Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as COO/CAO Chief of Staff to coordinate and drive enterprise strategic initiatives, lead special projects, support board relations, provide decision support and stakeholder alignment, monitor high-priority programs, mentor staff, and represent the COO/CAO as needed. Provide analysis, prioritize requests, support meetings and communications, and manage resources to ensure organizational objectives are met.

Evaluate AI-generated responses for business users by comparing outputs against professional email history, assessing relevance, accuracy, personalization, and providing detailed feedback to improve models while maintaining data privacy.

Evaluate AI-generated responses for business users by reviewing personalization against your professional Gmail history. Rate relevance, accuracy, helpfulness, and personalization; compare responses; identify incorrect personalization or unsupported assumptions; provide clear, structured feedback while following guidelines and maintaining data privacy.

Evaluate AI-generated responses using your personal Gmail account to assess relevance, personalization, accuracy, and helpfulness across English and German. Provide detailed feedback, compare responses, identify incorrect personalization or unsupported assumptions, and follow confidentiality and consent procedures.

C-suite growth leader responsible for go-to-market strategy and execution to drive revenue across acquisition, retention, and expansion. Oversees marketing, sales, and customer service; manages brand portfolio, revenue systems and tech stack, campaign and channel performance, and talent. Partners with product to define offers and measures success via volumes, velocity, and lifetime value metrics.

Design, build, and maintain ETL pipelines and data warehousing for RCM-focused analytics. Perform gap analysis for new business onboarding, optimize ETL performance, monitor production jobs, partner with development on database and analytics projects, and author technical documentation while supporting deployments and change control.

Enable Microsoft partners across Asia to use investment programs, coach on pipeline and co-sell readiness, manage operational requests and KPIs, generate partner insights, and liaise with internal stakeholders to improve partner performance.

Hire Principal Software Engineer as an independent contractor to support the Knowland team: manage transition tasks, support deliverables, maintain roadmap, and perform knowledge transfer while accommodating overlap time with the team.

Serve as the primary US IT contact, providing first-line support, managing helpdesk tickets, configuring and imaging devices via Workspace ONE, handling onboarding/offboarding and device lifecycle, maintaining IT asset records, and coordinating office infrastructure with vendors to ensure secure, reliable workplace technology.

Own and evolve ShiftKey's AI infrastructure: production retrieval/indexing, agentic platforms on AWS, graph-based multi-hop retrieval design, platform APIs, reference agents, and cost/observability guardrails for regulated (HIPAA) workflows.

Plan and execute risk-based internal audits, test controls, identify root causes of weaknesses, recommend remedial actions, and improve business processes and operational efficiency while adhering to GIA methodology.

Own and execute the group-wide payments strategy across a family of Bitcoin-native businesses. Define and operate ElenPay (PSP), expand PSP growth, integrate payments with the banking house, productize Bitcoin-native infrastructure (liquidity, routing, swaps, LSP services), and capture frontier rails (stablecoins, cross-border, machine-to-machine). Deliver roadmaps, commercialization, merchant funnels into banking services, and live liquidity/swap products in-market.