Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end provider onboarding projects involving Epic scheduling integrations, from contracting and configuration through testing, go-live, and operational transition. Manage project scope, plans, risks, timelines, reporting, stakeholder communications, executive presentations, and cross-functional coordination with engineering, product, sales, and customer teams. Drive continuous process improvement and deliver a high-quality provider customer experience across concurrent enterprise engagements.

Lead a complex federal infrastructure automation and modernization program supporting VA OIT. Manage multidisciplinary technical teams, subcontractors, schedules, risks, deliverables, staffing, contractual performance, security and RMF/ATO activities, governance, reporting, platform adoption, training, knowledge transfer, and transition. Coordinate infrastructure, cloud, automation, DevSecOps, IaC, cybersecurity, and IT service management workstreams across hybrid environments while ensuring cost, schedule, technical, and mission objectives are achieved.

Leads Federal Civilian business development, account growth, opportunity identification, capture, customer engagement, teaming, pipeline management, and contract wins. Builds relationships across agencies, translates mission requirements into growth strategies, develops competitive pursuit and pricing strategies, and coordinates with technical, contracts, pricing, recruiting, operations, and proposal teams. Maintains executive-level reporting and drives diversified revenue growth across multiple Federal Civilian accounts.

Own and evolve Argo Workflows and Argo Events, make major architectural decisions, and build Pipekit’s enterprise control-plane product. The role includes shaping the roadmap, shipping customer-focused features, engaging with open-source contributors and customers, participating in an on-call rotation, and speaking at cloud-native conferences. Candidates should have strong statically typed programming skills, Kubernetes expertise, production-systems experience, excellent written communication, and a self-directed, customer-focused approach.

Lead a team of 3–5 QA Engineers and own quality strategy, test planning, automation, regression coverage, defect management, and release readiness. Partner with Product and Engineering in Agile/Scrum processes, provide go/no-go recommendations, improve testing and documentation, and ensure audit-ready traceability for compliance software. The role is hands-on, emphasizing Playwright and TypeScript/JavaScript automation, risk-based testing, and clear communication of quality risks.

Manage and grow a regional team of Solutions Engineers supporting major accounts. Recruit, coach, and develop presales talent while serving as a player-coach and executive sponsor for key customers. Partner with sales, marketing, customer experience, product management, and engineering to drive pipeline, adoption, technical validation, and customer success. Own regional planning, team performance, account programs, and quarterly financial targets while influencing product strategy through customer feedback.

Leads regional project accounting, billing, revenue recognition, accounts receivable, cash flow forecasting, financial reporting, and project closeout activities. Oversees project setup in Oracle, reconciliations, compliance, audits, process improvements, and ERP enhancements. Manages project accounting staff, assigns workloads, develops KPIs, analyzes profitability, resolves billing disputes, and partners with project managers, operations, clients, and senior finance leadership.

Own PayBox end to end as a founding-style staff engineer, taking the AI payments product from problem definition through production and iteration. Build payment, peer-to-peer transfer, AI platform, application, and ecosystem integrations. Improve onboarding and UX, make pragmatic architectural decisions, collaborate with Product, and use AI tools while maintaining strong independent technical judgment.

Full‑stack product engineer role with backend emphasis: build scalable Node.js services, develop React + TypeScript UIs (React Router v7), design APIs (tRPC/OpenAPI), optimize PostgreSQL queries and data pipelines, improve observability and infrastructure, write well‑tested code, and contribute to architecture and engineering practices in a fintech product.

Lead the end-to-end product experience across acquisition, onboarding, avatar selection, chat, media generation, and retention. Drive conversion, retention, and LTV through hypotheses, prioritization, A/B testing, and data-informed design. Establish the product’s design direction and design system, lead a multidisciplinary design team, and partner with product, analytics, marketing, engineering, research, and support.