Senior DevOps Engineer

Description:

You're the engineer who keeps 50+ SaaS products running when no one else knows where to start. We need DevOps engineers who can dive into unfamiliar AWS environments, bring order to disorder, and drive uptime beyond 99.9% through genuine monitoring, automation, and root cause analysis. You'll break down complex projects into daily tasks, deliver production-ready Python or JavaScript, and leverage AI as your assistant.

Most organizations talk about "the cloud" while manually maintaining infrastructure. We're building industrial-grade reliability across dozens of acquired products where original teams have departed and documentation is incomplete. The challenge: you'll use agents and contemporary tooling to explore new systems 5–10x faster, document your findings, and automate solutions so recurring incidents become impossible. Rather than evaluating your résumé for certifications and vendor badges, we'll observe how you troubleshoot in real time, author a genuine 5-Whys that identifies one preventable root cause, and create automations that withstand production conditions.

This is not an L2 "follow the runbook" position. Here, you author the runbooks, architect the deployment from dev to staged to 10% to full rollout with soak intervals and rollback criteria, and construct the monitors that detect edge cases. You block risky changes before execution. 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 foundation of reliability, taking ownership of infrastructure initiatives, incident response and RCAs, and change requests supported by copy-paste-ready runbooks. If you've already operated a substantial SaaS product and want to apply that rigor across a portfolio, join us. Bring advanced AWS knowledge, production-quality coding ability, disciplined scope management, and daily, mission-critical use of AI tooling. If you're prepared to maintain uptime, please apply.

What You Will Be Doing

• Leading complex infrastructure migrations, consolidations, production-quality automations, and monitoring enhancements
• Diagnosing production outages, deploying immediate remediation, and authoring root cause analyses with permanent fixes routed to the accountable teams
• Drafting, reviewing, and executing production changes, including assessing whether a proposed change is safe to proceed

What You Won’t Be Doing

• Spending time in Jira and continuous status calls - we reward people who deliver solutions, not simply document issues
• Preserving legacy systems forever - you'll be enabled to pursue substantial improvements
• Waiting on bureaucratic approval processes - you'll possess the authority to implement immediate fixes during 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

• Advanced AWS infrastructure knowledge (this is our core platform - experience with other clouds alone is insufficient)
• Background managing production infrastructure operating at a scale of hundreds of containers
• Background scripting with Python and Bash for routine administration tasks
• Background managing and migrating production databases across multiple engines (including MySql, Postgres, Oracle, MS-SQL)
• Background 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.