Open to opportunities

Kevin Wynn

@kevinwynn

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Senior full-stack software engineer building cloud-native billing and SRE systems.

United States

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What I'm looking for

I’m looking for a role where I can build reliable, cloud-native systems end-to-end—frontend, backend, and DevOps—owning architecture, CI/CD, and production operations with modern TypeScript, Kubernetes, and infrastructure automation.

I’m a Senior full stack software engineer with over 15 years of professional experience spanning frontend, backend, devops, and infrastructure roles. I bring strong ownership of end-to-end product delivery—from architecture decisions to production-grade operations.

At Cloudflare, I led design and implementation for a subscriptions management system that let customers upgrade, downgrade, or change subscription details. I also implemented a drift management and translation layer to keep data consistent between Cloudflare’s database and 3rd-party payment processing systems, and designed a failover manager to keep billing platforms operational during data center outages.

I’ve modernized delivery pipelines and rebuilt key product experiences. I converted ci/cd pipelines from Teamcity to Gitlab ci/cd, implemented argo canary rollouts, and rebuilt blog.cloudflare.com using Astrojs + React as a server-rendered site deployed with Cloudflare Pages.

Earlier, at StarshipHSA and YouEarnedIt/Kazoo, I worked across infrastructure and SRE—standing up Kubernetes (AWS EKS) with Helm and automating ci/cd pipelines, plus leading architecture to merge systems into a single GCP Kubernetes cluster. I’m excited by work that blends engineering rigor with reliability at scale.

Experience

Work history, roles, and key accomplishments

Senior Systems Engineer

Cloudflare

Jul 2021 - May 2026 (4 years 10 months)

Led design and implementation of a subscriptions management system that enabled customers to upgrade, downgrade, or change subscription details. Built billing platform resilience with drift/translation between Cloudflare and payment systems, a failover manager for data center outages, and migrated CI/CD pipelines while rebuilding blog.cloudflare.com with AstroJS and React.

TypeScript Astro React Kubernetes Helm CI CD Terraform Postgres

Senior Software Engineer

StarshipHSA

Jul 2020 - Jul 2021 (1 year)

Implemented Kubernetes-based infrastructure using AWS EKS and Helm, and set up automated CI/CD pipelines for builds and deployments. Built React Native onboarding flows and an investing platform that lets customers invest HSA funds into stock options.

TypeScript React Native Prisma PostgreSQL Kubernetes Helm GitHub Actions Terraform

Senior Software Engineer

YouEarnedIt/Kazoo

Sep 2018 - Jul 2020 (1 year 10 months)

Led and simplified engineering decisions to merge two companies by unifying Heroku and AWS systems into a single GCP Kubernetes cluster. Implemented CI/CD infrastructure to support the merged environment.

TypeScript Ruby on Rails MongoDB GCP Kubernetes Helm CircleCi Spinnaker Terraform

Software Engineer

HomeAdvisor

Nov 2017 - Sep 2018 (10 months)

Implemented a new React-based framework and rearchitected the customer interview flow. Worked across frontend and backend technologies including TypeScript, Java, and MySQL.

TypeScript React Java MySQL Frontend Development Interview Flows

Software Engineer

OutboundEngine

Apr 2014 - Nov 2017 (3 years 7 months)

Built frontend applications that enabled customers to create dynamic landing pages based on profile details. Developed with JavaScript and Java services backed by MySQL.

JavaScript Java MySQL Frontend Development

Software Engineer

Atomic Design and Consulting

Jan 2013 - Apr 2014 (1 year 3 months)

Developed software using WordPress and PHP to support web projects and maintenance needs. Applied engineering best practices to deliver reliable updates for client sites.

WordPress PHP Web Development Backend Development Content Management