CHIP CRESSMAN Director of Engineering · Seattle, WA Email: hello@chipcressman.com Website: https://chipcressman.com LinkedIn: https://www.linkedin.com/in/cressmancm/ GitHub: https://github.com/cressmancm Résumé (PDF): https://chipcressman.com/chip-cressman-resume.pdf SUMMARY Director of Engineering with 15+ years in software, specializing in building high-performing engineering teams that ship high-quality code predictably. Spent nearly 10 years at Skilljar, growing with the company from an early-stage startup through its acquisition by Gainsight. Joined as the first frontend engineer and rose to Director of Engineering, leading up to 30 engineers across 5 teams in the US and Poland. Scaled the team by hiring 20+ engineers and developing a management team from both experienced hires and internal promotions. Moved the org from quarterly releases and year-long projects to planning and delivering in 6-week cycles, regularly completing 80%+ of the initiatives teams committed to each cycle while holding 99.95% uptime. Built an AI-native engineering organization, moving production code written by AI from 0% to 90%+. Leads with transparency and empathy, setting up operating rhythms that managers and engineers own and run. Partners closely with founders and technical leaders to give teams one shared direction to deliver on. EXPERIENCE Skilljar by Gainsight · Sep 2016 – Jul 2026 Customer education platform; acquired by Gainsight in April 2025. Director of Engineering, Education Engineering · Apr 2025 – Jul 2026 - Led up to 30 engineers across 5 teams in the US and Poland, with product and design partners for each team. - After the acquisition, took ownership of Northpass, a customer education platform similar to Skilljar, and its 2 teams in Poland, then restructured the combined organization around the highest business priorities. - Oversaw onboarding of the largest customer in Skilljar's history, running a cross-functional tiger team and scaling the platform for 1M+ monthly active learners, including cutting key dashboard load times by up to 72%. - In partnership with Product, rolled out and refined 6-week planning cycles, so new priorities waited at most one cycle to start, and teams rarely had to drop in-flight work when priorities changed. Teams regularly completed 80%+ of the initiatives they committed to each cycle. Co-hosted R&D all-hands every cycle with the Director of Product to keep teams informed, aligned, and focused. - Set the org's vision in an annual technology plan, with north-star goals and the metrics to track them. - Cut deploy times by about 40% as deploys grew to 100+ a month, while holding S1/S2 incidents to fewer than 3 a month and uptime at 99.95%. - Built an AI-native engineering organization, moving production code written by AI from 0% to 90%+. Personally authored many AI agents, including one that proactively triaged security alerts and another that re-prioritized the escalation backlog daily. Senior Engineering Manager · Feb 2022 – Apr 2025 Engineering Manager · Jul 2019 – Feb 2022 Senior Frontend Engineer Lead · Dec 2018 – Jul 2019 Senior Frontend Engineer · Dec 2017 – Dec 2018 Frontend Engineer · Sep 2016 – Dec 2017 EARLIER EXPERIENCE Lead Engineer (contract), GYST · Jan 2016 – Sep 2016 - Brought in by the founders as the sole engineer of an estate-planning startup, owning everything technical: development, hosting, deployments, email, third-party integrations, security, and maintenance. - Took the alpha MVP to a production e-commerce site, with a custom CMS that let the team publish content, manage ads and user accounts, and run the online store on their own (Rails, Heroku, Stripe, AWS S3). Freelance Full Stack Developer, Cressman Consulting · Jan 2016 – Sep 2016 - Built a press-launch landing page for Visual Vocal, an augmented-reality startup for architects, working with the creative firm Tectonic. - Built a WordPress site for a local real estate agent with content tools and a step-by-step guide so his team could run it. Frontend Developer, Glympse · Oct 2013 – Jan 2016 - Built Experience Map, a self-serve tool that let internal teams, partners, and end users customize map styles and behavior to fit their brand. - Automated email templates with Gulp and npm tooling for building, testing, and deploying, cutting new-email build time to minutes. - Shipped a new interactive homepage under a strict 2-week deadline, from design through deployment, ahead of new product announcements. Full Stack Developer, Moby Inc · Jul 2012 – Sep 2013 - One of 2 developers at a web and mobile agency, architecting, building, and maintaining web and mobile apps for a range of clients, with a focus on responsive design and fast load times. - Built iconmobile's homepage, personalized to each visitor's location, time, and weather, and extended OrangeRuler, a Rails school-fundraising platform, with time-zone support, corporate donation matching, and new prize models. - Shipped a blackjack game in DoubleDown Casino's iOS and Android apps, working with the client's product, design, and QA teams. Backend Developer, VML (WPP) · Aug 2010 – Jul 2012 - Developed .NET web apps for Microsoft, Crocs, T-Mobile, and Dell, including the award-winning Gears of War 3 rewards site and the Crocs global redesign. INDEPENDENT WORK Kept · https://github.com/cressmancm/KeptApp · 2026 - Free, open-source macOS menu bar app that backs up an Apple Photos library to a NAS on a schedule, so 30 years of photos don't live only in iCloud. - An experiment in AI-native development and a first Mac app, built with an AI coding agent as a pair programmer to learn firsthand where AI speeds engineers up and where it still needs human judgment. - Some of those photos, if you're curious: https://chipcressman.photo SKILLS - Leadership: org design and scaling, hiring and talent development, post-acquisition integration, distributed teams, cross-functional partnership - Delivery: DORA and engineering metrics, 6-week planning cycles, incident management, platform reliability, AI-assisted development - Technical: Python, Django, AWS, CI/CD, Ruby on Rails, HTML, CSS, JavaScript, and frontend architecture EDUCATION B.S., Computer Information Systems, Grove City College · 2010