Ruby on Rails Engineer, Automation Systems
Job Type: Permanent
Salary: $100k–$160k + Equity (DOE)
Role Location: Chicago (Onsite Only)

The Company

We've partnered with a fast-growing early-stage fintech startup building a platform that helps financial institutions activate new accounts and establish primary customer relationships faster.

Their technology automates complex workflows across hundreds of third-party websites — securely navigating web environments, submitting forms, and coordinating financial data across external systems.

The core automation engine is already live and functioning. The next phase is scaling the platform by expanding integrations and strengthening the backend infrastructure that powers these workflows.

They operate with a small, senior engineering team and are looking for a Rails engineer who enjoys building backend systems that support complex real-world automation.

The Role

They're hiring a Ruby on Rails Engineer, Automation Systems to help build and scale the backend services that power their automation platform.

The system already works at an MVP level, and the focus now is on turning it into a reliable, production-grade platform while dramatically expanding the number of supported integrations.

This role centers on building and maintaining the Rails services, internal tooling, and data structures that support the automation engine.

It's a hybrid backend engineering + systems ownership role. You'll help build the platform while also working closely with the automation workflows themselves, improving reliability and scalability as the system grows.

This is an early and high-impact role where you’ll work directly with senior engineers and help define the foundation for a larger automations and integrations team as the company scales.

What You'll Do

• Build and maintain backend services using Ruby on Rails
• Develop internal tools and systems that generate and maintain structured automation data
• Expand integration coverage across a large and growing set of third-party websites
• Improve reliability by building break detection and recovery strategies for automations running in production
• Collaborate with engineers working on browser automation and frontend tooling
• Design scalable processes and documentation as integrations grow from dozens to thousands
• Contribute to improvements in the core automation engine
• Help shape technical decisions as part of a small, highly collaborative engineering team

Ideal Background

• 3+ years of professional Ruby on Rails development experience
• Strong backend engineering fundamentals and experience building production web applications
• Experience designing APIs and backend services
• Comfort working with JavaScript or TypeScript in web environments
• Experience building internal tools or automation-heavy systems
• Strong debugging skills and ability to work through edge cases across distributed systems
• Comfortable designing processes and documenting technical workflows
• Self-starter mindset — able to operate effectively in ambiguous problem spaces

Nice to Have

• Experience with web automation tools such as Puppeteer, Playwright, Selenium, or similar
• Experience building or maintaining browser extensions
• Experience with Python or Node.js
• Experience working with LLM-assisted pipelines, prompt engineering, or structured output validation
• Background in data engineering, web scraping, or automation-heavy roles

Benefits

• Competitive base salary + equity
• Remote-friendly team
• Health, dental, and vision benefits
• High ownership role within a small engineering team
• Opportunity to help build and scale a complex automation platform from the ground up