russell.ballestrini.net/content/pages/cover-letters/2025-11-04-automattic-senior-systems-engineer-russell-ballestrini.rst

Automattic - Senior Systems Engineer
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:date: 2025-11-04

To Automattic:

firstly, my tumblr!

* https://unturf.tumblr.com/

I have over 15 years of systems infrastructure & scaling experience applicable to a Senior Systems Engineer role at Automattic. At Remind (2017-2020), I managed AWS infrastructure for 60+ Ubuntu microservices running on ECS, ensuring critical services scaled during COVID-19 lockdowns supporting millions of teachers & students. I introduced Datadog with EC2 agents for container APM, logs, & custom metrics—establishing monitoring & alerting strategies that maximized uptime & reduced incident response times. Nginx proficiency spans reverse proxy configurations, load balancing, & SSL termination across production environments. MySQL/MariaDB experience includes schema design, query optimization, replication strategies, & managing databases at scale. PHP expertise dates back to early career work—including maintaining a WordPress plugin for LinkPeek (my first bootstrapped startup) that took screenshots from WordPress pages & posts of remote links. russell.ballestrini.net originally launched on WordPress before migrating to Pelican static site generator, giving me hands-on experience with WordPress ecosystem challenges & workflows.

Can you believe that over 42% of the Internet is STILL powered by WordPress!

Infrastructure-as-code proficiency spans CloudFormation, Terraform, Ansible, & SaltStack. At Coursemojo (2022-2025), I designed CI/CD pipelines for two monolithic services using GitHub Actions & Docker ECS, scaling AI-powered educational tools while maintaining security & reliability. Configuration management experience includes fleet orchestration, automated deployments, & self-healing systems. Strong Python, Bash, & PHP skills enable writing automation scripts, infrastructure tooling, & debugging production issues efficiently. Founded & open-sourced multiple SaaS platforms (Remarkbox privacy-focused commenting, Make Post Sell commission-free e-commerce) demonstrating commitment to transparent, maintainable systems—values that align with Automattic's open source philosophy. The ability to autonomously architect solutions, attention to detail, & focus on developer productivity mirror my career approach.

Automattic's mission to democratize publishing & make web a better place resonates deeply. WordPress powers a significant portion of the web & the opportunity to support developers shipping software at that scale would be incredibly fulfilling. Building reliable, performant infrastructure that enables millions of sites to thrive combines my infrastructure expertise with meaningful impact. I'm comfortable with the 2-3 weeks/year travel requirement for in-person team meetings & excited about working with a distributed, global team. I'd love to apply my systems engineering experience, WordPress ecosystem knowledge, & uptime-focused mindset to help Automattic maximize service availability, optimize performance, & maintain security across its infrastructure.

Russell Ballestrini

FOSS portfolio: https://www.unturf.com/software