Signal
Build Log // File 001

Andrew
DiCosmo

Open to the Right Opportunity
Andrew DiCosmo
SUBJECT:   Technology Leader & Hands-On Builder
FOCUS:     CTO leadership · AI · Cloud · Security · Applied Technology Platforms
CLEARANCE: TS/SCI w/ CI Poly
LOCATION:  Greater Chicago Area · Northwest Indiana
KNOWN FOR: setting technology strategy and staying close enough to the code to own the outcome
Available Engaged
W-2 or C2C · Flexible start date
PASS 2026.07 · COLLECTION ACTIVECV MODEL · STANDBY
VIEW
BASE STRUCTURES · 97.4% VEHICLE · 96.2% NEW CONSTRUCTION · 93.1% CLOUD COVER · 18% VEHICLE · 41% LOW CONF AIRCRAFT · 98.8% 41°37'12.4"N 87°05'24.0"W SENSOR OPTICAL · EO SUN EL 42.5° GSD 0.3 M/PX 2026-07-07T21:09:15Z
Project stack: PyTorch · TensorFlow · object, change & new construction detection · NGA / IARPA mission areas
HOW I LEAD · OWN THE STRATEGY, NOT JUST THE TICKET

Technology Leadership

I have set technology vision and owned delivery as the senior-most technology leader on the engagement, then stayed hands-on where it mattered. I lead the same way I build: from the decision down to the running system.

LEAD-01

Vision & Strategy

I have owned technology strategy and architecture direction for federal mission programs, including build-versus-buy decisions, vendor selection, secure-cloud standards, and technology roadmaps.

LEAD-02

Build & Lead Teams

I have led engineering and delivery teams, setting architecture standards, code-review practices, hiring standards, mentoring, and career paths while staying accountable for the systems they shipped.

LEAD-03

Practice & Portfolio

As a cloud practice leader, I ran multiple client portfolios from the first whiteboard through delivery, including budgets, estimates, roadmaps, vendor decisions, and executive presentations.

LEAD-04

Governance & Risk

I establish security, compliance, and technology governance using NIST, Azure Security Benchmark, Policy as Code, SOC 2-aligned practices, and AI governance. I have also owned enterprise AI platform planning across Azure AI Foundry, Claude Enterprise, and ChatGPT Enterprise, including approved-model standards, developer access, token management, and cost controls.

HOW I WORK TODAY · CLOSE ENOUGH TO THE CODE TO OWN THE OUTCOME

Hands-On Engineering

I work best where architecture has to turn into running software: production systems, applied AI, cloud services, APIs, data movement, and the troubleshooting that happens after launch.

PROOF-01

Build & Ship

My current work includes Python services, REST APIs, cloud services, data flows, AI integration, and production troubleshooting. I work across the decisions and the implementation needed to make a system dependable.

PROOF-02

Design for Fit

I do not force an agent framework into every AI problem. Some products need deterministic recognition, OCR, pricing, and data-processing flows where bounded services and clear tool calls are the stronger production choice.

PROOF-03

Deliver at Scale

I have led teams modernizing mission systems into API-backed cloud services, including high-volume data platforms with structured and unstructured ingest, computer-vision workflows, and enterprise deployment constraints.

PROOF-04

Client Delivery

I can sit with engineers, executives, and end users and keep the conversation useful: requirements, demos, tradeoff calls, architecture reviews, and clear explanations that help teams make decisions.

Operational Range

SECTOR COVERAGE · FAST CREDIBILITY SCAN

I have shipped across federal, financial services, retail, healthcare, education, manufacturing, small business services, and enterprise technology environments.

Sector Coverage

SELECTED SECTOR EXPERIENCE
SCANNING FEDERAL & DEFENSE FINANCIAL SERVICES RETAIL & E-COMM HEALTHCARE ENTERPRISE TECH SMB & SERVICES EDUCATION MANUFACTURING
SectorSignalEngagements
Federal & DefenseW-2 and subcontractor engagements · DHS · DOJ · DoD · NGA · FDIC
Financial ServicesW-2 and subcontractor engagements · Citizens · FDIC · Elevate Finance Group
Retail & E-CommerceClient and product work · NIKE · InstaMapp · shopdesigns.co · Shopify engagements
HealthcareSubcontractor engagement · HCSC · Defender security engineering
Enterprise TechW-2 roles · Peters & Associates · HARMAN · ByteCubed
SMB & ServicesFounder and consulting work · PC Ingenuity · CloudTect
EducationW-2 teaching and mentorship · Prairie State College · WBLA
ManufacturingW-2 operational technology role · Tufts Grinding

Mission History

FIVE PHASES · SCROLL TO REVIEW · CLICK A CASE TO EXPAND LENS
Current Build2017 – PRESENT

Products & Selected Engagements

CloudTect, a live AI product, private production systems, and selected current client engagements. Public links are included where work is available to view.

