Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Lead and grow regional revenue and market share across the Western US by managing and coaching a team of remote Account Executives, building executive partner relationships, executing regional sales strategies, and collaborating cross-functionally to drive partner adoption and retention. Role requires extensive travel and performance ownership.

Lead end-to-end delivery of large-scale transformational technology programs ($25M+), manage distributed matrixed teams (50+), oversee governance, financials, SOWs, contracts, risk, stakeholder engagement, and executive reporting to ensure program quality and profitability.

Lead design and implementation of scalable APIs and agent communication layers for an AI-agent driven advertising marketplace. Build high-throughput backend systems, integrate agent frameworks and adtech partners, drive architecture for authentication and protocols, mentor engineers, and prototype agent communication patterns while collaborating with product and design.

Multi-year leadership development placement reporting to the CEO, providing executive-level support, managing special projects, liaising with stakeholders, coordinating strategic communications, representing CIRI externally, and participating in ELT, Board, and Shareholder meetings. Role includes an individual development plan, mentoring, frequent travel, and placements across CIRI and subsidiaries.