Signal
Mission Brief // File 001

Andrew
DiCosmo

Open to the Right Opportunity
Andrew DiCosmo
SUBJECT:   Engineering Leader, Principal Architect & Hands On Builder
FOCUS:     Technology leadership · AI · Cloud · Data · Security · Software Modernization
CLEARANCE: TS/SCI w/ CI Poly
LOCATION:  Greater Chicago Area · Northwest Indiana
KNOWN FOR: understanding the operation, setting technical direction, and owning delivery through production
Available Engaged
Open to engineering, architecture, management, and select executive roles, plus consulting engagements
PASS 2026.08 · 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. At FDIC, I turned cloud compliance from a manual analyst procedure into an automated control, evidence, and remediation workflow across more than 60 Azure subscriptions. I have also owned enterprise AI platform planning across Azure AI Foundry, Claude Enterprise, and ChatGPT Enterprise, including model selection 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. I build AI systems the same way I build compliance automation: models can assist, but deterministic policy, validation, and auditability control the outcome.

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 ServicesC2C → W-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 Products & Recent Work2017 – PRESENT

Products & Selected Engagements

CloudTect, a live AI product, production systems, and selected recent client engagements. Open product links are included where available.

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 workflowsTool-calling workflowsAgent workflow evaluationinstamapp.com
CASE-052CommercialGuardrailed AI Repricing PipelineProduction System

A private Shopify repricing system where an LLM recommends prices, but deterministic policy and validation code control every write. The model gets an opinion; the guardrails get the final say.

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. Additional modules are on the roadmap. See the concept view below.

SaaSCustomer and hiring workflowsAI-assisted matching and draftingdcosmos.ai
CASE-054CommercialCitizens Bank · Azure Security Engineering2023–2026 · Contract-to-hire

After BlackSky ended in March 2023, Citizens Bank became my primary role. The work began through a company-to-company engagement and later converted to W-2, effectively a contract-to-hire progression. I served as the Azure security subject matter expert for the content engineering team, owned the Azure security product workstream, and supported adoption of 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, helped the team write Splunk detection rules during the migration from QRadar, and built an early Detection as Code prototype that used source control for change history, recovery, and rule restoration. Later work included Microsoft Purview data flowing into Splunk.

Citizens BankC2C to W-2Contract-to-hireAzure security SMEQRadar to SplunkDetection as CodePurview to SplunkAzure ATPO365 ATP
CASE-042FederalCloud Security at Federal Scale · FDICCompleted

Completed C2C subcontractor engagement supporting FDIC as the end customer across more than 60 Azure subscriptions. I encoded the agency's customized security benchmark into Azure Policy controls, built reusable PowerShell governance modules, and operationalized the process through GitHub Actions. The workflow checked configuration drift, generated compliance evidence, updated findings, supported remediation, and reduced analysis that could take most of a business day to under a minute. The result was a repeatable compliance engineering process instead of a manual point-in-time investigation. The work also included Splunk correlation searches and AI-governance policy as the agency adopted AI.

FDIC end customerC2C subcontractorAzure PolicyPowerShell governanceGitHub ActionsCompliance automationDrift detectionControl evidenceRemediation workflowsSplunk 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.

FortiveHCSCGuidestoneC2C subcontractorDefender for EndpointDefender for IdentityAzure ATPSplunkQRadar
Federal AI & CloudJUN 2017 – 2024

Federal Cloud & Mission Work

Federal cloud migrations, petabyte-scale imagery data, satellite computer vision, and mission-platform modernization across DOJ, NGA, DoD, BlackSky, and FDIC work.

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

As BlackSpoke's cloud lead, migrated DOJ Justice Management Division datacenter workloads into Azure. On NGA's Corporate Analytic Visualization Environment (CAVE) program, I helped the NGA team understand, maintain, and build out a data warehousing platform after the prime contract win while also leading two teams that built mission microservices. The BlackSpoke work included hands-on software development for API-backed microservices, imagery cataloging, retrieval, and data-access workflows supporting computer vision, geospatial, and intelligence use cases. Earlier BlackSpoke and BlackSky services ran as Kubernetes-based microservices on EC2 and migrated to AWS EKS as the EKS environment came online. Later, through CloudTect work for NGA under BlackSpoke, we migrated a web/API/database microservice from Kubernetes containers to OpenShift, changing deployment from Terraform-managed infrastructure to Docker images, Helm, private container repositories, and GitLab runners. The platform work also used Prometheus, Grafana, Kibana/Elasticsearch, Lambda, NiFi, SQL, Oracle, and SQL Server Integration Services (SSIS), with ETL and API workflows supporting petabyte-scale geospatial data across 30+ sources.

