Jon Kinney is a seasoned technology leader and Partner & CTO with 16+ years building web and mobile products, currently shaping client-facing software at Headway. He specializes in architecting modern full-stack Rails applications and pairing engineering with product strategy to drive acquisition and retention for startups and corporate innovation teams. Jon has run engineering teams, taught and spoken at conferences, and previously served as CTO and Chief Architect at early-stage companies where he guided product pivots and fundraising-readiness. An active open-source contributor, his work includes practical improvements to widely used Ruby tooling such as CanCanCan and a DocuSign API wrapper that added OAuth2 and multi-document support. Based in De Pere, Wisconsin, he brings a hands-on blend of backend expertise, developer tooling, and client collaboration that helps teams ship thoughtful, user-driven software.
16 years of coding experience
9 years of employment as a software developer
Bachelor of Business Administration Management Information Systems, Bachelor of Business Administration Management Information Systems at University of Wisconsin-Eau Claire
Contributions:107 commits, 3 PRs, 4 pushes in 4 years 3 months
Contributions summary:Jon primarily contributed to the DocuSign REST API wrapper gem by adding features and improving existing functionality. Their contributions included implementing multi-document uploading, supporting file input/output streams, and adding methods for template creation and management, alongside related documentation and example requests. Furthermore, they modified the gem's internal architecture to facilitate OAuth2 authentication. These changes enhanced the gem's capabilities for interacting with the DocuSign API, including new functions for embedded signing and general API features.
Sublime Text 2 plugin for running ruby tests! (Unit, RSpec, Cucumber)
Role in this project:
Backend Developer & Test Automation Engineer
Contributions:26 commits in 7 days
Contributions summary:Jon primarily worked on enhancing a Sublime Text 2 plugin designed for running Ruby tests. Their contributions focused on refining the plugin's ability to parse and display test results, specifically for RSpec and Cucumber. The user implemented more robust error and pending detection within test output, including the addition of new failure matchers to improve the plugin's ability to correctly report on the status of tests. These changes involved modifying regular expressions to identify various failure scenarios.
rspec-cucumberrubyunitrspecsublime
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