Lead Ruby Developer

Lead Software EngineerOur client is seeking a high-impact, senior-level engineering leader to take full ownership of our core software platform and engineering function. This role is designed for someone who can lead, architect, and execute - not just contribute. You will serve as the technical leader of the organization, responsible for driving platform evolution, leading a small team, and directly contributing to the codebase. This individual will play a critical role in modernizing infrastructure (Heroku to AWS), integrating AI into development workflows, and owning end-to-end system performance and delivery.This role is fully remote. Applicants must reside in the Chicago, Illinois area to meet with teammates on occasion.What You’ll DoTechnical Leadership & OwnershipOwn the end-to-end delivery of the core Ruby on Rails platform (architecture, performance, reliability, and scalability)Lead and mentor a small team of engineers while remaining hands-on in developmentDrive technical direction, system design, and engineering best practicesBalance coding, coordination, and strategic decision-makingPlatform & InfrastructureLead migration from Heroku to AWS, including infrastructure design and implementationOwn DevOps practices including CI/CD pipelines, deployments, environments, and monitoringTake responsibility for production systems, incident response, and system healthAI & InnovationChampion AI as a core part of the development processLead efforts around implementing, integrating, and debugging AI-driven codeHelp establish structured workflows that incorporate AI tools into engineering practicesCross-Functional CollaborationPartner with founders and business stakeholders to translate needs into technical solutionsImprove operational workflows across purchasing, fulfillment, warehouse operations, and reportingIdentify and execute on opportunities to increase efficiency, visibility, and automationHands-On DevelopmentContribute directly to the codebase, especially for complex features and system designTroubleshoot production issues and optimize performanceModernize legacy components while maintaining business continuityWhat We’re Looking For10+ years of software engineering experienceStrong background in Ruby on Rails (7+ years in production environments)Proven experience leading teams and owning delivery (not just contributing)Deep experience with AWS and DevOps practices (deployments, infrastructure, CI/CD)Experience with or exposure to platform/infrastructure migrationsStrong experience with Postgres or MySQLAbility to operate with full ownership in a complex, production environmentLeadership & Working StyleDemonstrated ability to lead small teams and mentor engineersComfortable balancing hands-on coding with coordination and leadershipAdaptable and effective in a fast-paced, evolving startup environmentOpen to and experienced with AI-assisted development workflowsNice to HaveExperience with logistics, warehouse, or inventory systemsBackground in React or modern frontend frameworksExperience modernizing legacy systemsExposure to hardware integrations (barcode scanners, automation, etc.)Experience working with large datasets