Top Tech Jobs & Startup Jobs in Chicago, IL

Design, operate, and scale end-to-end data infrastructure and pipelines. Build reusable data models and a semantic layer, ensure data quality and privacy, implement observability and SLAs, support marketing and growth feeds, partner with cross-functional stakeholders, and enable ML/AI consumption and reverse ETL workflows.

Own and deliver full-stack features across Ruby on Rails backend, React web, and Flutter mobile. Translate user needs into pragmatic solutions, drive architecture and production deployments, mentor teammates, address technical debt, and ensure reliability, performance, and security for mission-critical healthcare systems.

Lead and mentor a team of 3–4 Account/Client Success Managers to ensure client satisfaction, resolve escalations, monitor KPIs (retention, SLA, turnaround), maintain accurate reporting (Clockify/Sheets), drive onboarding and retention strategies, implement process improvements, and coordinate cross-functionally with HR, Operations, and Technical teams.

Lead enterprise application implementations and integrations for electric energy clients. Manage scope, schedule, budget, risks, Agile ceremonies, Azure DevOps artifacts, testing, data migration, vendor coordination, stakeholder alignment, and deployment/transition activities to deliver business value.

Freelance tester to perform smoke testing on an iOS wagering app during low-traffic updates (3:00–5:00 AM). Duties include creating a legal consumer account (KYC), running core wagering flows, capturing evidence (screenshots/screen recordings), and reporting functional issues, crashes, and UI defects. Paid hourly.

Lead global trade compliance as a Licensed Customs Broker, build scalable programs, improve classification and broker SOPs, launch KPI dashboards, drive duty optimization strategies, and present compliance roadmap and savings to leadership while partnering cross-functionally.

Serve as the senior client-facing technical lead to design and build data-generation, labeling, and evaluation pipelines for LLMs. Partner with executive stakeholders, diagnose data needs, architect multi-stage automated solutions (RAG, agentic workflows, synthetic data), run experiments, deliver production-ready pipelines, mentor engineers, and own delivery timelines and commercial outcomes.

Lead and coach a distributed outbound BDR team across North America and EMEA. Own outbound execution, SQO generation, quotas, hiring, onboarding, and ramp planning. Partner with Growth Marketing, Sales, and RevOps to optimize messaging, sequencing, and pipeline metrics. Diagnose funnel bottlenecks and improve conversion. Co-own and iteratively improve the inbound AI SDR engine, prompts, routing, and handoffs.

Lead and support security accreditation and RMF processes, develop and review authorization packages, conduct security control and risk assessments, manage POA&Ms and continuous monitoring, perform vulnerability assessments, support audits, and coordinate remediation with system owners and stakeholders.

Lead strategic account planning and execution for national on-premise chain customers to drive product availability, menu placements, and sales growth. Use data and analytics to build forecasts, monitor KPIs, and report performance. Collaborate with sales, brand, and distributor partners to launch programs, ensure in-market execution, and conduct senior-level business reviews. Travel ~40% and manage regional initiatives to exceed category and competitive benchmarks.