Tripp Sills — Enterprise Architect & AI Application Builder

The story

From the hospital data center to an agent fleet.

Four chapters, one throughline: build the platform, then make it carry more than anyone thought it could.

CH.01 — THE FOUNDATION

Halifax Health

Infrastructure Services Manager for a regional health system — networks, data centers, clinical systems. Where I learned that in healthcare, infrastructure is patient care: when the network drops, the ER feels it.

CH.02 — THE SCALE

Community Health Systems

Principal Enterprise Architect through the Meaningful Use–era drive to electronic health records — leading infrastructure and enterprise architecture across 150+ inpatient and acute-care facilities and 5,600 clinics, on one scalable platform every hospital could leverage, from the network core to the handheld at the bedside.

CH.03 — THE INTELLIGENCE ERA

Cisco — CX Healthcare

Director of Solution Architecture & Delivery for Cisco's healthcare customer-experience organization; previously Service Delivery Leader for Architecture & AI. CCIE, with four Cisco AI certifications — driving AI-era architecture for the country's largest health systems.

CH.04 — THE BUILDER

The portfolio

Then I stopped only advising and started shipping: 20 applications, 200+ production agents, live pilots and first customers — built nights and weekends with an agentic AI toolchain, carrying enterprise discipline into Main Street software.

Mission & vision

Why I build.

// Mission

Close the gap between AI strategy and shipped software.

I build agentic applications where purpose-built agents do the real work, humans keep command at the approval gates, and every number on the screen is derived, verified, and honest. Not decks about what AI could do — software that does it.

// Vision

A Main Street that runs on Fortune-500-caliber intelligence.

The charter captain, the independent repair shop, the family practice — every one of them operating with software that watches their compliance, defends their margin, and works while they sleep. Compliant by construction, transparent in its economics.

Method

How I build.

The same architecture discipline I applied to national hospital platforms, pointed at production AI software.

01 / Agent-first

Agents do the work

Every app ships with a fleet of purpose-built agents — 200+ across the portfolio — doing categorization, reconciliation, compliance watching, and chasing. Humans approve; agents execute.

02 / AI toolchain

Cursor · Codex · Claude Code

My daily build stack is agentic end-to-end: Cursor as the AI-native editor, OpenAI Codex and Claude Code as coding agents — plus MCP integrations and RAG pipelines inside the products themselves.

03 / Every screen

Web to iOS & Android

Production web apps plus native mobile builds — React Native / Expo and Capacitor — so the same platform runs in the browser, on the phone, and in the field. From the network to the handheld, still.

04 / Regulated by design

Compliance as a feature

Florida's Motor Vehicle Repair Act, NOAA SEFHIER / IFQ / USCG rules, livery law, HIPAA posture, FTC franchise disclosure — encoded into the workflows, not bolted on.

05 / Honest numbers

Derived, never retyped

Every displayed figure is computed from a single source of truth. No hand-typed metrics, no invented stats — a rule enforced across all 20 apps and their documentation.

06 / Enterprise spine

Platform discipline

Multi-tenant Postgres with row-level security, generated architecture documentation, schema-validated agent proposals, parity tests, governed phase gates — enterprise architecture, miniaturized.

Twenty-five years architecting enterprise technology. Then I started shipping it myself.