Top Tech Jobs & Startup Jobs in Chicago, IL

Own the post-sale customer lifecycle for a portfolio of B2B SaaS customers, including onboarding, adoption, retention, expansion, and churn mitigation. Build trusted relationships with Operations and Finance stakeholders, provide purchasing and payments guidance, drive revenue and net retention, monitor support risks, and translate customer feedback into product improvements. Collaborate cross-functionally to identify strategic opportunities and strengthen customer advocacy.

Leads Engineering Operations by building the operating system connecting Product, Engineering, and Data strategy to measurable outcomes. Owns executive reporting, KPI and OKR definition, portfolio planning, software delivery reviews, capacity and headcount planning, risk and dependency tracking, and cross-functional decision-making. Partners with senior leaders across technology and business functions to improve delivery predictability, accountability, resource allocation, and organizational effectiveness.

Scale and evolve Order.co’s design system across legacy product experiences. Audit components, identify inconsistencies, create accessible production-ready patterns with engineers, establish system principles, and improve adoption and usability. The role also explores AI-enabled workflows for component discovery, documentation, quality checks, and pattern generation while balancing flexibility, consistency, and scalability.

Own the end-to-end architecture, development, deployment, evaluation, and operations of AI and machine learning systems. Build predictive ordering models, agentic workflow copilots, retrieval and evaluation infrastructure, safety guardrails, and responsible AI practices. Prioritize AI initiatives based on business outcomes, establish model governance and production standards, advise product and engineering leadership, and mentor experienced contributors.

The role involves ensuring software reliability and performance, managing incidents, developing infrastructure automation, and mentoring junior engineers within a platform team.

The Staff Security Engineer will lead technical security initiatives, own architectural security decisions, mentor engineers, and align teams on security strategy while ensuring system integrity and compliance.

The Senior Software Engineer will lead the development of payment systems, oversee key subsystems, mentor engineers, and ensure high-quality code and architectural standards while collaborating with cross-functional teams.