CASE-051CommercialInstaMappLive Product

A live AI-enabled SaaS marketplace for collectors: computer vision recognition, OCR, live market pricing, and a social layer with leaderboards. I design and build its recognition and OCR workflows, cloud AI service integrations, backend data flows, API integrations, and production architecture. The approach favors bounded recognition, pricing, and workflow services so AI output is useful without turning every step into an open-ended agent loop. See how it works in the demo below.

Computer visionOCRAPI + tool-calling workflowsAgent workflow evaluationinstamapp.com
CASE-052CommercialGuardrailed AI Repricing PipelineProduction System

A private Shopify repricing system: an LLM can recommend a price, while deterministic policy and validation code control every write. It is an example of applying AI in production with clear guardrails.

ShopifyLLMGuardrails
CASE-053CommercialDCOSMOSIn Build

An in-development business-operations platform. The current work focuses on shared customer and hiring workflows, with AI-assisted matching, drafting, and planning. Broader modules are planned rather than represented as finished product capabilities. See the concept view below.

SaaSCustomer and hiring workflowsAI-assisted matching and draftingdcosmos.ai
CASE-054CommercialEnterprise Bank Security · CitizensSecurity Delivery

W-2 and C2C work supporting Citizens Bank, where I was brought in as the Azure security subject matter expert for the content engineering team. I owned the Azure security product workstream, led Azure-related security efforts, and helped the team adopt Azure Advanced Threat Protection, Office 365 Advanced Threat Protection, and the broader Microsoft security suite. I also took on QRadar work outside the original Azure scope, helping the team write Splunk detection rules as they moved off QRadar. From there, I built an early Detection as Code prototype for Splunk rules, using source control to show file diffs, who changed a rule and when, and to support disaster recovery or rule restoration. Later, I helped implement Microsoft Purview data flowing into Splunk.

Citizens BankW-2 + C2CAzure security SMEQRadar to SplunkDetection as CodePurview to SplunkAzure ATP · O365 ATP
CASE-042FederalCloud Security at Federal Scale · FDICActive Engagement

Publicly discussable summary of a C2C subcontractor engagement supporting FDIC as the end customer: platform security across more than 60 Azure subscriptions. I develop Azure Policy controls against the agency's customized security benchmark, publish reusable PowerShell governance modules, and automated a compliance investigation that previously took about a business day to run in under a minute. The work also includes Splunk correlation searches and AI-governance policy as the agency adopts AI.

FDIC end customerC2C subcontractorAzure PolicyPowerShell governanceSplunk SPLAI governance
CASE-055CommercialDefender Security Engineering · Fortive · HCSC · GuidestoneCompleted

C2C subcontractor engagements supporting Fortive, HCSC, and Guidestone as end customers: deployed and configured Microsoft Defender for Endpoint and Defender for Identity, reducing attack surface across corporate environments. Led Azure ATP implementations for real time threat detection, integrated Splunk and QRadar with the Defender stack across hybrid environments, and built Defender policy and automated security responses across the three end clients.

Fortive · HCSC · GuidestoneC2C subcontractorDefender for Endpoint · IdentityAzure ATPSplunk · QRadar
NOV 2024Intel · Industry
Model Context Protocol (MCP) is introduced, a standard for connecting AI systems to tools and data. I evaluate it where it improves a product workflow.
NOV 2022Intel · Industry
ChatGPT brings AI to the public. Applied AI moves from a research niche into everyday product and business conversations, reinforcing a direction already informed by satellite computer-vision work.
Federal AI & CloudJUN 2017 – 2020

Federal Cloud & Mission Work

Publicly discussable, unclassified career highlights: federal cloud migrations, petabyte-scale imagery data, satellite computer vision, and mission-platform modernization.

