Jason L Cachia
Engineering Leader
(941) 202-3922 | North Port, Florida
education
Lansing Community College
Electronics Engineering
Votech Honor Society President
leadership & management
- Directly managed a department of 15+ employees across the full people-management lifecycle: recruiting, interviewing, hiring, performance appraisals, compensation, and budget ownership.
- Covered the engineering-manager function for two teams (around 10 engineers) at Care.com during parental leaves, including a stretch running both concurrently, owning 1:1s, performance management, and a formal Performance Improvement Plan through to resolution. Was encouraged toward a full-time Engineering Manager role.
- Covered day-to-day engineering leadership, including integration and direction of an overseas contractor team, when an Engineering Manager departed without backfill.
- Selected for a cross-departmental mentoring program and served as a primary technical and team-fit interviewer across multiple roles.
work experience
Hands-on engineering leader with 9+ years building production Ruby on Rails systems and 20 years in technology, pairing deep Rails and LLM-integration work with a track record of leading engineering teams and contractors, onshore and offshore, to ship and scale reliable products.
- 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.
- 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.
- Designed and managed integrations with OpenAI and Anthropic APIs to generate personalized insights and reflections from user journal 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.
- Architected and developed the application using Ruby on Rails, Hotwire, and Stimulus, delivering a modern, responsive user experience.
- 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.
- Authored and maintained the CI/CD pipeline from scratch using GitHub Actions, ensuring automated testing and reliable deployments.
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.
- Covered the engineering-manager function for two teams across their managers' parental leaves, including a period covering both concurrently, owning 1:1s, performance management, and delivery
- Ran a formal Performance Improvement Plan for an engineer, including documentation, coaching, and milestone tracking to resolution.
- Selected for a cross-departmental mentoring program in addition to ongoing mentorship within my own team.
- Served as a primary technical and team-fit interviewer throughout tenure, shaping hiring standards and building a top-tier engineering team.
- Encouraged by leadership toward a full-time Engineering Manager role.
- 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.
- Maintained and supported the platform's existing Stripe integration, handling both customer payments and caregiver payouts across the marketplace.
- 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.
- Led an infrastructure migration of large monolith applications from Heroku to AWS/K8S.
- Coordinated with Security Operations team to enhance application security and maintain code and architecture standards in a PCI-scoped application.
- 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.
- 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.
- Covered day-to-day engineering leadership and delivery ownership as an individual contributor when the Engineering Manager departed and was not backfilled, including direction and integration of an overseas software development team, during a period of significant organizational restructuring.
- Developed and maintained a suite of Ruby on Rails internal business applications serving local units and corporate staff across sales order management, customer service, single-copy route logistics, and retail partnership delivery operations.
- 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 rollouts of new software initiatives across a national network of 100+ local units, managing implementations independently or as the leader 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.
- 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.
- Led internal projects to enhance support and helpdesk operations company-wide, including the implementation and administration of ServiceNow.
- Supervised a team of Computer Operators responsible for executing the daily close process and distributing operational reports throughout the organization.
- Delivered training to users at all levels on business systems and processes.
- Provided local and regional support for custom programming and reporting on an iSeries system.
- Directly managed a Circulation Service Department of 15+ employees, overseeing inbound and outbound call center, front desk, and customer retention operations.
- Owned the full people-management lifecycle for the department: recruiting, interviewing, hiring, performance appraisals, compensation, and PIPs, plus payroll and non-payroll budget ownership.
- Led initiatives to drive sales growth and improve customer satisfaction across the department.
- Managed a contractor force responsible for daily newspaper delivery to residences and businesses across the district, 365 days a year.
- Recruited, trained, and motivated contractors to maintain exceptional delivery service standards.
skills
- Leadership & Management: Performance Management, Hiring & Interviewing, Budget Ownership, Coaching & Mentorship, Cross-team Leadership
- Payments & Billing: Stripe (subscriptions, billing API, marketplace payouts, account reconciliation), Level 3/CIT-MIT credit card processing, credit card tokenization, PCI-scoped development
- 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
- Integrations: REST APIs, OmniAuth/SSO, Twilio, Stripe, GraphQL, gRPC, Mapbox
- Platform: AWS, GCP, Kubernetes (K8S), Docker, Helm, Harness, Scalr, Heroku, Render, Terraform, VMs
- Database: PostgreSQL, Redis/Valkey, MySQL, Solr, Sequel, SQLite
- CI/CD & Version Control: Jenkins, CircleCI, GitHub Actions, GitHub, Bitbucket, Capistrano
- Automated Testing: Minitest, Selenium, Capybara, RSpec, Shoulda, Mocha, Webmock
education
- Lansing Community College, Electronics Engineering, Votech Honor Society President
references
- Upon Request