Senior DevOps Engineer, Trilogy (Remote) - $100,000/year USD

About This Role

You're the engineer who maintains uptime across 50+ SaaS products when nobody else knows where to start. We need DevOps engineers capable of exploring unknown AWS environments, restoring order from disorder, and driving availability above 99.9% through genuine monitoring, automation, and root cause analysis. You'll break down complex projects into single-day tasks, deliver production-ready Python or JavaScript, and leverage AI as your assistant.

Most organizations claim "cloud expertise" while manually tending servers. We're systematizing reliability across dozens of acquired products where the original builders have departed and the documentation is incomplete. That's the challenge: you'll employ agents and current tooling to understand new systems 5–10x more quickly, document your findings, and automate solutions so the same incident never recurs. Rather than judging you on certifications and vendor badges, we'll observe you troubleshoot in real time, produce an actual 5-Whys that identifies one preventable root cause, and construct automations that withstand production conditions.

This is not an L2 "follow the runbook" position. Here, you author the runbooks, architect the deployment from dev through staged through 10% to 100% with soak periods and rollback criteria, and create the monitors that detect edge cases. You reject risky changes before execution. You distinguish infrastructure failures you control from application bugs Engineering controls, and you route permanent remediation to the correct team.

You'll operate at the engineering center of reliability, managing infrastructure initiatives, incident response with RCAs, and change requests accompanied by copy-paste-executable instructions. If you've already managed a significant SaaS product and want to expand that discipline across a portfolio, join us. Bring expert-level AWS knowledge, production-grade development skills, strict scope discipline, and daily, essential use of AI tools. If you're prepared to maintain operational stability, please apply.

What You Will Be Doing

• Executing complex infrastructure migrations, consolidations, production-grade automations, and monitoring modifications
• Investigating production outages, deploying immediate remediation, and documenting root cause analyses with permanent fixes routed to the accountable teams
• Authoring, reviewing, and deploying changes into production, including assessing whether a proposed change is safe to deploy

What You Won’t Be Doing

• Spending time in Jira and continuous status meetings - we prioritize people who can deliver solutions, not merely document problems
• Preserving legacy systems forever - you'll be authorized to pursue substantial improvements
• Waiting for bureaucratic approval processes - you'll possess the authority to deploy immediate fixes during incidents

Senior DevOps Engineer Key Responsibilities

• Advance reliability and standardization of cloud infrastructure across our expanding product portfolio by deploying robust 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.

Crossover Job Code: LJ-5236-AE-COUNTRY-SeniorDevOpsEn.002