Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with sales to evaluate customer environments, architect infrastructure and security solutions, lead technical discovery and presentations, produce proposals, drive adoption and upsell, and maintain technical documentation and CRM records while ensuring information security and occasional travel.

Lead architecture and technical strategy for a remote engineering organization building a React, Node.js, PostgreSQL, and AWS platform. Mentor engineers, establish engineering standards, drive JavaScript-to-TypeScript migration, design ETL and AI/LLM integration systems, resolve technical debt, and oversee technical design reviews, production support, incident response, hiring, and delivery. Partner with product, clinical, and business stakeholders to build scalable, reliable software.

Manage the full lifecycle of federal proposals, including RFPs, RFQs, RFIs, task orders, Sources Sought notices, and sole-source submissions. Coordinate business development, technical, pricing, executive, and teaming contributors; develop compliance matrices, schedules, content plans, and submission materials; lead reviews; ensure compliance and timely delivery; identify risks; research federal opportunities; and maintain proposal resources and lessons learned.

Provide remote administrative support including calendar and email management, preparing reports and presentations, conducting research, compiling data, and performing general administrative tasks to ensure efficient office operations.

Support social media presence by creating, editing, scheduling posts; engaging followers; tracking analytics; helping run campaigns; maintaining content calendars and healthcare-relevant, compliant content.

Develop and execute a national sales strategy for Taft Hartley and multiemployer pension, health and welfare, and claims solutions. Build pipeline, manage complex enterprise sales cycles, cultivate relationships with trustees and fund executives, lead proposals and negotiations, and coordinate cross-functional pursuit teams. Translate customer needs into measurable value while maintaining forecasts, account plans, and sales targets in a specialized B2B market.

Sources technical candidates for engineering and other roles, partnering with recruiters and hiring managers to build talent pipelines. Develops sourcing strategies, uses competitive intelligence and funnel metrics to advise hiring decisions, manages searches, and operates HRIS and ATS systems to review applicants, generate reports, and track performance. This temporary remote role runs through the end of 2026 and supports teams across the United States and Canada.

Lead cyber incident response engagements from scoping through recovery across multi-system environments. Coordinate claims teams, breach counsel, forensic providers, policyholders, and other stakeholders; oversee investigations, manage timelines and scope creep, translate forensic findings for technical, legal, and executive audiences, and handle legally sensitive materials. The role also contributes to incident response methodologies, playbooks, and tooling.

The Accounting Manager oversees full-cycle accounting, month-end close, revenue recognition, AP, inventory, fixed assets, payroll, cash management, reporting, audits, tax compliance, and internal controls. The role will improve accounting processes through AI workflows, automation, ERP capabilities, and scalable controls. This position partners with Finance and business stakeholders on analysis, budgeting, KPIs, and accounting insights while supporting organizational growth and future SOX readiness.

Full-time remote engineering internship with Product Engineering and AI/ML Engineering tracks. Interns may build and optimize scalable product features, contribute to architecture and design decisions, develop data pipelines and machine learning models, deploy AI applications, and integrate LLM-powered capabilities into Chess.com products. Applicants should be enrolled students or equivalent bootcamp participants with strong communication, ownership, teamwork, and relevant programming, database, machine learning, or AI experience.