ENTERPRISE ARCHITECT & AI SYSTEMS OPERATOR

MICHAELDI IACOVO

20+ Years // From Pilot to Production

I don't just design architectures — I deploy them into the hardest environments: federal government, financial services, healthcare, regulated cloud. I take complex, high-risk initiatives and turn them into operational systems that deliver measurable outcomes. Not diagrams. Results.

69%
Cost Reduction
10x
Processing Speed
667
Hours Saved Daily
30M+
Docs/Year Processed
TOP 5%
Federal AI Sprint
Hire Me Let's Talk
Engagement Models
HOW I CAN HELP
// Architecture
ARCHITECTURE REVIEW & STRATEGY
Deep-dive assessment of your current architecture, infrastructure, and cloud posture. You get a prioritized roadmap with specific recommendations — not a generic slide deck.
  • Infrastructure & cloud audit
  • Security posture assessment
  • Cost optimization analysis
  • Migration readiness evaluation
// Delivery
PROJECT-BASED ENGAGEMENTS
Hands-on architecture and implementation for defined initiatives. Cloud migrations, AI integration, compliance buildouts, platform modernization — from design through production.
  • Cloud migration & re-architecture
  • AI/ML pipeline design & deployment
  • FedRAMP / compliance buildouts
  • DevSecOps pipeline implementation
// Advisory
FRACTIONAL CTO / ADVISOR
Ongoing strategic guidance without the full-time cost. I embed with your leadership team to guide architectural decisions, vendor evaluations, and technical strategy.
  • Weekly strategy sessions
  • Vendor & tooling evaluations
  • Team mentorship & hiring support
  • Board/investor technical briefings
// Rescue
INCIDENT RESPONSE & TRIAGE
Your production system is down, your migration went sideways, or your audit is in two weeks and you're not ready. I've been the person who gets the call. Short-term, high-intensity engagements.
  • Production incident triage
  • Compliance audit preparation
  • Failed migration recovery
  • Security remediation sprints
Measurable Outcomes
THE NUMBERS DON'T LIE
69%
Cost reduction in federal document processing via AWS-native re-architecture at the U.S. Department of Veterans Affairs
300s→30s
Medical record processing time slashed 10x using AI/ML on AWS — directly improving care delivery speed for Veterans
667h
Hours saved every single day through process automation — 13,000+ hours per month returned to mission-critical work
30M+
Documents processed annually through AI-powered automation pipelines built on serverless cloud infrastructure
30K+
Enterprise users supported with secure backend and identity management systems at the State of Michigan
TOP 5%
Nationally ranked in Federal AI Tech Sprint for GenAI tooling innovation in government healthcare automation
Incident Reports
CASE FILES
01 //
THE $1M DOCUMENT PROCESSING CRISIS
U.S. DEPT. OF VETERANS AFFAIRS
+
⚠ THE PROBLEM
The VA was burning nearly $1M per year processing medical records and documents on legacy infrastructure. Processing times were crippling. Veterans' claims were delayed. Staff was drowning in manual workflows.
◈ SYMPTOMS
300-second average processing time per document. Massive manual review bottlenecks. Compliance reporting was slow and error-prone. Healthcare outcomes were tied to paperwork throughput.
→ WHAT I DID
Designed and deployed AI/ML solutions on AWS — migrating to AWS Textract + Lambda serverless architecture. Built automation pipelines that eliminated manual stages. Re-architected the full processing flow from intake to output.
✓ OUTCOME
Processing time dropped from 300s to 30s. Cost reduced by 69%. 667 hours saved daily (13K+ monthly). Top 5% nationally in AI Tech Sprint for this innovation.
RESULT: ~$690K ANNUAL SAVINGS // 10x SPEED INCREASE // TOP 5% NATIONAL AI INNOVATION RANKING
02 //
FEDRAMP COMPLIANCE OR WE LOSE THE CONTRACT
VETSEZ // FEDERAL
+
⚠ THE PROBLEM
Federal contracts require FedRAMP compliance. The hybrid-cloud architecture wasn't there. Security controls were inconsistent. IAM was fragmented across systems. One audit failure = contract loss.