Kubernetes on EC2 -> EKSKubernetes containers -> OpenShiftSoftware developmentAPI-backed microservicesImagery catalogingRetrieval workflowsData-access workflowsDockerHelmPrivate registryTerraformGitLab runnersCI/CDPrometheusGrafanaKibana/ElasticsearchData warehousingLambdaNiFiSQL
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. Platform work used EKS-based microservices, Docker, Helm, Prometheus, Grafana, Kibana/Elasticsearch, and Airflow to monitor container performance, tune CPU utilization, and support scaling decisions. The visual on this site is an original illustration, not client material.

Spectra platformPyTorchTensorFlowEKSDockerHelmPrometheusGrafanaAirflowSARRFGPS fusion
CASE-043FederalMission AI Platform ModernizationMission AI Platform

The largest production AI application I have worked on was 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
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-031CommercialSherlock AI · Digital Leader AwardAward

At HARMAN, I led the architecture and application design for the original Sherlock AI product and worked hands-on with two other talented developers to build it as a rapid prototype. Sherlock AI combined data scraping, machine learning, and predictive analytics to analyze market signals for build-versus-buy decisions and guide R&D investment. The platform continued in internal use after my departure. Built on Microsoft cloud services, Sherlock AI received a 2016 Digital Leader Award from IDG and Dimension Data.

Read the award coverage
Product architectureHands-on developmentMachine learning & predictive analyticsR&D decision support
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.

VBJavaC#C++Ethical HackingCompTIA & Microsoft exam SME
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
Education & Technical FoundationOCT 2002 – NOV 2008

From the Crane to the Code

I started at Tufts Grinding during my last year of high school as a material handler, operating an overhead crane and side loader to load machines and trucks. While attending night school for Computer Science, I kept shop-floor computers running when failures threatened production. Management then moved me into shipping and receiving and, at the same time, assigned me responsibility for the company's IT work because no formal internal IT department existed. As the next generation of owners introduced Toyota Way-inspired continuous improvement, I rotated through purchasing, production, shipping, costing, and invoicing to understand the operation and find bottlenecks worth fixing.

CASE-010CommercialShop Floor AutomationDelivered & Transitioned

Handled the complete internal technology function, from break-fix support and infrastructure through ERP workflows and custom software. I built a validated material-record system and connected it to ERP shipping output, eliminating a tedious manual printing step and saving approximately 80 to 125 hours per year. I also automated plant-manager job-cost review from roughly one hour per job to a button-driven process across approximately 15 to 30 completed jobs per day, making profitability problems and data-entry errors visible much sooner. After leaving as a W-2 employee, I continued providing part-time and occasional onsite support for roughly 15 years, then helped train and transition responsibility to the internal IT team.

Internal IT ownershipShop-floor supportValidated material recordsERP shipping automation80–125 hours saved annually15–30 jobs reviewed dailyLong-term support and handoff

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. Additional modules are on the roadmap. In build at dcosmos.ai.

Choose Your Engagement

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

Open to select opportunities. · Considering senior technology leadership roles 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

Engineering or Architecture

For an individual contributor role in AI engineering, cloud, security, architecture, or hands on technology delivery.

ResumeEngineering & Delivery
Path 02 · Management Role
Select

Manager or Director

For a people, platform, engineering, architecture, or technology management role with delivery ownership.

ResumeArchitecture & Leadership
Path 03 · Consulting Project
Select

Engage My Firm

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

ResumeEngineering & Delivery
Path 04 · Executive Leadership
Select

Executive or Fractional

For CTO, CIO, VP, Head, Chief Architect, fractional, or interim mandates with enterprise authority.

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.

Free on GitHub

Build Your Own Mission Site

This portfolio is available as a free, reusable GitHub template. Download or fork the public repository, replace the example content, and deploy your own version. Personal content stays separate from the template, and the code is available under the MIT license.

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