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

About the Role

You're the engineer who sustains 50+ SaaS products when nobody else has the answers. We need DevOps engineers capable of exploring unknown AWS environments, stabilizing disorder, and driving uptime beyond 99.9% through genuine monitoring, genuine automation, and genuine RCAs. You'll break complex projects into one-day increments, deliver production-ready Python or JavaScript, and leverage AI as your assistant.
Most organizations talk about "cloud" while hand-holding infrastructure. We're systematizing reliability across dozens of acquired products where the founding engineers have departed and the documentation is incomplete. That's the challenge: you'll apply agents and contemporary tools to examine unfamiliar systems 5–10x faster, document what you discover, and automate it so the same outage won't recur. Rather than evaluating you on certifications and vendor badges, we'll observe you troubleshoot in real time, produce a genuine 5-Whys that identifies one preventable root cause, and construct automations that endure production conditions.
This is not an L2 "execute the runbook" position. In this role, you author the runbooks, architect the deployment from dev to staged to 10% to 100% with soak periods and rollback triggers, and construct the monitors that detect the corner cases. You reject risky changes before anyone executes them. You distinguish infrastructure failures you own from application bugs Engineering owns, and you route permanent fixes to the appropriate team.
You'll operate at the engineering center of reliability, owning infrastructure initiatives, incident response and RCAs, and change requests with copy-paste-executable runbooks. If you've already owned a significant SaaS product and want to extend that discipline to an entire fleet, join us. Bring expert-level AWS, production-grade coding skills, ruthless scope discipline, and daily, critical use of AI tools. If you're prepared to keep the lights on, please apply.

What You Will Be Doing

• Complex infrastructure migrations, consolidations, production-grade automations, monitoring changes
• Triaging production outages, implementing immediate fixes, and writing root cause analyses with permanent fixes assigned to the responsible teams
• Creating, reviewing, and executing changes in production, including validating whether a proposed change is safe to execute

What You Won’t Be Doing

• Living in Jira and endless status meetings - we value people who can drive solutions, not just track problems
• Maintaining outdated systems indefinitely - you'll be empowered to drive meaningful improvements
• Getting blocked by bureaucratic approval chains - you'll have the authority to execute immediate fixes to resolve incidents

Senior DevOps Engineer Key Responsibilities

• Drive reliability and standardization of cloud infrastructure across our growing product portfolio by implementing 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-FR-COUNTRY-SeniorDevOpsEn

Key skills/competency

• DevOps Engineer
• AWS Expertise
• Production Support
• Infrastructure Automation
• Python Scripting
• Bash Scripting
• Database Management
• Incident Response
• Root Cause Analysis
• SaaS Product Management