Senior Ruby Rails Jobs in Chicago, IL (NOW HIRING)

About Invoca:

Invoca is the leading AI-powered conversation intelligence platform. We empower marketing, sales, customer experience, and contact center teams to unlock the intent and insights within every customer interaction – driving better customer experiences, increased revenue, and improved operational efficiency. Join our dynamic, fast-growing team, where innovation and collaboration are at the core of our culture.

About the Team:

Octothorpe is a platform multiplier team: we build, maintain, and support tooling for connecting pieces of the platform (gems/libraries, CI/CD, shared infrastructure patterns) to improve the lives of service owners.

Invoca's Release Engineering "North Star" is that any change that supports a service (code/config/infra/secrets/process settings) flows through a standard build & deploy process with CI, config validation, security checks, health checks, and rollback quickly and reliably.

Octothorpe owns and evolves the tooling and processes that power developer autonomy, automation, standardization, tight feedback loops, and staging/production parity.

About the Role:

As a Senior Software Engineer I on Octothorpe, you'll be an individual contributor reporting to the Sr. Software Engineering Manager. You'll focus on turning our internal engineering platform vision into reality by strengthening our CI/CD, driving key Ruby/Rails platform upgrades, and making authentication/authorization safer and more standardized across services.

You'll operate as an expert within the team's domains: solving large-scope problems, leading small efforts from design through rollout, and helping your teammates remove bottlenecks. The work is highly cross-functional and platform-oriented.

You Will:

• Build and maintain reliable, scalable CI/CD workflows (guardrails, automation, reusable patterns/templates).
• Enhance Backstage as the unified developer portal, improving CI/CD visibility, deployment tracking, and self-service workflows.
• Improve developer feedback loops: reduce flaky pipelines, speed up builds/tests, and increase observability of the release toolchain.
• Operationally support release tooling (triage, incident follow-ups, preventative improvements).

• Lead or heavily contribute to Ruby and Rails upgrade efforts, including:
• Coordinating cross-repo changes (application, Docker/CI images, shared gems, test strategy).
• Creating safe rollout plans (canaries, staged deploys, rollback paths) and enabling other teams through docs/runbooks.

• Build and improve self-service tooling and Golden Path workflows through Backstage, CI/CD templates, and standardized patterns so service teams can safely own their own infra, config, and auth changes without gatekeepers.
• Help standardize and operationalize Auth0 and other authentication/authorization patterns across environments
• Partner with service teams to drive Golden Path adoption, unblock migrations, and turn platform investments into org-wide leverage.

• Use AI-assisted development responsibly to increase throughput and quality (e.g., faster iteration, better testing strategies, improved docs/runbooks).
• Help the org adopt AI tools safely and effectively by sharing best practices and patterns.

You Have:

• CI/CD, Release Engineering, (Buildkite/Backstage)
• ArgoCD, Kubernetes
• Ruby, Ruby on Rails, Bundler, dependency management
• Runtime/framework upgrades (Ruby upgrades, Rails upgrades)
• Auth0 (or similar IdP), OAuth/OIDC concepts, M2M authentication
• Terraform / infrastructure-as-code (nice-to-have)
• Observability, on-call/operational support, incident analysis
• AI-assisted development (Cursor, Claude Code) and best-practice sharing
• Working experience in a PAAS environment

📍 Location This is a remote-first role. We are currently hiring in the following locations: 📍

United States: Greater Los Angeles Area (including Santa Barbara and San Diego) · SF Bay Area · Denver Metro · Austin Metro · Chicago Metro · Greater NYC Area

Canada: Toronto (AI/ML technical roles only)

Candidates must be based within ~2 hour drive of these areas. Occasional business travel may be required.

At Invoca, all new hires in the U.S. receive benefits starting on day one of employment. Our benefits offerings include:

Please note that benefits for teammates outside the U.S. may vary in accordance with their country's laws and regulations.

• Flexible Time Off – We encourage a healthy work-life balance. Our flexible paid time off policy allows you to recharge and take time away as needed.
• Paid Holidays – Invoca provides 16 U.S. paid holidays, including a winter break, giving you ample opportunity to refresh and spend time with friends and family.
• Health Benefits – Our healthcare program includes medical, dental, and vision coverage, with multiple plan options so you can choose what works best for you and your family. Fertility assistance is also included.
• Retirement – Invoca offers a 401(k) plan through Fidelity with a company match of up to 4%.
• Stock Options – All employees are invited to share in Invoca's success through stock options.
• Mental Health Program– Well-being support on a broad range of issues is available through our SpringHealth program.
• Paid Family Leave – Up to 12 weeks of 100% paid leave is provided for baby bonding, adoption, and caring for family members.
• Paid Medical Leave – Up to 12 weeks of 100% paid leave is provided for childbirth and medical needs.
• InVacation – As a thank-you to our long-term team members, we offer a bonus after 7 years of service.
• Wellness Subsidy – We provide a subsidy that can be applied toward gym memberships, fitness classes, and more.
• Position Base Range - Salary Range $127,000-$191,000 / plus bonus potential

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.

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