Top Tech Jobs & Startup Jobs in Chicago, IL

Own the strategy, requirements, metrics, and user experience for an AI-powered school scheduling optimizer. Partner with engineering on algorithms, model builders, orchestration, experiments, and generative AI capabilities. Engage school customers, define optimization quality measures, communicate tradeoffs, prioritize enhancements, and guide roadmap execution for improved schedule feasibility, quality, and usability.

Own portfolios of school and district accounts, guiding partners through onboarding, training, scheduling, data integration, troubleshooting, and renewal. Build strategic relationships with school leaders, support master schedule development, track success metrics, coordinate cross-functional improvements, and contribute to sales demos. The role requires substantial secondary-school scheduling experience, school operations knowledge, strategic communication, and the ability to manage complex priorities in a growing environment.

Design, build, and maintain optimization technology, full-stack systems, and data-intensive scheduling infrastructure. Improve optimization algorithms using linear optimization, machine learning, and generative AI. Lead complex technical initiatives, establish testing and observability, support scalable operations, troubleshoot customer issues, participate in on-call rotations, and mentor engineers while partnering closely with product and engineering teams.

Leads multiple product engineering squads, owning delivery, architecture, technical priorities, production quality, security, scalability, staffing, hiring, retention, performance management, and team health. Partners with Product and cross-functional stakeholders to align engineering work with business goals, resolve delivery blockers, improve processes and tooling, and manage major technical decisions. Requires hands-on experience with demanding architectures and the ability to work across React, Python, AWS, and MongoDB technology stacks.

Lead platform and infrastructure engineering to improve stability, developer productivity, CI/CD, observability, and shared libraries. Deliver platform projects, mentor engineers, own production availability and on-call, and drive platform decisions and best practices across the org.