Jason L Cachia
Ruby on Rails Engineer & Technical Leader
(941) 202-3922 | North Port, Florida
education
Lansing Community College
Electronics Engineering
Votech Honor Society President
summary
Staff/Principal-level Ruby on Rails engineer with 9+ years shipping production Rails and 20 years in technology, from legacy Rails rescue and LLM integration to high-traffic marketplace platforms, with the leadership range to direct teams and contractors when a project needs it.
work experience
- Joined as the first employee on the founding team to build a micro-journal and memory application from scratch, owning engineering leadership, architecture, and hands-on delivery.
- Architected and maintained a Sidekiq and Redis/Valkey-based background job system powering asynchronous OpenAI/Anthropic API calls, Twilio SMS delivery, and Stripe billing reconciliation.
- Architected and developed the application using Ruby on Rails, Hotwire, and Stimulus, delivering a modern, responsive user experience.
- Designed and managed integrations with OpenAI and Anthropic APIs to generate personalized insights and reflections from user journal entries.
- Designed and built a two-way SMS journaling system via Twilio, allowing users to submit entries by text and receive AI-generated contextual acknowledgments in real time.
- Architected an AI-driven SMS quiz feature that periodically challenges users to recall past journal entries and responds dynamically based on their answers.
- Enabled search over ActiveRecord encrypted journal entries by generating LLM embeddings on save and using vector similarity search to surface related entries.
- Architected and built the end-to-end Stripe subscription billing system: inbound and outbound API integration, pricing and plan management, free trials, cancellations, and account reconciliation. Also manage AWS S3 integration for media storage.
- Expanded scope to architect a second product for the same founding team: a pre-launch marketplace platform connecting homeowners planning renovations with vetted contractors, powered by AI-generated project estimates and visions, including a CRM-style tool for contractors to manage customer communication, budgeting, scheduling, and full project lifecycles.
- Authored and maintained the CI/CD pipeline from scratch using GitHub Actions, ensuring reliable deployments and automated testing with Minitest, Selenium and Shoulda.
- Authored and managed the render.yml infrastructure configuration, defining and version-controlling the platform's full cloud environment on Render.
Infinite Computer Solutions
Senior Software Engineer - RoR Modernization
Apr 2024 - Apr 2025
- Contracted part-time to modernize Gannett's large fleet of legacy systems, migrating end-of-life RHEL and CentOS hosts to current CentOS Stream on new infrastructure.
- Brought Rails applications forward across a wide range of legacy Ruby and Rails versions in a high-availability, failover environment that had gone years without upgrades.
- Assessed and remediated significant version drift across the aged fleet, planning and executing per-system migration paths without disrupting production operations.
- Served as a principal engineer on a high-traffic, two-sided Ruby on Rails e-commerce and CRM marketplace connecting thousands of caregivers with families seeking care.
- Member of the Architecture Guild, producing ADRs for the entire organization.
- Led development for numerous product initiatives, including a new lead-based model, last minute back up care, and automated tour scheduling for providers.
- Conducted technical and team-fit interviews for engineering candidates, playing a key role in building and maintaining a top-tier engineering team.
- Mentored engineers through code review, pairing, one-on-ones, and technical guidance, and was selected for a cross-departmental mentoring program.
- Led an infrastructure migration of large monolith applications from Heroku to AWS/K8S.
- Built and scaled SaaS solutions primarily in Ruby on Rails with PostgreSQL, Redis, Resque, and Solr; occasionally embedded with Go teams to pick up cross-stack work as needed.
- Architected and implemented numerous REST API integrations with external services (Google, Mapbox, Salesforce), plus GraphQL and gRPC interfaces.
- Scaled applications and optimized performance using Docker, Jenkins, Kubernetes, and AWS, actively monitoring and responding to high-traffic events to ensure a reliable user experience.
- Created a custom OmniAuth strategy gem for single sign-on integration.
- Ensured high quality code and architecture standards were maintained in a PCI-scoped application.
