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Trent Raber

Resume

I’ve been building software since 2005, mostly backend, mostly Ruby on Rails, with a long stretch of PHP and enough frontend and iOS to be dangerous. Since 2018 I’ve been managing engineers: hiring, process, architecture, and translating between the technical team and everyone else. I still write code.

Experience

GrailPay — Director of Engineering

August 2024 to present

  • Own technical design and architecture decisions, and the engineering process from intake through delivery, deployment, and operations.
  • Rebuilt the internal admin application in Rails, giving leadership and operations what they need for day-to-day support and automating enough of it to cut the support load on both ops and engineering.
  • Built a Rails app for engineering metrics: where time goes, and project and task completion rates by team and by person.
  • Revamped the external developer documentation platform.
  • Standardized documentation and project tracking from first concept through delivery.

Braintrust Tutors — Director of Engineering

May 2023 to August 2024

  • Led technical planning, requirements, and solution design across the product org.
  • Hired and onboarded developers, QA engineers, and product managers using the Who interview method.
  • Owned platform architecture documentation while still contributing to the codebase.
  • Represented engineering in InfoSec discussions with the New York City Board of Education.

LawnStarter — Engineering Manager

November 2021 to April 2023

  • Led the API team through an acquisition and the integration of the acquired company’s platform, including migrating hundreds of thousands of Stripe customer records.
  • Hired developers, QA engineers, and product managers (Who method again).
  • Built a quarterly engineering metrics approach that surfaced problem areas for the team and for individuals. That research fed into a paper by my VP of Engineering, Alberto Silveira: Engineering Productivity Goes Beyond “Just Code”.
  • Standardized how customer-facing Datadog metrics get documented.

RVshare — Engineering Manager

December 2019 to November 2021

  • Ran all engineering hiring for a stretch in 2021 and built the candidate tracking and evaluation process to do it.
  • Started sprint reporting on roadmap work versus defects versus engineering overhead (reviews, deployments, helping other developers).
  • Wrote the deployment process, and the documentation for it, that RVshare still uses.
  • Launched the company’s first real beta rollout, using Optimizely to ship a large feature to a selected group of users.

RVshare — Senior Software Developer

February 2019 to December 2019

  • Rails work on the API.
  • Led an initiative to standardize error handling, coding standards, peer review, and documentation, including an onboarding program for new engineers.

Dragonfly Research Group — Senior Software Developer

January 2018 to February 2019

  • Managed a small team of junior developers.
  • Built a boat-rental marketplace in PHP 7 (UX, frontend, and REST API design), an assessment platform for Eckerd College’s management training institute in Laravel using DDD, and a Facebook ad-campaign integration with an analytics dashboard on a Rails/React app.

Clear Idea Technology — Senior Software Developer

October 2005 to December 2017

  • Led teams of three to seven on PHP and Rails projects for twelve years.
  • Two years leading a team of four on a Rails backend, Angular frontend, and browser extension for an ad-tech startup.
  • Designed and built a Florida Keys tourism guide: PHP backend, REST services, and a native iOS app that delivered location-based deals.
  • Built the Rails backend and REST API for on-the-spot diamond pricing and quotes, and a PHP backend for a barcode-scanning app that identified cruelty-free products.

Other

  • Mentored youth teams at #SRQHacks in 2016 (special recognition) and 2017 (first place; the team was invited to speak at a Sarasota transportation symposium).

Tools

Ruby on Rails, PHP and Laravel, PostgreSQL and MySQL, JavaScript, React, Angular, REST API design, Objective-C and Swift.

Contact