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Steve ChesterSC
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Steve Chester

@stevechester

Principal Engineer at Obie who shipped a $200M insurance billing platform and AI tools.

United States
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At Obie, I designed and shipped an in-house insurance billing platform processing over $200M annually, with invoicing, double-entry ledgers, and carrier payouts. I also built an AI platform that resolves live-chat inquiries autonomously, reducing CSR chat volume by 47%.

I built a Slack assistant used daily by one-third of the company to query data and code, triage issues, and create pull requests. I also created a TypeScript SDK that lets partners sell Obie insurance within their products.

Before that, I built core applications and integrations at Industry Weapon, including a digital menu board management platform for Little Caesars that powers menu boards across 3,000+ restaurant locations. I also built customer-facing applications and a drag-and-drop design platform for digital signage.

At Aerick Media, LLC., I co-founded and built entertainment websites, publishing systems, and a community-driven music platform. My side projects include NeverWait, a scheduling and appointment management system, and Dottt, a menubar calendar app.

Experience

Work history, roles, and key accomplishments

Obie logoOB

Senior Software Engineer II

Obie

Feb 2021 - Jan 2023 (1 year 11 months)

As an early engineer, built core full-stack applications using React, TypeScript, Node.js, and GraphQL, establishing foundational capabilities across quoting, rating, underwriting, payments, and authentication. Built carrier integrations and versioned policy document pipelines, and established automated testing practices.

IW

Engineering Manager - Applications

Industry Weapon

Apr 2019 - Feb 2021 (1 year 10 months)

Led a team of application engineers while contributing as a senior individual contributor. Built core applications and integrations for the company's CMS platform, including a digital menu board management platform for Little Caesars powering 3,000+ locations.

IW

Software Engineer

Industry Weapon

Jun 2016 - Apr 2019 (2 years 10 months)

Served as Team Lead for the Applications team, mentoring engineers and acting as a cross-team technical resource. Architected and built several complex customer-facing applications, including content management systems, interactive touchscreen kiosks, and a drag-and-drop design platform.

AL

Co-Founder & Software Engineer

Aerick Media, LLC.

May 2011 - May 2016 (5 years)

Co-founded and built a portfolio of entertainment websites, developing content aggregation and publishing systems. Designed and built a community-driven music platform and built SEO and advertising automations to support audience growth.

Education

Degrees, certifications, and relevant coursework

PI

Pittsburgh Technical Institute

Associate of Science, Information Technology

2007 - 2009

Associate of Science Degree in Information Technology with a concentration in Network Administration.

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