CASE-040FederalFederal Cloud & Data · DOJ · NGACloud Modernization

As BlackSpoke's CTO of Cloud, migrated DOJ Justice Management Division datacenter workloads into Azure, then led an NGA team building the agency's data lake. ETL pipelines supported petabyte-scale geospatial data across 30+ sources, reducing manual processing by roughly 60%. I also designed API microservices and data workflows for imagery cataloging using Python, Node.js, Lambda, NiFi, OpenShift, Docker, Terraform, SQL, Oracle, and SQL Server Integration Services (SSIS), with secure-environment deployment practices.

CTO, CloudPetabyte-scale data · 30+ sourcesPython · Lambda · NiFi · DockerTerraformOpenShift · SQL · Oracle · SSIS
CASE-041FederalSatellite Imagery Computer VisionComputer Vision Platform

At BlackSky Technology (NYSE: BKSY), worked on Spectra, an AI-enabled space-intelligence platform that fused satellite imagery with SAR, RF, GPS, and IoT sensor data for object, change, and anomaly detection and site monitoring. The work included PyTorch and TensorFlow detection models, a continued NGA AWS microservices contract, and an IARPA program. This site presents an illustrative, unclassified visualization rather than program materials.

Spectra platformPyTorch · TensorFlowSAR · RF · GPS fusionNGA · IARPA
CASE-043FederalMission AI Platform ModernizationMission AI Platform

A publicly discussable, high-level summary of the largest production AI application I have worked on: a multi-year modernization of an existing cleared mission application. I led two delivery teams rearchitecting services on AWS using Well-Architected principles and loosely coupled microservices behind APIs. My teams owned Python API services end to end; I later worked alongside Java backend services in the same environment. The program operated at petabyte scale, with data warehousing measured in billions of records and continuous structured and unstructured ingest supporting mission-focused AI/ML, computer-vision, and geospatial workflows.

AWS Well-ArchitectedPython REST APIsJava servicesPetabyte scaleBillions of records
JUN 2017Intel · Industry
"Attention Is All You Need" publishes the transformer, the architecture behind every modern LLM. The same month, I started cleared work.
MAY 2017Intel · Industry
WannaCry ransomware hits 200,000+ machines worldwide. That same spring, I supported a NIKE security-roadmap engagement as a C2C subcontractor.
SEP 2016Intel · Personal
Education milestone. I completed a second associate's degree, a bachelor's degree, and an M.S. in Computer Science while working full time.
NOV 2015Intel · Industry
Google open sources TensorFlow. PyTorch follows in 2016. The frameworks I'd later point at satellite imagery become available to everyone.
Enterprise ArchitectureJAN 2012 – JUN 2017

The Architect Years

Lead and principal architecture at rising scale: Peters & Associates (2012–2015), HARMAN Connected Services (2015–2016), ByteCubed (2016–2017), capped by building a five year security roadmap for NIKE. Systems designed to survive contact with real organizations.

CASE-031CommercialDigital Leader Award · HARMANRecognized

IDG and Dimension Data recognized the cloud architecture work at HARMAN Connected Services, where I ran the cloud practice from the first whiteboard to delivery across multiple portfolios.

Principal Cloud ArchitectCloud practice lead
CASE-032CommercialNIKE · 5 Year Security RoadmapSecurity Roadmap

C2C subcontractor engagement supporting NIKE as the end customer. Built a five year technology roadmap for NIKE's corporate information security team covering application security, cloud platform security, encryption and certificate management, vulnerability management, and penetration testing, and integrated CloudWatch, Rapid7, and AlienVault across 40+ Azure and AWS subscriptions.

NIKE end customerC2C subcontractor5 year security roadmap40+ subscriptions
CASE-033FederalBig Data for DHS · ByteCubedBig Data Platform

As ByteCubed's Principal Big Data Architect, led an engineering team building big data platform solutions at scale, with DHS among the customers served. Owned software architectures, coding standards, code reviews, and the technical direction that kept feature delivery on time.

DHSEngineering team leadBig data platforms
CASE-030EducationAdjunct Professor · Prairie State CollegeAdjunct Teaching

Eleven years teaching nights while building days: Visual Basic, Java, C#, C++, and Ethical Hacking, plus a seat on the IT advisory board. Also served as an exam development Subject Matter Expert for CompTIA and Microsoft. Explaining systems is how you find out if you understand them.