◈ SYMPTOMS
Identity sprawl across cloud providers. No unified access control framework. Kubernetes clusters without proper security boundaries. Compliance documentation was manual and error-prone.
→ WHAT I DID
Delivered FedRAMP-compliant hybrid-cloud solutions integrating secure identity and access controls. Implemented Kubernetes with proper security posture. Built Zero Trust boundaries across the stack.
✓ OUTCOME
FedRAMP compliance achieved and maintained. Contract secured. Architecture served as the blueprint for future federal deployments across the organization.
RESULT: FEDRAMP AUTHORIZATION ACHIEVED // CONTRACT SECURED // REPEATABLE COMPLIANCE BLUEPRINT ESTABLISHED
03 //
PRISON SYSTEM SECURITY BREACH RISK
STATE OF MICHIGAN // MDOC
+
⚠ THE PROBLEM
Michigan Department of Corrections ran a full penetration test. The results were not good. Critical vulnerabilities in offender-accessible systems. TLS 1.0 still live. Authentication framework was weak and fragmented.
◈ SYMPTOMS
Pen test findings across multiple attack surfaces. Outdated encryption standards across all systems. No unified SSO/SAML framework. Identity perimeter was effectively non-existent.
→ WHAT I DID
Served as Blue Team lead for full remediation. Designed and executed TLS 1.0 deprecation plan across all state systems. Implemented SSO, OAuth, and SAML unified authentication. Hardened all offender-accessible infrastructure.
✓ OUTCOME
All pen test vulnerabilities remediated. TLS 1.0 fully deprecated across 30K+ user environment. Unified authentication framework deployed. State and federal compliance standards met.
RESULT: FULL PEN TEST REMEDIATION // 30K+ USERS SECURED // STATE/FEDERAL COMPLIANCE ACHIEVED
04 //
AI TOOLS THAT SAVED THE SALES CYCLE
STACKHAWK // DEVSECOPS
+
⚠ THE PROBLEM
Sales and Customer Success teams were spending enormous time on repetitive documentation — call summaries, success plans, POV briefs. Deal velocity was suffering. Institutional knowledge lived in people's heads.
◈ SYMPTOMS
Hours lost per week on manual Gong transcript review. Inconsistent MEDDICC capture. POV documents took days. CS success plans were inconsistent and slow to produce.
→ WHAT I DID
Built a GPT-4 powered internal toolsuite: Callsheet (Gong → Salesforce-ready MEDDICC insights), Successplan (auto-generated CS account plans), Solutionbrief (pre-sales POV docs), Stacktrace (AI debug assistant). Also built HawkAuth, which evolved into a customer-facing feature.
✓ OUTCOME
Dramatically reduced documentation burden across Sales, CS, and SA teams. HawkAuth evolved from internal tool to customer-facing product feature. Faster time-to-value for customers. Deal velocity improved.
RESULT: 4 AI TOOLS SHIPPED // INTERNAL TOOL → PRODUCT FEATURE // SALES CYCLE VELOCITY INCREASED
05 //
HARDWARE TURNAROUND: 2 DAYS TO 20 MINUTES
JACKSON COUNTY, MI
+
⚠ THE PROBLEM
Every time a new machine needed to be deployed or reimaged, it took two full days. There was no standard process, no automation, no repeatable workflow. IT was a bottleneck to every department.
◈ SYMPTOMS
Manual, inconsistent hardware provisioning. Staff waiting days for machines. No documented process. Active Directory was disorganized. File share permissions were unaudited and risky.
→ WHAT I DID
Built a standardized, automated provisioning process. Restructured Active Directory and GPOs. Audited and remediated file permissions and licensing. Virtualized all physical servers. Elevated all processes to current industry standards.
✓ OUTCOME
Hardware turnaround time dropped from 2 days to 20 minutes. Clean, secure, repeatable process. Infrastructure fully virtualized. Organization running at current industry standards.
RESULT: 144x FASTER PROVISIONING // FULL INFRASTRUCTURE VIRTUALIZATION // ZERO-DRIFT PROCESS ESTABLISHED
Pattern Recognition
ANTIPATTERNS I'VE SOLVED
💀
LIFT & SHIFT DELUSION
// THE TRAP: "We just move it to cloud"
