Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale a multi-market restoration sales organization as a hands-on player-coach: hire and ramp reps, enforce CRM and pipeline discipline, build channel-specific playbooks, personally pursue large commercial and national accounts, align marketing with sales, and provide forecasting and performance reporting to ownership.

Lead design and implementation of backend services and distributed systems for real-time AI automation. Build scalable, observable microservices, streaming data pipelines, and async event-driven architectures. Collaborate across frontend, product, and DevOps to ensure performance, reliability, and seamless integration at scale.

Serve as liaison between HR stakeholders and technical teams to elicit, document, and translate business requirements into Workday solutions. Support Workday functional areas (payroll, benefits, timekeeping, recruiting, talent), assist with integrations, reporting, releases, UAT, process improvement, and stakeholder engagement to align solutions with university policies and goals.

Own the support inbox for self-published authors, guide onboarding to first wins, maintain help docs and tutorials, handle billing/account questions, identify recurring friction and deliver prioritized product feedback, and build lightweight support processes to scale quality.

Lead the supply side of an early-stage two-sided marketplace: recruit and retain partner businesses and contributors across verticals and geographies, own geo rate cards, capacity forecasting, contributor experience (onboarding, payments, support), and partner with platform on self-serve tooling. Close partners directly and optimize pricing, economics, and systems for scale.

Own and operate the realtime voice stack and call-data platform end-to-end: telephony/WebRTC integration, streaming STT/TTS, realtime voice agents, call-to-transcript pipelines, data warehousing, analytics, and dashboards. Build AI-native workflows, RAG/search, human-in-the-loop flows, and optimize performance, latency, and cost. Mentor teammates and collaborate across product and subject-matter experts.

Manage special-handling past-due commercial accounts including disputes, fraud, and bankruptcy. Investigate cases end-to-end, communicate with merchants and partners, log bank-compliant documentation, prepare collection notices, and keep accounts audit-ready while supporting broader collections tasks.

Lead engineering of core scheduling and orchestration subsystems for an orbital edge compute platform. Own an MVP for autonomous scheduling across compute node fleets, scale to larger satellite fleets with data sovereignty, design performant and reliable distributed engines, build scheduling and workload-placement logic for intermittent-connectivity edge environments, and provide technical leadership while partnering with cross-functional teams to deliver secure, customer-focused solutions.

Lead product strategy, planning, and delivery for RPA, AI, and technology initiatives. Define requirements, roadmaps, success metrics, and ROI. Coordinate cross-functional teams, manage multiple projects, mitigate risk, support change management, and ensure projects deliver on scope, schedule, and budget.

Own the full enterprise sales cycle for large, complex accounts: prospecting, managing multi-stakeholder deals, running technical proofs-of-concept with engineering, refining enterprise sales plays, and feeding customer insights to product and leadership to drive repeatable revenue.