Remote Helicopter Flight Engineer Jobs in Chicago, IL

In the journey of your life, your career should make a difference.

At Inizio Evoke, we come together-to do the best work, in the best possible place. We're all in. Because it's everyone's role to make health more human.

About the Role

We're looking for a DevOps engineer who takes genuine pride in keeping production systems healthy, secure, and humming. You'll own the infrastructure behind a cutting-edge agentic AI platform - from day-to-day operations to architectural decisions - and operate as a trusted peer on a collaborative platform team. This is a hands-on individual contributor role; the Director title reflects the scope of ownership and independence we expect, not the size of a team you'll manage.

This is a fully remote opportunity.

What You'll Do

Operations & Reliability

• Support, monitor, and operate a production agentic AI platform running on AWS
• Ensure all services are up, responsive, and scaling appropriately under real-world load
• Own incident response end-to-end - triage, resolve, document, and follow through on prevention
• Manage infrastructure across multiple AWS accounts spanning production and non-production environments
• Lead release management and weekly operational rituals to ensure enhancements reach production smoothly

Infrastructure & Automation

• Infrastructure as code is the way - we're a team that builds, deploys, and evolves everything through automation.
• Research and evaluate new solutions to cloud infrastructure challenges; bring recommendations, not just options
• Enforce engineering best practices with conviction - you understand why doing it right matters, even when shortcuts are tempting
• Take rough direction, identify and propose solutions, gather feedback, and ship

Security & Compliance

• Monitor security tooling and participate in security scans and vulnerability reviews
• Ensure the platform stays compliant with security and data protection requirements
• Treat compliance as an engineering concern, not a checkbox exercise

Collaboration & Process

• Manage a backlog, track work in flight, and report progress clearly and regularly to stakeholders
• Collaborate with the platform development team on changes and deployments - you're a peer at the table, not a downstream recipient
• Participate actively in agile ceremonies: daily standups, sprint planning, and sprint reviews/closures
• Partner with the platform development on sprint priorities, product backlog, and cross-team dependencies.
• Surface issues early and proactively; the team shouldn't have to ask how things are going

What You'll Bring

Experience

• 8+ years of hands-on DevOps or platform engineering experience at senior or staff/director level
• Demonstrated ownership of production SaaS environments - you've been the person on the hook when things break
• A track record of making sound, independent infrastructure decisions without creating downstream chaos

Technical

• Deep AWS expertise, including multi-account management and production SaaS environments
• Infrastructure as Code fluency in Terraform, AWS CDK, or both
• Solid software engineering fundamentals - writes production-quality code in Python and TypeScript
• Automation-first instincts - uses software to eliminate manual work and prevent future toil
• Serverless infrastructure experience
• Centralized logging and log management at scale
• Metrics, monitoring, alerting, and reporting tooling
• Experience with structured release management processes

Ways of Working

• Highly organized - you run a backlog, track commitments, and communicate status without being asked
• Proactive by default - you surface problems early and come with a proposed path forward
• Comfortable in ambiguity - you can take rough direction and figure out the rest
• Intellectually honest - you share your opinion clearly, then fully support the group's decision
• Deeply aware of the cost of complexity - you know that complexity can be moved, but it's rarely erased; every decision to add it is a decision you're willing to own long-term
• You treat engineering as a craft; this work should feel meaningful, not mechanical

Work Environment & Benefits

Inizio Evoke offers a fully remote work environment, competitive compensation, and outstanding company-paid benefits, including medical, dental, 401(k), tuition reimbursement, and flexible time off.

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender, gender identity or expression, or veteran status. We are proud to be an equal opportunity workplace.