VB · Java · C# · C++Ethical HackingCompTIA & Microsoft exam SME
2012Intel · Industry
AlexNet ignites the deep learning era. Computer vision stops being sci-fi. I'm architecting at enterprise scale as it happens.
JUN 2011Intel · Industry
Microsoft launches Office 365. The migration wave that follows defines my architect years, moving clients off Google Apps and on prem Exchange into the cloud.
FEB 2010Intel · Industry
Microsoft launches Azure, the platform I would go on to secure across 60+ federal subscriptions.
Founder & Client Delivery2008 – 2012

First Company

Founded PC Ingenuity during the financial crisis and built it through client development, scoping, delivery, and support.

CASE-020CommercialPC Ingenuity · FounderFounder Delivery

My own shop: custom desktop, web, and mobile apps for small and medium businesses, SharePoint and ASP.NET builds, network design, and cloud work that was early for its time: refactoring client applications to run in AWS and Azure and standing up DevOps pipelines for them. The anchor engagement was running IT for a group of eight affiliated companies, migrating all 300 users off Lotus Notes onto hosted Exchange 2007, and replacing their aging Access/SQL ERP with a Java and Oracle system with handhelds, cutting real cost in a crisis economy.

ASP.NETSharePoint8 company engagementERP modernizationEarly cloud refactors
SEP 2008Intel · Industry
The financial crisis hits. I founded PC Ingenuity into the teeth of it. The anchor client was a group of eight companies that needed cost cut, and the ERP modernization paid for itself.
2006Intel · Industry
AWS launches EC2 and S3. The cloud era begins. I'm working my way from the shop floor to a one man IT team, learning firsthand what the cloud would eventually replace.
MAY 2005Intel · Industry
Windows Mobile 5.0 ships and barcode handhelds hit the warehouse mainstream. My inventory app ran on exactly that stack: VB.Net on a Windows Mobile scanner reading barcoded labels.
2005Education · Personal
ITT Technical Institute milestone. This early technical training sat alongside the hands-on shop-floor automation work that moved me from operations into software and IT.
2003Intel · Industry
Walmart mandates RFID for its top suppliers, the same technology I'd put on Tufts Grinding's shipping floor to streamline outbound freight.
2003Education · Personal
High school graduation. I was already working at Tufts Grinding, learning the business from the shop floor before moving deeper into IT and software.
FEB 2002Intel · Industry
Microsoft ships .NET Framework 1.0. Eight months later I started at Tufts Grinding, and .NET became the platform I built my first production software on.
Education & Technical FoundationOCT 2002 – NOV 2008

From the Crane to the Code

My last year of high school, I ran an overhead crane at Tufts Grinding, loading machines and flatbed semis. The company ran on the Toyota Way and 5S: promote from within, understand the whole process. So they rotated me through every department: shipping and receiving, then every IT problem in the building. Once I understood how the whole business worked, I became a one man IT team and built the automation software that supported it. I later supported Tufts as a client and helped transition IT back into internal operations. Twenty years later, that same idea became DCOSMOS: learn the whole business, then build one system that runs it.

CASE-010CommercialShop Floor AutomationDelivered & Transitioned

Started at Tufts Grinding as a W-2 employee, moved from shop-floor operations into IT and software, and built VB.Net inventory tools on Windows Mobile 5.0 with SQLite and barcoded labels, RFID on the shipping floor, bash scripts for supply-and-demand processing, and VMware virtualization. Later, Tufts became a client, and I supported them through consulting work before helping transition IT back into internal operations.

VB.NetSQLiteRFIDBarcodeVMware

Loadout // Capabilities

WHAT I BRING TO AN ENGAGEMENT
CAP-01

AI & Computer Vision

PyTorchTensorFlowObject detectionChange detectionOCRClarifai
CAP-02

Applied AI Platforms

LLM + tool-calling workflowsAgent workflow evaluationModel Context Protocol (MCP)Token routingGuardrail architectureAI governance / TEVVCost attribution & observabilityModel lifecycle managementBuild versus buy for AI
CAP-03

Cloud & Security

AzureAWSGCPCloud security architecturePowerShell automationZero TrustIdentity and access management (IAM)Microsoft Defender · Sentinel · PurviewData-platform leadership
CAP-04

Engineering & Delivery

PythonPython REST APIs.NETAI service integrationToken-based API securityProduction troubleshootingShopifyDocker · KubernetesData platforms
CAP-06

