Senior devops engineer Jobs in Chicago, IL

The role

You will keep that platform reachable, fast, secure and deployable. Our sites run on WP Engine behind Cloudflare, with menus and checkout powered by Sweed, our e-commerce and POS platform, and we release to production every week. You will own production access, the edge, CI/CD and the release process, and build the automation that lets the rest of the team ship safely without waiting on you.

This is a hands-on seat on a Scrum team. You write code, review code and take sprint commitments like everyone else.

While this position is listed in Chicago, IL, candidates may work remotely, provided they reside in a state where Verano currently has business operations. Remote eligibility is limited to these states and is subject to company approval.

What you will own

• Access and credentials. Production credentials and access across our hosting, edge and third-party services, including rotation and least-privilege design.
• The edge, as code. Cloudflare across our brand sites: DNS, TLS, caching, security rules and Workers, with configuration managed in Git and deployed through CI.
• Releases. The weekly release, hotfixes and rollbacks. Every release is traceable and verified after it ships.
• CI/CD. GitHub Actions pipelines, required checks and branch protection. Repeated manual checks become automated gates.
• Monitoring and incidents. Error tracking, uptime and performance monitoring, including our Sweed integration, that alerts when something breaks. You are available around the clock to respond to true emergencies, such as a site outage, and you write blameless incident reviews afterward.
• Performance. Root-cause fixes for origin and edge errors, and Next.js caching strategy together with the frontend engineers.
• Dependency security. Triage advisories by real risk and ship upgrades through review and testing.
• Automation. Tested internal tooling in Python or TypeScript for GitHub, Jira and our delivery process.
• New brand sites. Stand up the infrastructure for each new site (repository, hosting, edge, monitoring and access), and turn the launch runbook into automation.
• Contractors. Direct and review the work of UpWork contractors assigned to platform work.

Your first 90 days

• Days 1 to 30: Learn the platform from our runbooks, shadow a release, then take over release preparation, credential management, and Cloudflare and CI/CD work.
• Days 31 to 60: Run the next scheduled credential rotation, move edge deployments into CI, and clear critical dependency alerts.
• Days 61 to 90: Improve origin and edge performance against agreed targets, make every deploy verifiable by build, and get delivery metrics measured.

How we work

We run two-week sprints and ship weekly. Every change has a ticket and a reviewer, including a DNS record or a cache rule. Pull requests stay small and get reviewed the same day. Blockers are raised the day you hit them, and every retro item becomes a ticket with an owner.

AI coding tools such as Claude Code and Cursor are part of how we work every day. We want someone who already works this way, gives those tools good context, and checks their output against the spec rather than trusting a green build. An agent's verdict is never an approval, and credentials never go into prompts.

What you bring

• 5+ years of DevOps, platform or SRE work on production web applications.
• Cloudflare at production depth, including Workers you have written and deployed.
• GitHub Actions and release strategy for a team that ships weekly: tagging, hotfixes, rollback.
• Secrets management, credential rotation and least-privilege access.
• Observability with Sentry and an APM such as New Relic or Datadog.
• Tested automation in Python or TypeScript.
• Scrum team experience, daily use of AI coding tools, and clear writing: runbooks and incident notes a teammate can follow at 2 a.m.

Nice to have

• WP Engine or another managed WordPress host.
• Next.js in production from the infrastructure side.
• Terraform or another infrastructure-as-code tool.
• Load testing and DORA metrics.
• Jira administration and automation.
• Regulated industry or multi-brand e-commerce experience.

What We Offer

Verano Base Pay Range

$85,000 - $100,000 + Bonus

Actual pay is based on experience, qualifications, and location of the role. Roles may be eligible for annual bonus program based on individual and company performance.

Benefits:

• Medical, dental, and vision insurance
• 401(k) matching
• Paid holidays
• Paid time off
• Product discounts

Physical and Mental Demands

While performing the duties of this job, the employee is frequently required to remain in a stationary position, move and/or position oneself, communicate, operate and/or prepare, place, position objects, tools, or controls. The employee must occasionally move packages weighing up to 10 lb. Specific vision abilities required by this job include close observation and the ability to adjust focus. The mental and physical requirements described here are representative of those that must be met by an individual, with or without reasonable accommodation, to successfully perform the essential functions of this position.

Working Environment

Work is performed in an office environment. The noise level in the work environment is usually moderate. The work environment characteristics described here are representative of those an individual encounters while performing the essential functions of this position.