The Principals
Tom & Arthur
Senior operators. AI-native delivery. One standard of rigor.
Tom Andriola - Principal
Three decades as a technology and business executive across healthcare, higher education, and Fortune 100. Led IT strategy for a 10-university system with $1.4B in annual technology spend and 8,500 staff. Ran a $240M EBITDA business transformation for a global healthcare company. Delivered $346M in documented IT cost savings. Built a healthcare software portfolio from zero to $56M in four years. Appointed to the White House Commission on Cybersecurity and the California AI Commission. Named a Top 30 Healthcare IT Influencer (2025) and Top 50 Higher Ed Voice to Follow (2025). Currently serves as Field CIO at Dynatrace and holds board seats at OCHIN, Natus Medical, UC Davis IIFH, and Engage3.
Arthur Paula - Principal
Enterprise technology leader and AI systems architect. $3B+ in platform-driven growth across Gap Inc., DoorDash, Avolta, Chipotle, and Local Kitchens. Built a net-new e-commerce vertical from zero to $200M at DoorDash across 500+ markets in under 18 months. Led a $260M+ loyalty and customer engagement transformation across 100+ airports in North America at Avolta. Ran $45M in infrastructure modernization programs supporting $1B in digital revenue at Chipotle. PMP-certified. 8,000+ hours building AI infrastructure, multi-agent systems, and production automation over five years. Architect of the Digital Squared cyber intelligence engine.
Whats under the hood
A Cyber Intelligence Engine. Not a Consulting Pyramid.
Most advisory firms sell you senior thinking and junior execution. We built the opposite. A system where the senior thinking is baked into the architecture and the execution runs at machine speed.
Digital Squared runs on a cyber-human intelligence platform: a multi-agent AI research and analysis system that pulls from academic, regulatory, clinical, patent, and market sources in parallel. What takes a traditional firm weeks to scope and staff, our system produces in hours, with citations, not summaries.
The models are interchangeable. We use whatever fits the task, no vendor lock-in. The value is in the orchestration layer, the retrieval architecture, and the compression logic that turns 200 pages of research into a board-ready brief. That part is proprietary.
Every engagement runs on the same infrastructure. Whether we're pressure-testing a go-to-market thesis, mapping regulatory exposure, or building a transformation roadmap, the system and the senior judgment behind it stay consistent.
Research at scale
Parallel retrieval across 15+ academic, regulatory, patent, clinical, and market intelligence sources. Synthesized, citation-graded, delivered in minutes.
Strategic Analysis Pipeline
An eight-stage workflow: research, market analysis, lifecycle mapping, business value modeling, and stress testing. Each stage compresses and feeds the next. The same rigor a top-tier firm delivers in six weeks, running in hours.
Model-agnostic by Design
We use whatever model fits the task. No vendor lock-in. The architecture is the asset, not the model.
From Tom
"I have been the consultant. I have been the operator. I have been the executive buying the consulting. And I have been the person accountable when the strategy had to become real.
What I believe today is simple: AI changes almost everything, but it does not eliminate the need for judgment. It makes judgment more valuable.
The organizations that win will not be the ones with the most pilots, the biggest decks, or the loudest AI announcements. They will be the ones that learn faster, make better decisions, redesign how work gets done, and build trust between people and intelligent systems.
Digital Squared exists to help leaders do that work."
How We Work
Four Principles. One Standard.
We start with outcomes, not technology. We use AI aggressively, but not blindly. We move quickly, but with judgment.
Our work is built around four principles:
Experience. Real operating judgment from leaders who have been accountable for outcomes.
Expertise. Deep knowledge across technology, healthcare, education, data, AI, and transformation.
Curiosity. The willingness to challenge assumptions and test what is now possible.
Creativity. The ability to design new strategies, models, and ways of working.
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