- Coordinated with Security Operations team to enhance application security.
- Maintained up-to-date application dependencies and tooling, proactively reducing security exposure across a PCI-scoped platform.
- Successfully upgraded the Rails framework versions without impacting production environments.
- Volunteered engineering skills to support civic engagement, building tools that help constituents discover and contact their elected officials across multiple channels including SMS, Facebook Messenger, and Twitter.
- Expanded platform capabilities to reach state-level officials and maintained backend delivery systems to ensure reliable constituent communication at scale.
- Developed and maintained a suite of Ruby on Rails internal business applications serving local unit and corporate staff across sales order management, customer service, single-copy route logistics, and retail partnership delivery operations.
- Stepped into an engineering leadership role during significant organizational restructuring, managing and integrating overseas contractor teams into existing workflows in the absence of a dedicated engineering manager.
- Led migrations of individual on-premises Linux applications to containerized Docker and Kubernetes environments on GCP as part of a company-wide cloud initiative, using Terraform for infrastructure provisioning and Helm for deployments.
- Led the development to implement Level 3 and CIT/MIT credit card processing in our Ruby on Rails credit card API, resulting in a substantial yearly savings by reducing processing fees.
- Independently designed and built a credit card tokenization application used by the sales team to securely process and bulk-input customer orders.
- Created a new API to interface with automated telephone attendant systems.
- Improved, debugged, and tested numerous existing applications across several infrastructure platforms, including Jenkins and Capistrano based deployments.
- Led rollouts of new software initiatives across a national network of 100+ local units, managing implementations independently or at the head of a team, with frequent cross-country travel spanning the full national footprint of Gannett properties.
- Directed 6-18 month business system conversions for newly acquired properties, migrating Circulation, Advertising, HR, and Finance operations into Gannett's proprietary platforms.
- Built trust with directors and VPs at newly acquired companies, several of whom were initially skeptical of the acquisition, to quickly learn their business and lead tailored software conversions.
- Developed and implemented custom software solutions to meet site-specific operational requirements.
- Served as the subject matter expert and final escalation point for a mission-critical Circulation software suite relied upon by 100+ daily newspaper locations — when critical processes such as day-close and financial period closures failed, all operations halted until resolved.
- Performed ad-hoc system updates and data corrections to restore operations when user-impacting issues arose, requiring deep knowledge of the underlying systems and data structures.
- Led internal projects to enhance support and helpdesk operations company-wide, including the implementation and administration of ServiceNow.
- Created and maintained a support knowledge base to expand self-service options and reduce escalation volume across the organization.
Lansing State Journal
Early Career
- iSeries Business Systems Analyst, Circulation Department Manager
skills
- Programming: Ruby/Rails, Python, Go, iSeries
- AI / LLM: OpenAI API, Anthropic API, Claude Code, GitHub Copilot, Ollama (self-hosted), LLM Integration, Prompt Engineering, RAG, Evals, Embeddings, Vector Search
- Database: PostgreSQL, Aurora, Redis/Valkey, MySQL, Solr, Sequel, SQLite
- Integrations: REST APIs, OmniAuth/SSO, Twilio, Stripe, GraphQL, gRPC, Mapbox
- Background Jobs: Sidekiq, Resque, Delayed Job, Shoryuken, SQS
- Automated Testing: Minitest, Selenium, Capybara, RSpec, Shoulda, Mocha, Webmock
- Frontend: HTML, JS, CSS, Hotwire, Stimulus, Turbo
- CI/CD & Version Control: Jenkins, CircleCI, GitHub Actions, GitHub, Bitbucket, Capistrano
- Observability: Splunk, SignalFX, Kibana
- Platform: AWS (EC2, EKS, IAM), GCP, K8S, Docker, Helm, Harness, Scalr, Heroku, Render, Terraform, VMs
education
- Lansing Community College, Electronics Engineering, Votech Honor Society President
references
- Upon Request