Senior DevOps Engineer, Trilogy (Remote) - $100,000/year USD
Crossover
fulltime
Engineering and Information Technology
5+ years
You're the engineer who stabilizes production when no one else knows where to start. We need DevOps engineers capable of stepping into unknown AWS environments, restoring order from disorder, and driving uptime beyond 99.9% through rigorous monitoring, automation, and root-cause analysis. You'll break down complex projects into executable one-day increments, deliver production-ready Python or JavaScript, and leverage AI as an accelerant.
Most organizations talk about "cloud transformation" while hand-holding fragile systems. We're building industrial-grade reliability across dozens of acquired SaaS offerings where original engineers have departed and documentation is incomplete. The challenge: you'll deploy agents and cutting-edge tooling to map unfamiliar systems 5–10x faster, document your findings in code, and automate remediations so repeat incidents become impossible. Rather than judging you on certifications and vendor badges, we'll observe how you diagnose live issues, produce a meaningful 5-Whys analysis that identifies a single preventable root cause, and construct automations resilient enough for production deployment.
This is not a tier-two "execute the runbook" position. Here, you author the runbooks, architect the deployment pipeline from development through staging to canary and full rollout with soak periods and rollback triggers, and instrument the monitoring that surfaces obscure failure modes. You reject hazardous changes before they reach production. You distinguish infrastructure failures under your ownership from application bugs that belong to Engineering, and you route permanent remediations to the correct team.
You'll operate at the engineering heart of reliability, driving infrastructure initiatives, incident management and RCAs, and change execution with copy-paste-ready runbooks. If you've already run a significant SaaS platform and are ready to apply that expertise across an entire portfolio, this is your opportunity. Bring deep AWS knowledge, production-caliber coding ability, disciplined scope management, and daily, mission-critical use of AI tooling. If you're prepared to keep systems running, apply now.
What You Will Be Doing
What You Won’t Be Doing
Senior DevOps Engineer Key Responsibilities
Basic Requirements
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-GB-COUNTRY-SeniorDevOpsEn.004