Independent Contractor Ruby Rails Developer Jobs in Chicago, IL

• Forbes: For Pair Team, Accessibility Is About Delivering Healthcare To Those Who Need It The Most
• TechCrunch: Building for Medicaid's regulatory moment with Neil Batlivala from Pair Team
• Journal of General Internal Medicine: A Novel Intervention for Medicaid Beneficiaries with Complex Needs
• Pair Team Accepted into CMS ACCESS Model to Expand AI-Enabled Care for Medicare Beneficiaries

We're hiring a Senior Platform Engineer to build the infrastructure and shared engineering capabilities that will enable Pair Team to scale. This role will own foundational systems and patterns that make it easier for product and engineering teams to build, deploy, integrate, and operate services safely and independently.

You'll work at the intersection of cloud infrastructure and application engineering to create the core services and capabilities that teams across Pair Team depend on. This is a highly leveraged role: rather than building for one product team, you'll build the platform that enables every product team to move faster.

The ideal candidate brings a deep expertise in AWS and Terraform while also being comfortable working in our Ruby on Rails codebase. 

This is a fully remote position reporting up to the Engineering Manager.

• Own the shared platform layer across the systems we operate, including our Patient Care Application, AWS, Vendor Integrations, , Postgres, Snowflake, Github, CI/CD, and other critical systems.
• Establish reusable patterns and conventions so engineers can interact with unfamiliar infrastructure consistently and confidently.
• Design and improve cloud infrastructure with a focus on scalability, reliability, security, and developer experience.
• Build core application services in Ruby on Rails, including foundational capabilities around authorization/RBAC, jobs and queues, deployments, and integrations.
• Own foundational infrastructure and services that sit beneath our product teams, including platform, IAM, HIE, EMR, and integration layers.
• Improve developer experience and engineering velocity by identifying infrastructure bottlenecks and turning manual processes into reliable, self-service workflows.
• Build for scale, ensuring our platform can support significant growth in engineering teams, products, integrations, and infrastructure without creating operational bottlenecks.
• Partner closely with product and engineering teams to understand their needs and build platform capabilities that make their work easier and faster.
• Set technical standards and architectural conventions that other engineers and teams can build upon.
• Operate production infrastructure, participating in troubleshooting and improving the reliability and resilience of critical systems.

What You'll Need 

• 5+ years of software engineering experience as a high-performing individual contributor, building and operating production backend systems
• Deep expertise in Ruby on Rails with strong understanding of both application and data layers and hands-on experience building and maintaining core backend services
• Strong relational database skills, including data modeling and query optimization: reading query plans, resolving slow queries and N+1s, and getting indexing right
• Experience building and operating platform-level capabilities such as authentication/RBAC, jobs and queues, CI/CD, deployments, integrations, and other shared services that enable engineering teams to move independently.
• Ability to work across the application and infrastructure layers—you're an application engineer who is comfortable getting into infrastructure, or a cloud/platform engineer who is willing to work deeply in Rails. 
  • AWS and Terraform experience are a plus, but not required.
• Proven experience tackling the hard parts of production engineering, such as major Rails upgrades, significant database migrations, zero-downtime schema changes, large-scale data backfills, dependency upgrades, and security remediation.
• A track record of keeping a production codebase current on its dependency and package upgrades, treating that maintenance as steady, ongoing work
• Strong systems thinking and technical judgment, with the ability to establish reusable patterns, conventions, and abstractions that make complex systems easier for other engineers to understand and operate.
• Builder mindset with a bias toward execution, ownership, and pragmatic problem-solving
• Strong collaboration skills, comfortable partnering across engineering, product, and operations

• Lead with integrity: We keep our commitments and take responsibility for our actions. We are dependable and choose authenticity over perfection.
• Embrace challenges: We leave our egos at the door and step forward into discomfort instead of back into safety. We help each other to learn and provide feedback using candor and kindness.
• Break through walls: We go the extra mile for our patients, partners and one another, and we run toward hard things. We are resilient in our push for consistent improvement and challenge the status quo.
• Act beyond yourself: We build each other up and respect boundaries. We seek first to understand and assume positive intent.
• Care comes first: We hold ourselves to the highest standards for our patients. We are relentless in the pursuit of our mission, and ensure that we are taking care of ourselves in order to care for others.

• Competitive salary: $180,000 - $220,000
• Equity compensation package
• Medical, dental & vision with HSA/FSA and company HSA contribution
• Remote-first with equipment and $100/mo home office stipend
• Flexible PTO and 12 paid holidays
• 100% company-paid life, disability & AD&D
• Backup childcare, caregiver concierge, and financial guidance resources