Senior DevOps Engineer, Trilogy; Remote

You're the engineer who maintains uptime across 50+ SaaS products when others are still figuring it out. We need Dev Ops engineers capable of exploring unknown AWS environments, bringing order to disorder, and driving availability beyond 99.9% through genuine monitoring, automation, and root cause analysis. You'll break down complex projects into daily deliverables, deliver production-ready Python or JavaScript, and leverage AI as your assistant.

While most organizations talk about "the cloud" while hand-holding individual servers, we're systematizing reliability across dozens of acquired solutions where the original developers are gone and the documentation is incomplete. The challenge: you'll leverage agents and contemporary tools to understand unfamiliar systems 5–10x faster, document your findings, and automate solutions so recurring incidents become impossible. Rather than judging you on certifications and buzzwords, we'll observe you troubleshooting in real time, producing a genuine 5-Whys analysis that identifies a single preventable root cause, and creating automations that withstand production conditions.

This isn't an L2 "follow the instructions" position. In this role, you author the procedures, architect the deployment from development through staging to 10% then 100% with soak periods and rollback conditions, and create the monitoring that detects corner cases. You block risky changes before they reach production. You distinguish infrastructure failures you're responsible for from application bugs Engineering must address, and you route permanent solutions to the appropriate team.

You'll occupy the engineering heart of reliability, managing infrastructure initiatives, incident resolution and RCAs, and change requests complete with executable runbooks. If you've previously owned a significant SaaS platform and want to expand that practice across an entire fleet, join us. Bring advanced AWS knowledge, production-quality development skills, strict scope discipline, and daily, essential use of AI tooling. If you're prepared to maintain operational excellence, please apply.

• Sophisticated infrastructure migrations, consolidations, production-quality automations, monitoring implementations
• Investigating production incidents, deploying immediate remediation, and producing root cause analyses with permanent solutions routed to responsible teams
• Authoring, validating, and deploying production changes, including assessing whether a proposed modification is safe to implement

• Spending time in Jira and continuous status meetings - we reward people who deliver solutions, not those who merely document problems
• Supporting legacy systems forever - you'll be authorized to implement substantial improvements
• Waiting on bureaucratic approval processes - you'll possess the authority to deploy immediate remediation during incidents

• Drive reliability and standardization of cloud infrastructure across our growing product portfolio by implementing robust monitoring, automation, and AWS best practices.

• Deep AWS infrastructure expertise (this is our primary platform - other cloud experience alone won't cut it)
• Experience owning large production infrastructure and troubleshooting production outages independently (not just following a runbook)
• Experience scripting with Python and Bash for day-to-day administration operations
• Experience managing and migrating production databases with multiple engines (including MySql, Postgres, Oracle, MS-SQL)
• Experience with infrastructure automation (Terraform, Ansible, or Cloud Formation)
• Linux systems administration expertise

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things:
Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern…