Michael Di Iacovo — Enterprise Architect | Cloud, AI & Federal Systems

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

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 an LLM-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

What I've Built

FROM ARCHITECT TO FOUNDER

CRES

CAREER REBRAND & ENHANCEMENT SUITE

View Live Site →

An AI-powered career platform that connects job seekers with recruiters through intelligent resume optimization, interview preparation, and a two-sided talent marketplace. Built end-to-end — architecture, backend, frontend, AI integration, billing, and deployment.

→ FOR JOB SEEKERS

AI resume optimization with ATS scoring. Mock interviews with real-time feedback. Career coach agent that knows your full profile. Opt-in talent marketplace with privacy controls.

→ FOR RECRUITERS

Semantic candidate search via vector embeddings. Pipeline management with AI copilot. Job board with public careers pages. Smart briefings and automated outreach drafting.

→ THE PLATFORM

Two-sided marketplace where optimized candidates become searchable supply. Each side makes the other more valuable. Stripe billing with subscription management.

React / TypeScript

AWS Lambda

DynamoDB

LLM APIs

Pinecone

Step Functions

Cognito

Stripe

WebSockets

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.

MICHAELDI IACOVO