James Gifford

Director of Engineering

Columbus, Ohio, United States14 yrs 2 mos experience

Most Likely To SwitchHighly Stable

Key Highlights

Expert in CI/CD and release management.
Led development of high-performance e-commerce platforms.
Strong background in Ruby on Rails and web applications.

Stackforce AI infers this person is a Backend-heavy Fullstack Engineer with expertise in E-commerce and CI/CD practices.

Contact

Skills

Core Skills

Ci/cdRelease ManagementRuby On RailsE-commerce Development

Other Skills

Operational Best PracticesSoftware DeploymentJenkinsRelease EngineeringGitHubRSpecElasticsearchPHPMySQLPostgreSQLSidekiqShell ScriptingTest Driven DevelopmentLinux System AdministrationSoftware Development

About

As a Principal Software Engineer at Upstart, I lead the releases, pipeline development, and deployments of a large Ruby on Rails monolith, ensure pipeline stability and supporting cultural shifts to move to a true CI/CD world. I have over four years of experience at Upstart, where I also worked on the Developer Experience and Investor teams, leading cross-functional initiatives for site and database performance and platform-level improvements for tooling. I have experience developing web applications for various fields, including marketplaces and e-commerce. I enjoy solving complex problems with a holistic and user-centric approach, and I strive to deliver high-quality software solutions that make a positive impact.

Experience

14 yrs 2 mos

Total Experience

4 yrs 6 mos

Average Tenure

7 yrs 1 mo

Current Experience

Upstart

5 roles

Director of Engineering

Promoted

Oct 2025 – Present · 7 mos

At Upstart, I lead the investments in our CI/CD infrastructure, focusing on operationalizing best practices for both the monolith and for our microservices.

CI/CDRelease ManagementOperational Best Practices

Distinguished Software Engineer

Aug 2024 – Dec 2025 · 1 yr 4 mos

Principal Software Engineer

Promoted

Aug 2022 – Jul 2024 · 1 yr 11 mos

January 2023-Present: Managing releases, pipelines and deployments of a large Ruby on Rails Monolith. Focused on pipeline stability and supporting cultural shifts to move to a true CI/CD world.

Release ManagementSoftware DeploymentJenkinsRelease EngineeringRuby on RailsGitHub+1

Senior Software Engineer

Aug 2020 – Aug 2022 · 2 yrs

July 2021-January 2023: Developer Experience team. Managing cross functional initiatives for site and database performance and platform level improvements for tooling.
August 2020-June 2021: Investor Team

GitHub

Software Engineer

Mar 2019 – Aug 2020 · 1 yr 5 mos

GitHub

Rvshare

Software Technical Lead

Jan 2017 – Mar 2019 · 2 yrs 2 mos · Akron, Ohio

My job as tech lead was to continue to write code (Ruby on Rails, Elasticsearch, PHP and MySQL), but with the added responsibilities of representing the team to management (I reported directly to the VP of Engineering), vetting our plans for feature delivery, dealing with many of the details of our project management process, as well as assisting with the departments technical roadmap. These include things such as:
Establishing common technical vision for the projects and applications
Collaborating with product stakeholders on scope
Collaborating with QA leadership and teams to help ensure quality of work
Assisting product owners with technical product requirements
Technical architecture and design
Working with knowledge experts on the technical details of features
Leading daily stand ups and weekly sprint plannings
Representing the team to management from a technical perspective as well as representing management to the team for most day-to-day operations

Ruby on RailsElasticsearchPHPMySQL

Hotcards

Lead Software Developer

Jul 2014 – Jan 2017 · 2 yrs 6 mos · Cleveland/Akron, Ohio Area

Lead Developer:
Lead the development of a custom-built ecommerce platform for the commercial printing industry.
Stack:
Ruby on Rails
PostgreSQL
Sidekiq
Elasticsearch
Projects:
Refactoring complex logic to be thread safe
Creating automated deployment tool chain (deploys were by hand previously)
Leading rewrite of application to be mobile-friendly and improve performance 5x.
Responsibilities include:
Writing code to solve business problems
Ensuring code quality via code review
Finding and managing contractors
Selecting vendors and technologies that suit our needs
Business requirement gathering for features
Coordinating with other departments internally for prioritizing features and bug fixes
Leading an Agile team using a variant of Kanban
DevOps:
Tools used include:
Ubuntu Server
Configuration Managment (Ansible)
Monitoring and Alerting Toolchain (Splunk, AppSignal, Errbit, Graphite/StatsD)
Amazon Web Services (S3, EC2, RDS, VPC)
Projects include:
Implementing backups
Implementing and testing disaster recovery
Bringing platform uptime to 99.99%
Bringing infrastructure under configuration management (Ansible)

Ruby on RailsPostgreSQLSidekiqElasticsearchGitHubE-commerce Development

Dragonid, llc

Engineer

Aug 2013 – Jul 2014 · 11 mos · Cleveland/Akron, Ohio Area

Software Developer for a Biomedical company. Along the way assisted with a full-stack (C#/Windows, Django/Linux) software development project which has been deployed at several major Cleveland Universities.

Snowy penguin solutions, llc

Consultant

Jan 2013 – Jan 2019 · 6 yrs · Greater Cleveland

Software Development consultancy. Company for side projects to go through.

Launchhouse

Manager of IT & Special Projects

Sep 2012 – Feb 2018 · 5 yrs 5 mos · Shaker Heights

Ubuntu

Ask Ubuntu Community Elected Moderator

Feb 2012 – Nov 2019 · 7 yrs 9 mos

Boy scouts of america: greater cleveland council

Outdoor Skills Instructor

Jun 2011 – Aug 2011 · 2 mos · Rock Creek Ohio

Outdoor Skills instructor. Responsibilities included running the Wilderness Survival Outpost each week, and teaching various Outdoor Skills Merit Badges.