DevOps Engineer, Trilogy

Description:

You're the engineer who stabilizes 50+ SaaS products when no one else has the map. We need DevOps professionals capable of entering unknown AWS environments, restoring order, and driving uptime beyond 99.9% through rigorous monitoring, disciplined automation, and thorough root cause analysis. You'll break complex projects into single-day deliverables, deploy production-quality Python or JavaScript, and leverage AI as a force multiplier.

While most teams talk about "the cloud" and manually tend infrastructure, we're scaling reliability engineering across a portfolio of acquired products whose original creators have departed and whose documentation is incomplete. The challenge: you'll harness AI agents and contemporary tooling to explore unfamiliar systems 5–10x faster, document your findings, and automate defenses so recurring incidents become impossible. Rather than judging you on certifications and vendor badges, we'll observe how you troubleshoot under pressure, author a genuine 5-Whys analysis that identifies one preventable root cause, and construct automations that withstand production stress.

This isn't a tier-two "follow the runbook" position. Here, you author the runbooks, architect the deployment pipeline from development through staged rollouts to 10% and 100% with soak periods and rollback criteria, and implement the monitoring that detects corner cases. You challenge risky changes before execution. You distinguish infrastructure issues you own from application bugs Engineering owns, and you route permanent remediation to the correct team.

You'll operate at the engineering center of reliability, owning infrastructure initiatives, incident response with RCA, and change requests accompanied by copy-paste-ready runbooks. If you've already managed a significant SaaS platform and want to apply that expertise across a fleet, this is your opportunity. Bring advanced AWS knowledge, production-grade development skills, uncompromising scope discipline, and daily, mission-critical use of AI tooling. If you're prepared to maintain operational excellence, we want to hear from you.

What You Will Be Doing

• Leading complex infrastructure migrations, consolidations, production-level automations, and monitoring enhancements
• Responding to production outages, deploying immediate remediation, and drafting root cause analyses with permanent fixes delegated to accountable teams
• Authoring, reviewing, and executing production changes, including assessing whether a proposed change poses acceptable risk

What You Won’t Be Doing

• Spending your day in Jira and marathon status calls - we reward people who deliver solutions, not just document issues
• Preserving legacy systems forever - you'll be empowered to champion substantial upgrades
• Waiting on bureaucratic sign-off chains - you'll possess the authority to deploy immediate fixes during incidents

DevOps Engineer Key Responsibilities

• Advance reliability and standardization of cloud infrastructure across our expanding product portfolio by deploying comprehensive monitoring, automation, and AWS best practices.

Basic Requirements

• Deep AWS infrastructure expertise (this is our primary platform - other cloud experience alone won't cut it)
• Experience managing production infrastructure at a scale of hundreds of containers
• 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 CloudFormation)

About Trilogy

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 cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $50 USD/hour, which equates to $100,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.