Building the Web with Ruby on Rails Since Its Inception.
20 years of experience driving outcomes for Healthcare, Academia, and E-Commerce giants.
Work History & Narrative
A two-decade narrative of craft and commitment
Timeline Index
Luthor AI (Y-Combinator F24)
AI-powered Fractional Compliance Services
Core full-stack developer on Luthor V2, an AI-powered compliance platform. Built Rails 8 services with Solid Queue and PostgreSQL for document processing and automated regulatory disclosure detection. Led development of secure vault archiving with cloud storage and content exports to PDF, DOCX, Markdown, and text. Integrated OpenAI and Chunkr OCR APIs into the platform's document workflows.
Plum Co-Ownership
Venture-backed vacation platform
Led technical development of Plum Web, a Rails 7.1 marketplace for vacation home co-ownership. Built the Dreamboard property preference engine, a public marketplace with MLS integration, and collaborative proposal tools. Developed custom JavaScript web components and Tailwind CSS interfaces, established the PostgreSQL architecture, and migrated deployment to containers with Kamal on DigitalOcean.
WingTask (UI Refresh)
Product Overhaul
Redesigned the mobile interface for WingTask, my independently built companion to the Taskwarrior command-line task manager. Replaced Material Components with custom web components, giving the product its own visual identity and a consistent experience for both iOS and Android users.
1bios
Healthcare Monorepo
Developed a suite of Rails applications serving different user groups on a healthcare platform. Built a Rails and React administration interface and a React mobile frontend backed by a Rails API. Worked across multiple Rails apps in a shared monorepo, connected through a common Ruby library.
WingTask (Initial)
Solo Product Build
Designed, built, and deployed WingTask independently, taking a mobile Taskwarrior companion from Sketch designs to a working product. Paired an Elm frontend with a Rails API and PostgreSQL, and wrote a custom Ruby gem to execute Taskwarrior commands. Provisioned and hosted the application on Linode using Chef.
Bidsketch
Docsketch Development
Developed the document preparation interface for Docsketch, an electronic signature application in development at Bidsketch. Built a React interface that let users drag signing elements onto uploaded documents, using React DnD and the HTML5 drag-and-drop API to support precise placement.
TaxJar
Sales Tax Automation
Created the initial TaxJar Ruby API wrapper, giving Ruby developers a way to integrate TaxJar's sales tax services into their applications. The work supported a platform helping online sellers and merchants manage sales tax filing.
Econify
Marketplace Tech
Developed features and resolved bugs for an industrial parts marketplace through Econify, a software consultancy. Worked within an existing application built around an eBay-style model for buying and selling large machinery parts.
Endpoint / Harvard Law
H2O Platform
Built document annotation features for Harvard Law's H2O platform while working with Endpoint. Enabled professors to annotate course materials and share them with a class, while students could add their own annotations. Implemented versioning support for the annotation workflow.
Morlen Sinoway
E-commerce Launch
Launched a Spree ecommerce store for Morlen Sinoway, a Chicago contemporary furniture retailer. Used the Rails commerce platform to bring a catalog of furniture, contract lighting, home accessories, and custom area rugs online.
Soletron
Social E-commerce
Replaced Spree's default search with Solr for a marketplace focused on designer sneakers. Built a faceted search interface that let shoppers narrow products by color, size, price, and shoe type, making the catalog easier to explore.
Paradise Marketing
Wholesale Migration
Built a Spree ecommerce store for a major US wholesaler of sexual wellness products. Wrote custom import scripts to load its extensive product catalog into the Rails commerce platform as part of the store launch.
Cosas de Regalo
Barcelona E-commerce
Upgraded a Barcelona gift and home decor retailer's Spree store from Rails 2 to Rails 3. Adapted the application through major changes in both frameworks while preserving the regional tax and shipping behavior the business depended on.
Currix
Education Marketplace
Customized Spree into a marketplace where teachers could discover educational resources. Built seller administration pages for uploading content and automated previews: first pages from PDFs, 15-second video clips, and audio samples that buyers could review before purchasing.
Recruit Military
Military Job Board
Built a Spree ecommerce storefront for Recruit Military, a subsidiary of Bradley-Morris connecting employers with military job seekers. Applied the Rails commerce platform to the recruiting company's online store.
Novawhite
Singapore E-commerce
Integrated a custom credit card payment gateway for Novawhite, a Singapore teeth whitening company. Addressed payment processing issues affecting US customers, connecting the store's checkout to the gateway needed to support those transactions.
thoughtful
Recommendation Service
Developed product display features for Thoughtful, a gift recommendation service offered through web and mobile applications. Worked on the customer-facing presentation of products within the service's gift discovery experience.
Rise Clothing
Sports Fitness Brand
Built Rise Clothing's first Spree store for its sports and fitness apparel business. Implemented clothing variants and connected inventory data from a third-party REST API, bringing external stock information into the online catalog.
Pernod Ricard USA
Spirits & Wine CMS
Maintained and extended a Rails content management site for Pernod Ricard USA through a design firm. Delivered ongoing content updates and new CMS features, including age-verification dialogs for the spirits and wine company's website.
City Winery
Complex Event E-commerce
Delivered an online store combining live event ticket sales and shipped merchandise for City Winery in New York. Built seat selection with tiered pricing for a 500-seat venue, event sales cutoffs, and an integrated CMS. Took over delivery and completed the project independently after the original contractor fell short.
Socrata
Database Optimization
Investigated slow pages on Socrata's government data platform and optimized the Ruby code and SQL behind them. Moved expensive filtering and sorting from Ruby arrays into PostgreSQL, and added targeted indexes, including compound indexes, to improve query performance.
Vulcan Labs / Gist
Email Importer
Developed core email importing from IMAP and Gmail for Gist, an email aggregation tool. Built parsing logic to extract addresses and URLs and analyze attachments. Prepared the resulting data for a dashboard showing attachments and a 3D visualization of email relationships.
Universal Music Group
Mobile Transactions
Built a Rails application for a Universal Music Group subsidiary selling ringtones and mobile content. Integrated with an existing Java backend to support purchases through SMS transactions. Later developed a separate ringtone application for Skype.
Ruby on Rails Transition
The Pivot
Adopted Ruby on Rails in 2005 while building an application stack in .NET. Its approach to database-backed applications changed how I wanted to build software and became the focus of my career. Shared the transition in an early .NET-to-Rails story picked up by the community.
Stop Loss Insurance Inc.
Insurance Support
Worked at a brokerage specializing in stop loss insurance for hospitals. The business focused on coverage for rare, high-cost cases and the financial exposure they created for healthcare providers.
RSM Equico
M&A Tech
Worked alongside the in-house development team at RSM Equico, an investment bank advising on mergers and acquisitions. Built features for workflow management software that tracked deals through successive stages and across departments.
Piaggio USA
Warranty Claims
Built a Windows application to manage dealer warranty claims for Piaggio USA. Integrated data from the Great Plains system and supported the process from claim tracking through approval and dealer payment, connecting financial records with day-to-day warranty operations.
Technical Toolkit
Langs & Frameworks
- Ruby on Rails
- Ruby
- Hotwire
- Vanilla Javascript
- Elm
- React
- Typescript
Frontend
- Design Systems
- CSS
- Accessibility
- TailwindCSS
- Web Components
Infrastructure
- Kamal Deployment
- PostgreSQL
- Docker / Containers
- Redis
- Solr / ElasticSearch
- Linux / VPS
Testing & Tools
- Minitest / RSpec
- Mocha / Chai
- Chef / Prometheus
- DB Optimization
- API Integration
LLM / AI
- LLM Pipelines with ActiveJob
- Prompt Engineering with Structured Output
- RAG
- Agent coding tools
WingTask
Case Study: Solo Full-Stack Build
Solo conceived and created project demonstrating full-cycle ownership. Features Elm frontend, Rails API, and Chef-provisioned hosting.
