Remote · Eastern Time (US)

Erick E. Shepherd

Enterprise Software Engineer · Oracle Ecosystems · AI-Assisted Tooling

Enterprise software engineer specializing in Oracle APEX, PL/SQL, and AI-assisted developer tooling. NASA Goddard alum.

Experience

Recent work

A decade across enterprise Oracle development, defense systems engineering, and NASA Earth-science research.

Aug 2021 – May 2026

Application Development Advisor

Cigna Supplemental Health Services (via Magnit Global) · Remote

Lead and core developer on the Oracle APEX applications powering a national supplemental-health-insurance underwriting pipeline, from quoting through contract generation.

  • Lead developer on the Field Quote Tool — the entry point of the underwriting pipeline used daily by sales, pricing, and underwriting teams — and core developer on Engage, the downstream contract-generation tool, across the full tenure.
  • Introduced Git and GitHub to a team with no source control, establishing the branching, code-review, and commit standards adopted across the group, with admin over 29 repositories.
  • Co-designed the team's first CI/CD pipeline and led the Oracle APEX deployment-workflow integration.
  • Designed and built MAKESQL, a domain-specific language and Python package that compiles PL/SQL objects in correct dependency order across environments — replacing an error-prone manual process — plus a companion VS Code syntax-highlighting extension.
  • Built a Python abstraction layer over the OracleDB environments that let Claude, via Cursor Composer, query enterprise databases through a locally-running credentialed utility — one of the team's first production AI integrations.
  • Authored an OCR-backed ETL pipeline using pandas and pytesseract that migrated inconsistently structured Excel pricing data — including rate tables embedded as images — into Oracle on upload.
  • Mapped dependencies across 15+ applications and hundreds of database objects with graphviz and networkx into architectural reference graphs delivered to leadership.
  • Led a four-developer squad: task delegation, code review, and technical direction.
  • Oracle APEX
  • PL/SQL
  • Oracle Database
  • Python
  • Jenkins
  • GitHub
  • Liquibase
  • pandas

Jul 2020 – Jun 2025

Freelance Systems Engineer

Independent · Remote

Independent contract engineering spanning embedded/IoT devices and web and data systems.

  • Designed and prototyped IoT security devices: embedded firmware in C and Python, custom PCB design, and sensor integration.
  • Delivered smaller contracts across web development, data automation, and systems integration.
  • C
  • Python
  • Embedded firmware
  • PCB design
  • Sensor integration

Jun 2020 – May 2021

Radar Systems Engineering Intern

Northrop Grumman Mission Systems · Baltimore, MD

Systems engineering within a cleared defense environment.

  • Worked inside a cleared facility on large-scale defense systems-engineering processes, documentation standards, and cross-functional workflows.
  • Held an active DoD Secret clearance (obtained April 2020; lapsed 2021, eligible for reinstatement).
  • Systems engineering
  • MATLAB

View full experience

Projects

Selected projects

Things I've built outside of client work — AI tooling, geospatial systems, and self-hosted infrastructure.

Walter — AI Voice Assistant

A pre-LLM voice assistant with speech-to-text, text-to-speech, and natural-language processing, plus OpenCV facial recognition — built well before the current AI wave.

  • Python
  • OpenCV
  • nltk
  • speech_recognition
  • pyttsx3

BAT Powerwall — Geospatial Service-Mapping System

An interactive touchscreen mapping and service-alert system for a septic-services business: reverse-geocoded a customer spreadsheet into a filterable Folium map with pricing zones, service-due heatmaps, and upsell alerts, displayed on a repurposed big-screen TV fitted with an infrared touch overlay.

  • Python
  • Folium
  • geopy
  • pandas

HackGPT — Security Research GPT

A custom GPT for malware-source analysis in cybersecurity research; credited as a named contributor in the SANS HackFest 2023 presentation on enhancing red teaming with AI and ML.

  • Custom GPT
  • LLM tooling
  • Security research

All projects

Contact

Let's work together

Open to remote roles and freelance engagements in Oracle, health IT, and developer tooling.

dm@erickshepherd.com