You are the engineer who ensures 50+ SaaS products remain operational when others are uncertain. We seek DevOps engineers capable of working through unfamiliar AWS environments, restoring stability from disorder, and driving uptime beyond 99.9% through genuine monitoring, automation, and root cause analysis. You will break down complex projects into single-day tasks, deliver production-quality Python or JavaScript, and leverage AI as an assistant.

Many organizations claim "cloud" expertise while manually managing infrastructure. We are systematizing reliability across numerous acquired products whose original developers have departed and whose documentation is incomplete. The challenge: you will employ agents and contemporary tools to explore unfamiliar systems 5–10× faster, document your findings, and automate solutions to prevent recurrence. Rather than evaluating credentials and tool familiarity, we will observe your live troubleshooting, review a genuine 5-Whys analysis that identifies a single preventable root cause, and examine automations that withstand production conditions.

This is not an L2 "execute the playbook" position. In this capacity, you author the playbooks, architect the deployment path from dev through staged to 10% to full rollout with soak periods and rollback conditions, and create monitors that detect edge cases. You reject hazardous changes before execution. You distinguish infrastructure failures you control from application bugs Engineering controls, and you route permanent corrections to the appropriate team.

You will operate at the engineering foundation of reliability, managing infrastructure initiatives, incident response with RCAs, and change requests accompanied by copy-paste-executable documentation. If you have already owned a substantial SaaS product and wish to extend that expertise across a fleet, join us. Bring expert-level AWS knowledge, production-grade development skills, rigorous scope discipline, and daily, critical application of AI tools. If you are prepared to maintain operational continuity, 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 authoring root cause analyses with permanent fixes routed to the responsible teams
• Authoring, reviewing, and applying changes in production environments, including assessing whether a proposed change is safe for execution

What You Won’t Be Doing

• Spending time in Jira and prolonged status meetings - we prioritize people who can deliver solutions, not simply monitor problems
• Supporting legacy systems indefinitely - you will be authorized to pursue substantive improvements
• Waiting on bureaucratic approval processes - you will 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 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 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 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-CA-Nunavut-DevOpsEngineer.012