THE FIX Moving legacy workloads to cloud without re-architecting doesn't reduce costs — it increases them. I've seen 3x bill increases from "migrations" that were just EC2 wrappers around on-prem thinking. The cloud rewards cloud-native patterns. Anything else is renting a sports car to drive 15mph.
🔥
COMPLIANCE AS AN AFTERTHOUGHT
// THE TRAP: "We'll add security later"
THE FIX In federal and regulated environments, retrofitting compliance into a deployed system costs 5–10x more than building it in from day one. FedRAMP, Zero Trust, TLS standards — these need to be architecture decisions, not sprint tickets. I design compliance in, not on.
⚡
MONOLITH DISGUISED AS MICROSERVICES
// THE TRAP: Same deployment, smaller containers
THE FIX Kubernetes doesn't fix a bad architecture — it scales it. I've walked into orgs where every "microservice" shared the same database, deployed in lockstep, and failed together. That's a distributed monolith. Real decomposition requires domain boundaries first, containers second.
🧱
MANUAL EVERYTHING IN CI/CD
// THE TRAP: "The pipeline runs, someone approves"
THE FIX Manual gates in a CI/CD pipeline are a false sense of control. If a human has to click "approve" on every deploy, you don't have continuous delivery — you have scheduled deployments with extra steps. I build pipelines with automated quality gates, security scanning, and real rollback strategies.
👻
OBSERVABILITY THEATER
// THE TRAP: Dashboards nobody reads
THE FIX Having Datadog doesn't mean you have observability. Alerts that fire 200 times a day train teams to ignore them. Dashboards with 40 panels that nobody opens are decoration. Real observability means the right signal, to the right person, at the right time — with actionable runbooks attached.
🤖
AI PROOF-OF-CONCEPT PURGATORY
// THE TRAP: Endless pilots that never ship
THE FIX Most orgs have 5 AI POCs and 0 production AI systems. The gap isn't the model — it's the integration layer, the data pipeline, the security review, the change management. I specialize in getting AI from pilot to production: architecting the plumbing that makes demos into deployments.
The Toolkit
THE STACK
AWS
Azure
GCP
Kubernetes
Terraform
Docker
Python
Bash / PowerShell
LLMs (GPT, Claude, Gemini)
Pinecone / Vector DBs
RAG Architecture
Prompt Engineering
REST APIs
OAuth2 / JWT
GitHub Actions
Jenkins
Datadog
AWS Textract
Lambda / Serverless
FedRAMP
Zero Trust
TLS / IAM
SAML / SSO
Helm
Ansible
API Gateways
EKS / AKS
DevSecOps
SAFe 5
Pre-Sales / PoC
Executive Advisory
Working Together
HOW IT WORKS
DISCOVERY CALL
Free 30-minute conversation. You tell me what's broken, what's urgent, and what success looks like. I tell you honestly whether I can help — and if I can't, I'll point you to someone who can.
ASSESSMENT
I dig into your environment, architecture, and constraints. This isn't a checklist — it's a hands-on investigation. You get a clear picture of where you are and what needs to happen.
EXECUTION
We agree on scope, timeline, and deliverables. I work embedded with your team — not in a silo. Regular check-ins, working code, and measurable progress. No vanishing-consultant syndrome.
HANDOFF
Everything I build, your team can maintain. Documentation, knowledge transfer, and runbooks are part of every engagement. I'm successful when you don't need me anymore.
Social Proof
DON'T TAKE MY WORD FOR IT

I let my work and the people I've worked with speak for themselves. Check out recommendations from colleagues, clients, and leadership on LinkedIn.

View Recommendations on LinkedIn
Organizations I've Worked With
Let's Work Together
READY TO BUILD SOMETHING GREAT?

20+ years. Federal systems. Financial infrastructure. AI in production. If you need someone who can take your hardest problem from whiteboard to working system — let's talk.

Book a Discovery Call Send an Email
EMAIL
Diiacovo@gmail.com
LINKEDIN
linkedin.com/in/michaeladiiacovo
LOCATION
Michigan — Remote (ET preferred)
CLEARANCE
Tier 4 Public Trust (Active) · U.S. Citizen