Technology Leadership & Executive

Technology vision & strategyEngineering organization leadershipBuild versus buy & vendor managementIT governanceBudget & portfolio ownershipRoadmappingNIST · Azure Security Benchmark · SOC 2-aligned practicesEnterprise AI platform & LLMOps ownershipAzure AI Foundry · Claude Enterprise · ChatGPT EnterpriseTechnology change management & operating model transformationExecutive & client communicationTeam building & mentoring
CAP-05

Credentials

TS/SCI clearance · CI polygraphFDIC Public TrustM.S. Computer ScienceAzure Solutions Architect · Microsoft Certified Solutions Expert (MCSE) CloudAWS Certified Cloud PractitionerCompTIA certifications · A+ · Network+ · Security+ · Cloud+ · Mobility+SAFe Scrum MasterCompTIA & Microsoft exam SME

CASE-051 // How InstaMapp Works

LIVE PIPELINE · THE SAME FLOW EVERY USER RUNS
INSTAMAPP · RECOGNITION PIPELINEIDLE
OBJECT IDENTIFIED · COLLECTIBLE CARD
COMP #1
SOLD 6D AGO
COMP #2
SOLD 2D AGO
COMP #3
ACTIVE LISTING
YOUR ITEM
EST. RANGE
RESULT: PRICED & LISTED. From photo to marketplace in one flow.
Project stack: computer vision · machine learning · OCR · Clarifai · token routing · live market pricing
STEP 01
Scan

The user snaps a photo of their item. No forms, no typing.

STEP 02
Recognize

Computer vision identifies the object and locks on.

STEP 03
Extract

OCR and the recognition model pull the details: name, set, attributes.

STEP 04
Check the market

Live pricing compares recent sales and active listings for the same item.

STEP 05
Price & list

The user gets a value range and can list to the marketplace instantly.

This is a simplified visualization with sample values. The real thing is live at instamapp.com. Under the hood: a recognition pipeline, OCR flow, and token routing I built to keep inference costs sane.

CASE-053 // How DCOSMOS Works

TWO LIFECYCLES · ONE PLATFORM · CLICK A PIPELINE STAGE FOR DETAIL
DCOSMOS · CUSTOMER LIFECYCLEIN BUILD · CONCEPT VIEW
WEB FORM MARKETPLACE REFERRAL AI · SOURCE/MATCH AI · DRAFT COMMS AI · PLAN & PROMOTE
Current focus: shared customer and hiring workflows · AI-assisted matching and drafting · cloud-hosted SaaS
CASE-053 // The DCOSMOS Thesis

DCOSMOS is an in-development business-operations platform. The current work focuses on shared customer and hiring workflows: moving a lead or candidate through the right steps, with AI-assisted matching, drafting, and planning where it adds value. Broader modules are planned rather than represented as finished product capabilities. In build at dcosmos.ai.

Choose Your Engagement

SELECT ONE OR MORE OPTIONS · THE FORM ADAPTS TO YOUR NEEDS

Available to start quickly. Timing can be adjusted to your needs. · Open to W-2 employment and company-to-company (C2C) consulting based on scope, duration, and fit.

Start here · Engagement inquiry

How Would You Like to Work Together?

01 · Choose one or more options
Path 01 · Full-Time Role
Select

Hire Me Full-Time

For a permanent role in AI engineering, cloud, security, architecture, or hands-on technology delivery.

ResumeEngineering & Delivery
Path 02 · Consulting Project
Select

Engage My Firm

For a project or ongoing consulting engagement delivered directly through CloudTect.

ResumeEngineering & Delivery
Path 03 · Technology Leadership
Select

CTO / Technology Leadership

For full-time, fractional, or interim leadership to set strategy, guide teams, strengthen governance, and improve delivery.

ResumeTechnology Executive
Select one or more options above to continue.
Inquiry received

Check Your Inbox

The resume selected for your inquiry is on its way. I will review your message and respond personally within one business day.

Public Template

Clone The Template

Most of what I have built across 23 years lives behind clearances and client walls. It was never mine to show. This site is one thing I can give back. The satellite view, mission-themed timeline, theme switcher, and private-content deployment pattern are available on my GitHub. Clone it, adapt it, and make it yours under the repository's MIT license. If this helps you land something, that's the mission.

This site: Astro static site · hand coded SVG · JavaScript · CSS custom properties