Doug Headley
Verified Expert in Engineering
Software Engineer and Developer
Olympia, WA, United States
Toptal member since December 30, 2025
Doug is a senior software engineer specializing in secure system design, full-stack development, and automation. He is an expert in crafting robust security architectures, developing scalable APIs, and guiding data-intensive solutions to optimize operations and boost efficiency. With extensive experience in modern DevOps, cloud infrastructure, and application security, Doug is proficient in converting complex business requirements into secure, sustainable, and high-impact solutions.
Portfolio
Experience
- Linux - 20 years
- HTML5 - 20 years
- Bash Script - 12 years
- Ruby - 12 years
- Ruby on Rails (RoR) - 12 years
- Docker - 10 years
- Ember.js - 9 years
- PostgreSQL - 8 years
Preferred Environment
Omarchy, Bash, Doom Emacs, Tmux, Twilio API
The most amazing...
...thing I've developed is a Kubernetes cluster to host applications from a server rack in my garage. It is connected to cloud resource nodes through a custom VPN.
Work Experience
Infrastructure Engineer
SureCo
- Increased productivity by automating large-scale data operations, generating millions of SQL records.
- Automated data synchronization between DynamoDB and Zendesk, significantly reducing manual entry.
- Managed AWS-based pipelines using Lambda, S3, and FTP for automated external data exports.
Software Engineer
Eliassen Group
- Designed and built a "dynamic converter" ETL pipeline for varied hospital data ingestion.
- Enabled AI model training by creating grammar logic for the data science team.
- Owned back-end APIs and matured code into OO components with test coverage.
Senior Rails Engineer
Covermymeds
- Led a successful Ruby on Rails upgrade and test suite overhaul.
- Developed a risk mitigation framework for code deployments.
- Facilitated the unblocking of Okta authentication integration.
Security Engineer
uber
- Automated vulnerability testing environments using isolated VMs.
- Implemented SemVer patch automation for safe, non-breaking security updates.
- Partnered with engineering teams to embed security into CI/CD workflows.
Senior Engineer
POSaBit
- Developed a secure payment library for the Litecoin wallet to secure all point-of-sale transactions.
- Addressed security vulnerabilities in line with OWASP guidelines to meet state auditor requirements.
- Mentored junior developers across various software disciplines.
- Collaborated with the Android team to establish scalable API communications.
- Designed and implemented API integration software for managing external services for attracting customers with different rewards campaigns.
Senior Rails Engineer
G2 Risk Solutions
- Spearheaded the effort to get Ruby on Rails project to production.
- Implemented new, highly detailed reporting features for customers, enhancing their data analysis capabilities.
- Constructed internal validation tools inspecting reporting data mid-processes.
Senior Software Engineer
ReedHein and Associates
- Designed and implemented a migration strategy to transfer historical customer interaction data from Zoho to Salesforce.
- Developed efficient OOP features in Apex for calculation, reporting, and adjustment of sales commissions.
- Devised a cost-effective, salesforce native solution for managing customer files, resulting in significant monthly savings by eliminating the need for 3rd-party services.
Senior Rails Engineer
Evident.io
- Created event-driven alerting software that efficiently detected resource changes, triggering security audits for enhanced protection.
- Led a team of three in offensive security and test automation, resulting in improved auditing, remediation, and documentation processes.
- Upgraded Rails software stack and gems, optimizing security measures, boosting speed, and ensuring seamless compatibility with new features.
Rails Developer
One to the World
- Increased security, speed, and feature compatibility by upgrading the software stack.
- Created a real-time audience participation feature allowing streaming participants to participate in group chat.
- Implemented improvements to the live polling feature, fixing bugs and adding enhancements.
Junior Developer
VenueLabs
- Coordinated and executed the design of two APIs for iPhone and sentiment-analysis/machine-learning software.
- Created internal services, including email notification, CSV to API data manipulation, and Software data migration for switching 3rd-party services.
- Authored multiple screen-scrappers for social media collection and normalization.
Experience
Career Caddy
https://careercaddy.onlinePersonal Blog about Technology and AI
https://dougheadley.comFedirated YouTube Alternative
Utilizing Caddy as a reverse proxy, video.passiveobserver.com efficiently manages traffic, ensuring high availability and security through TLS encryption. Its Docker-based infrastructure enables scalable and rapid deployment, with Tailscale used for remote volume mounting to further optimize operational expenses.
This setup underscores the platform’s commitment to decentralization, user autonomy, and transparent development. By enhancing scalability and maintaining stringent privacy practices, video.passiveobserver.com empowers content creators, allowing them to retain control over their content in a cost-effective manner. This makes it an ideal solution for individuals and organizations seeking a modern, decentralized approach to video sharing within the Fediverse player.
Education
Bachelor's Degree in Public Relations
Washington State University - Pullman, WA, USA
Certifications
CISSP
(ISC)^2
Skills
Libraries/APIs
REST APIs, API Development, SQLAlchemy, React, D3.js, Playwright, JSONAPI::Resources, Backbone.js, Twilio API, Node.js, Pandas
Tools
Git, AWS IAM, Claude Code, Amazon Cognito, Caddy Server, WireGuard, Tmux, Pytest, Jenkins, Amazon Simple Queue Service (SQS), Amazon Simple Notification Service (SNS), Terraform
Languages
Python, Ruby, HTML5, Bash, JavaScript, CSS, SQL, Bash Script, Snowflake, Go, TypeScript, CoffeeScript
Frameworks
Ember.js, Ruby on Rails (RoR), Django, Flask, Doom Emacs, Ruby on Rails 4, Ruby on Rails 5, gRPC
Paradigms
ETL, Unit Testing, Hosting, Automation, Continuous Delivery (CD), Continuous Integration (CI), Testing, Event-driven Architecture
Platforms
Docker, Linux, Amazon Web Services (AWS), AWS Lambda, Kubernetes, Amazon EC2, Salesforce
Storage
PostgreSQL, Data Integration, Redis, Neo4j, Elasticsearch, MySQL, Data Pipelines, Amazon S3 (AWS S3), Amazon DynamoDB
Other
Security, APIs, RESTFul APIs, Full-stack, API Integration, API Design, Web Scraping, Back-end, API Management, Migration, Data Management, Scripting, FastAPI, Full-stack Development, Business Process Automation, Point of Sale, Website Data Scraping, Infrastructure, Automations, Authentication, Omarchy, Journalism, Mass Media, ChatGPT API, ChatGPT Prompts, FTP/S, Cloud, CI/CD Pipelines, SSH, DNS, Reverse Proxy, Web Analytics, VPS, Litecoin, Security Audits, Zoho, Optical Character Recognition (OCR), ApexPages, NIST, WebSockets, AI Automation, Deployment
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