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

About This Role

You're the engineer who maintains uptime for 50+ SaaS products while others are still figuring things out. We need DevOps engineers who can step into unknown AWS environments, restore order from disorder, and drive availability beyond 99.9% through genuine monitoring, genuine automation, and genuine root cause analysis. You'll break down complex projects into single-day increments, deliver production-ready Python or JavaScript, and leverage AI as your assistant.

Most organizations talk about "cloud" while manually tending servers. We're building industrial-scale reliability across dozens of acquired products where the founding engineers have departed and the documentation is incomplete. That's where it gets interesting: you'll employ agents and contemporary tools to understand unfamiliar systems 5–10x faster, 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 a tier-2 "follow the runbook" position. In this capacity, you author the runbooks, architect the deployment from development to staging to 10% to full rollout with soak periods and rollback conditions, and create the monitors that detect corner cases. You block risky changes before someone executes them. You distinguish infrastructure failures you control from application bugs Engineering controls, and you route permanent remediation to the appropriate team.

You'll operate at the engineering center of reliability, taking ownership of infrastructure initiatives, incident management and root cause analyses, and change requests accompanied by copy-paste-executable runbooks. If you've previously owned a substantial SaaS product and wish to apply that expertise to an entire fleet, join us. Bring expert AWS knowledge, production-quality coding ability, disciplined scope management, and daily, essential use of AI tooling. If you're prepared to maintain operational continuity, please apply.

What You Will Be Doing

• Advanced infrastructure migrations, consolidations, production-quality automations, monitoring modifications
• Diagnosing production incidents, deploying immediate remediation, and authoring root cause analyses with permanent solutions assigned to responsible teams
• Designing, reviewing, and implementing production changes, including assessing whether a proposed change is safe to deploy

What You Won’t Be Doing

• Spending your time in Jira and continuous status meetings - we value individuals who can deliver solutions, not simply 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 to address incidents

Senior DevOps Engineer Key Responsibilities

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

Basic Requirements

• Extensive AWS infrastructure expertise (this is our core platform - experience with other clouds alone won't suffice)
• Track record owning substantial production infrastructure and resolving production outages autonomously (not merely executing a runbook)
• Track record scripting with Python and Bash for routine administrative operations
• Track record managing and migrating production databases across multiple engines (including MySql, Postgres, Oracle, MS-SQL)
• Track record with infrastructure automation (Terraform, Ansible, or CloudFormation)
• Linux systems administration expertise

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-Dubai-SeniorDevOpsEn.016