AI Transformations Stall between the Boardroom and the build Queue
The old consulting model sold information, hours, and large teams to get to an answer. That model is breaking. AI can now accelerate research, analysis, and synthesis faster than any junior team ever could.
What AI cannot replace is judgment. Knowing which questions matter. Knowing what will survive inside a real organization. Knowing how to move from strategy to execution without losing the thread.
Digital Squared was built for that gap. We bring operator experience across healthcare, technology, education, and Fortune 100, then multiply it with co-intelligence: AI systems, curated data, reusable methods, and domain expertise. The result is faster insight, lower overhead, and a direct line between strategy and outcomes.
Data-backed. Board-defensible. Built to compound.
Who We Are
Tom - Executive, Healthcare & Technology
Three decades leading technology and business strategy across healthcare, health & longevity, and Fortune 100.
Arthur - Portfolio Management, Technology & eCommerce
Enterprise technology leader and AI systems architect. $3B+ in platform-driven growth across Gap Inc., DoorDash, Avolta, & Chipotle.
Executive advisory is the front door. We sit alongside leadership to pressure-test strategy, surface where the operating model is leaking value, and engineer the next level of growth — every recommendation backed by a proprietary co-intelligence platform and primary research. When clients want us through execution, we stay on retainer until the outcomes increase sharholder value.
• Sitting-CIO judgment, not retired advisor opinions
• Proprietary co-intelligence platform under every recommendation
• Primary research, not benchmark recycling
• Board-defensible strategy, growth-stage outcomes
• Retainer engagements available through execution
Where We Operate
Industry Fluency. Not Surface-Level Familiarity.
We go deepest in sectors where governance, regulation, and operational complexity make AI adoption harder. The stakes of getting it wrong are highest here.
Healthcare Executive leadership across 6 UC health centers and $16B in system revenue. HIPAA fluency. FDA AI/ML guidance. Clinical decision support. Board roles at OCHIN and Natus Medical.
Higher Education Led IT strategy and shared services across 10 universities at an institutional scale. Research computing. Student data governance. AI workforce development.
Enterprise & Fortune 100 Combined 30+ years of operating experience across global healthcare, retail, e-commerce, travel, and technology. Platform modernization, M&A integration, operating model turnarounds, and $3B+ in measurable portfolio growth.
PE, VC & Regulated Industries AI diligence for investment thesis validation. Governance frameworks for portfolio companies. Board-ready deliverables built for capital allocation decisions.
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