russell.ballestrini.net/content/pages/cover-letters/2026-01-05-trunk-tech-lead-russell-ballestrini.rst

Trunk - Tech Lead / Senior Platform Engineer
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:date: 2026-01-05

.. Skipped - SF hybrid only

To Trunk:

Flaky tests & broken CI have stolen more engineering hours from my teams than any other single problem. At Remind, I watched talented engineers lose entire afternoons to "it works on my machine" mysteries while our test suite flickered between green & red for reasons nobody could explain. The problem you're solving is real & I've felt it deeply.

At Coursemojo (2022-2025), I designed CI/CD pipelines using GitHub Actions & Docker for two monolithic services. Built the infrastructure that let a small team ship AI-powered educational tools reliably. The challenge wasn't writing the pipelines; it was maintaining confidence in them as the codebase grew. Every flaky test eroded trust, & eventually engineers started ignoring failures. That's the death spiral Trunk prevents.

My infrastructure experience spans 15+ years: AWS (ECS, EC2, RDS, DynamoDB, CloudFormation), containerization & orchestration, Python & TypeScript, data pipelines, & observability (introduced Datadog at Remind for container APM across 60+ microservices). At Cofense (2020-2022), I worked in security-focused environments where CI/CD reliability wasn't optional. SOC2/FedRAMP compliance meant every deployment needed to be auditable & reproducible.

The Platform/Data Engineering focus resonates strongly. Building data ingestion pipelines that handle real-time & batch data from CI systems is the kind of problem I enjoy: high throughput, diverse sources, & direct impact on developer experience. I've built similar pipelines for log aggregation, metrics collection, & event processing.

Trunk's backing (a16z, founders from Uber/Google/YouTube) & mission to treat developer experience as mission-critical infrastructure aligns with how I've approached my career. The best infrastructure is invisible. Engineers should be thinking about their product, not their tools. I'd love to help build that.

Russell Ballestrini

https://russell.ballestrini.net | https://github.com/russellballestrini