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

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

Base pay range: $50.00/hr – $50.00/hr

You\’re a DevOps engineer who prioritizes prevention over remediation. If you find satisfaction in dissecting convoluted legacy systems, architecting more robust replacements, and automating every repetitive workflow you discover, this opportunity is worth your attention.

We need a DevOps and AWS infrastructure specialist who excels under pressure, where 99.9% uptime is the baseline expectation. Your work will span a portfolio of acquired products, each presenting unique challenges, as you migrate them into a unified, scalable AWS environment while implementing monitoring and automation that genuinely minimizes incident frequency.

Most organizations ask you to support a single technology stack. We\’re asking you to unify and enhance multiple stacks without introducing disruption. Where other companies isolate databases, our approach involves strategic consolidation to maximize cost efficiency and simplify management across the portfolio. This position isn\’t designed for someone content with maintaining existing infrastructure; it\’s intended for someone who encounters fragmented, inconsistent environments and immediately envisions a superior architecture.

Your ownership will extend from infrastructure migrations through AI‑powered automation, performance optimization, database transitions, and cost management. This means identifying and resolving current issues, orchestrating smooth cloud migrations with minimal downtime, and building AI/ML‑driven workflows that automate significant portions of operational work. You\’ll possess genuine authority to make infrastructure decisions—no delays waiting for sign‑off from stakeholders disconnected from the technical reality.

If you’re a self‑directed problem‑solver who enjoys systematizing complex environments and ensuring flawless operation, this role offers substantial opportunity. If you require close supervision, struggle with managing diverse technology stacks, or favor greenfield projects over bringing structure to chaos, this position will not be a good fit. If you’re prepared to assume ownership of a high‑impact infrastructure function with latitude to build, optimize, and automate at scale, submit your application now!

What You Will Be Doing

• Orchestrating and implementing sophisticated infrastructure transformations, including transitions from legacy platforms to AWS cloud environments and lift‑and‑shift migration projects
• Architecting and deploying monitoring strategies while creating automation for monitoring systems, software deployment pipelines, and operational processes
• Executing system monitoring, backup procedures, incident management, database migration projects, database configuration, and cost reduction initiatives

What You Won’t Be Doing

• Spending your time in Jira and protracted status meetings – we prioritize people who deliver solutions, not merely document problems
• Supporting legacy systems in perpetuity – you\’ll be authorized to implement substantive improvements
• Waiting on bureaucratic approval processes – you\’ll possess the authority to deploy immediate remediation during incidents
• Operating within restrictive technical specializations – this position demands both comprehensive knowledge and specialized expertise
• Justifying budget requests for essential infrastructure work – we recognize the value of infrastructure investment

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)
• Strong programming skills in Python or JavaScript for building automation and tooling
• Experience managing and migrating production databases with multiple engines (including MySQL, Postgres, Oracle, MS‑SQL)
• Advanced Docker/Kubernetes skills
• 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 three 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.

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.