russell.ballestrini.net/content/pages/cover-letters/2026-01-17-prompt-health-senior-devops-engineer-russell-ballestrini.rst

Prompt Health - Senior DevOps Engineer
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:date: 2026-01-17
:status: draft

To the Prompt Health team:

Healthcare software that actually works means clinicians spend time with patients instead of fighting their tools. At $100M+ ARR growing 100%+ YoY, you've proven the product works. Now you need infrastructure that scales with that growth without breaking. That's what I do.

**Datadog & observability**: At Remind, I introduced Datadog with EC2 agents for container APM, logs, & custom metrics across 60+ microservices supporting 30M users. At Coursemojo, I did it again with Fargate sidecar agents. I know how to instrument systems so engineers can debug production issues fast instead of spending hours correlating logs across services.

**Kubernetes & container orchestration**: ECS/EKS deployments throughout my career. At Remind, I managed the container infrastructure that kept critical education services running during COVID-19 lockdowns when usage spiked dramatically. Currently building unsandbox.com, a multi-tenant remote code execution platform with container orchestration, user isolation, & resource quotas across 42+ programming languages.

**Terraform & infrastructure-as-code**: CloudFormation, Terraform, Ansible, SaltStack. At Cofense (2020-2022), worked in security-focused environments (SOC2/FedRAMP) where infrastructure needed to be reproducible, auditable, & secure by default. Healthcare compliance requirements aren't new territory.

**AWS at depth**: EC2, ECS, RDS, DynamoDB, SQS, Lambda, CloudFormation. Built infrastructure handling millions of concurrent users that needed to be both cost-effective & reliable. At Remind, I led cloud cost optimization initiatives while maintaining the reliability 30M users depended on.

The combination of fast growth, healthcare impact, & serious infrastructure challenges is exactly what I'm looking for.

Russell Ballestrini

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