TrippAI — Tripp Sills · Agentic AI Applications & Enablement

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, but 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.

Where it's headed: every application converging on a single data repository, one governed source of truth per business, architected for bi-directional communication in the future, so data flows both ways between the platform, its agents, and every system it serves.

How an engagement runs — the VALUE chain

V — VisualizeSit down in your business. Map the value chain and baseline how work actually flows today.

A — AutomatePurpose-built agents take over the routine execution: the chasing, categorizing, reconciling, watching.

L — Loop in humansPeople stay in command at the approval gates. Judgment calls stay yours; the busywork does not.

U — UnifyConsolidate the tools you barely use into one platform with one source of truth.

E — EvolveEvery 30 days, the next feature your team asked for goes live. The system grows with the business.

Enterprise architecture and AI governance.

AI you can hand real work to is an architecture problem before it is a model problem. Every application here is built inside a governance frame, the same one I would stand up for a hospital system or a defense network, scaled to fit an owner-led business.

Architecture before codeEvery application starts as a system of systems: data model, integrations, and workflows mapped first, with the same enterprise architecture discipline I applied across 150+ hospitals and classified DoD networks.

Humans in commandAgents propose, people approve. Consequential actions route through approval gates with a human on them, so autonomy never outruns accountability.

Standards-alignedThe governance model draws on NIST AI RMF and ISO/IEC 42001: defined agent roles, schema-validated agent proposals, and phase gates between what an agent suggests and what the system commits.

Auditable by designAgent work is visible and reviewable, every displayed figure is derived from one source of truth, and architecture documentation is generated from the system itself, never drawn by hand.

Data kept governedMulti-tenant isolation with row-level security, one governed source of truth per business, and the regulations of each industry encoded into the workflow itself.

The story

From the hospital data center to an agent fleet.

Five 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 at Halifax Health, responsible for the entire technology stack: low voltage, data center build-out, and the application workflows behind bedside medication reconciliation. I architected the technology for a 1.5 million square foot patient tower covering inpatient units and the emergency department, the largest in Florida at over 100,000 square feet. The wireless infrastructure initiative behind it won a 2009 InfoWorld 100 Award, listed with me as project lead. This is where I learned that in healthcare, infrastructure is patient care: when the network drops, the ER feels it.

Low VoltageData Center Build-OutWireless InfrastructureClinical SystemsMedication ReconciliationEmergency Department

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. One scalable platform every hospital could leverage, from the network core to the handheld at the bedside. In the same period I stood up the enterprise architecture practice for a large healthcare provider in the Atlanta area, a team that outlasted the engagement and ran for more than a decade.

Application ArchitectureClinical WorkflowsStakeholder OrchestrationOperational ValuePopulation HealthEHR Adoption

CH.03 — THE HIGH SIDE

Special Operations & DoD

Chief Architect for classified high-side systems supporting Special Operations Forces and the Department of Defense, working out of the Special Warfare Technical Integration Support Center. I briefed general officers on recommended courses of action, grounded in technical research and stakeholder input, covering the personal-area networking and communications that special operations personnel depend on before, during and after an operation. Enterprise architecture and cybersecurity for networks built to a standard where availability is a mission requirement rather than a service level.

Classified SystemsHigh-Side NetworksPersonal Area NetworksCombat CommunicationsCourses of ActionCybersecurity Architecture

CH.04 — 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. I built the healthcare consulting and services practice, serving more than 200 provider organizations with the large majority returning for further work after delivery. We stood up a business development team to evangelize the advisory offerings, but retention came from the delivery itself: AI assessments and healthcare technology strategies built around real operational workflow requirements. Also Lead Architect supporting Cisco's largest as-a-Service customer, a national retailer. CCIE, with four Cisco AI certifications.

Consulting PracticeAI AssessmentsSolution ArchitectureService DeliveryClient RetentionCCIE

CH.05 — THE BUILDER

The portfolio

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

Agentic AIMulti-Tenant SaaSRegulatory EncodingAI GovernanceMobile BuildsLive Pilots

Method

How I build.

The same discipline I brought to hospital systems, Special Operations classified networks with the DoD, and hundreds of technology organizations across the globe: rigorous enterprise architecture, and solid cybersecurity architecture and compliance. Now 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, with deep tool integrations inside the products themselves.

