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

You're the engineer who maintains uptime across 50+ SaaS products when nobody else knows where to start.

We need DevOps professionals capable of entering unknown AWS environments, restoring order, and driving availability beyond 99.9% through genuine monitoring, automation, and 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 infrastructure" while manually tending servers.

We're systematizing reliability across a portfolio of acquired products whose original teams have departed and whose documentation is incomplete.

That's where the challenge lies: you'll harness agents and current tooling to explore unfamiliar systems 5–10x faster, document your findings, and automate solutions so recurring failures become impossible.

Rather than judge you on certifications and vendor badges, we'll observe how you troubleshoot in real time, author a genuine 5-Whys that identifies one actionable root cause, and construct automations that endure in production.

This is not a tier-two "follow the runbook" position.

Here, you author the runbooks, architect the deployment path from development through staging to 10% rollout to full release with soak periods and rollback conditions, and create the monitoring that captures corner cases.

You block risky changes before execution.

You distinguish between infrastructure failures under your ownership and application bugs owned by Engineering, then route permanent remediation to the correct team.

You'll operate at the engineering center of reliability, taking charge of infrastructure initiatives, incident response with RCAs, and change requests accompanied by copy-paste-ready runbooks.

If you've already operated a substantial SaaS platform and want to apply that expertise across an entire fleet, join us.

Bring deep AWS knowledge, production-quality coding ability, strict scope discipline, and daily, mission-critical use of AI tooling.

If you're prepared to ensure continuous operation, please apply.

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.