03 / Every screen

Web to iOS & Android

Production web apps plus native mobile builds in 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, all encoded into the workflows rather than 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 and AI governance, miniaturized.

What colleagues say

117 written recommendations.

Written on LinkedIn by the people who managed me, reported to me, bought from me and sat across the table. A selection below, then what they keep saying.

From leaders

“Tripp has a deep understanding of the healthcare market and a unique ability to translate complex technology into practical business value… Tripp has been one of my go-to resources at Cisco because of his reliability, expertise, and ability to connect technology solutions to real-world outcomes.”

Shawn Jean · Author and AI patent holder · 2026

“Tripp was instrumental in building the business case for Community Health System to take advantage of utilizing the Pharmacy OneSource data center… I would highly recommend hiring Tripp for an enterprise architecture position.”

Tim Gibbons · CEO, Pharmacy OneSource

“I found him to be very detail oriented and willing to discuss alternatives that challenged the status quo… I would recommend him without hesitation!”

Randy K Blue · CIO · CIO of the Year, Nashville Technology Council

“Tripp is a highly skilled IT engineer/architect. His input was invaluable to me in multiple projects… He is a very effective communicator, and can easily ‘translate’ business needs to technical or application staff.”

Jim Mayercik · former Vice President, IT

“Tripp is bright, very knowledgeable, and a creative problem solver with a positive outlook and attitude. We regularly turned to him for help when others were unable…”

Sharon Stewart, FACHE, MSHCAD · healthcare IT executive

From architects and engineers

“Tripp is one of the best Enterprise Architects that I have seen. Tripp has a deep knowledge base of not only Systems, but Cisco and Citrix. He has the ability to understand any technical knowledge and apply it to an enterprise mold.”

Joseph Platt · Automation, Virtualization and Cloud Architect

“He has the ability to analyze large complex environments and create effective, efficient technology infrastructures to provide physicians a way to effectively practice healthcare.”

Roy Crookshanks · Senior Regional IT Director

“Tripp has a great talent for balancing the long term technical strategy of a large company and the operational flexibility necessary to implement like a smaller company. He is also adept at being able to speak technical to one group, and business to another.”

Joe Feyereisen · recognized top 2% international project managers

“Tripp played a key role in the design and architecture of the Common Technology Platform… His design approach was based on recognizing and understanding how users would want to interact with technologies.”

Michael Colson · Senior Solutions Engineer, Splunk

“In our discussions, he was always looking for solutions to technical challenges that were balanced against the acceptable levels of business risk.”

Kaj Pedersen · Chartered Fellow, British Computer Society

What they keep saying

Technology into business outcomesUnderstands the business problem first, then builds the technical answer to it.

Large, complex environmentsAnalyzes sprawling estates and produces infrastructure that is simpler than what it replaced.

The one they escalate toThe go-to when others could not produce a practical solution.

Fluent in both registersSpeaks technical to one group and business to another without losing either.

Recommended without hesitationThe phrase recurs verbatim across a decade and a half of reviewers.

Also from Randy Charlick, Steve Hamilton, Karen Woodruff, Marion Stipe, David Wright (Cerner), Michael Walther, Cindy Powell, Michael Ricardo, Wayne Guidry, Rod Gamble, Angelo Hughes, Jeff Darden, Pramod Mathews, Michael Brinkman (Slalom), Sammy Cantrell, Salil Shibad, David Foster, Steve Tarbuck, Preston Davis, Michael Jonas (Microsoft), Chris Wagner, Sherry Helmbrecht, Mike Frendt, Leslie Gove, Jason Whiteaker, Andre Lopes, Bob Marinaro (Datavant), Preston Duren, Tavy Cain, Rich Rairigh, Jody McGinnis, Donald Blevins, Norman Maxwell, Jane Whitesides, David Yoerger, Ken Fuchs, Wade Todd (Cisco), Todd Hargis, Anne Killough, Neal Sivley, Bill Masten, Phil Marchese, Ellroy Dale, David Rippel, Richard McTague (AT&T), Perry Williams, David Poston, Jon Hilfiger, Mac McMillan and many more.

Read all 117 on LinkedIn →

I listen to your business. Then I build real software you can use now.

The Agentic-Native Application Portfolio.