Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the technical direction, architecture, and development of Compass, an LLM-powered agent platform. Design multi-agent systems, MCP and A2A integrations, orchestration, evaluation, and observability infrastructure. Drive cross-team technical projects, production support, engineering quality, mentoring, and adoption of AI-assisted development practices. Partner with Product, QA, Design, Operations, and Engineering stakeholders to deliver reliable agentic systems.

Lead Runpod’s accounting organization and strategy, overseeing financial close, US GAAP reporting, technical accounting, audits, controls, tax, compliance, equity accounting, and accounting systems. Build and develop the team, establish SOX readiness, partner with executives and investors, and support financings and strategic transactions. Drive automation and AI across accounting workflows while ensuring the function is scalable, accurate, and audit-ready.

Owns the end-to-end redemption and fulfillment pipeline, including vendor SLAs, shipping, exceptions, customer support processes, and cost reconciliation. Manages the product catalog, sourcing, merchandising, pricing, vendor onboarding, and market data integrations. Establishes cross-functional operating rhythms, reporting, decision rights, and scalable processes while building a future fulfillment and merchandising team.

Manage commercial print partners across performance, capacity, cost, and contract compliance. Run scorecards and business reviews, audit invoices and recover overcharges, forecast capacity, enforce print and postal standards, and coordinate corrective actions. The role also qualifies new partners, supports production rerouting, and builds AI- and SQL-driven automation for audits and reporting. It requires extensive collaboration across operations, logistics, Product, Engineering, Finance, and Supply Chain, with approximately half the time spent onsite at partner facilities.

Leads East Coast enterprise sales performance, coaching and developing quota-carrying sellers, managing complex multi-stakeholder deals, improving forecasting and pipeline discipline, recruiting talent, and driving regional go-to-market execution. Partners with senior executives and cross-functional teams to achieve predictable revenue growth across senior living and post-acute markets. Requires extensive enterprise B2B SaaS sales leadership experience, MEDDPICC expertise, and willingness to travel 40–50%.

Own QA strategy and release quality for POS, back-office, and payments products. Build automated unit, integration, API, contract, and end-to-end tests; integrate testing into GitHub Actions; validate hardware, offline modes, payment flows, and upgrades; establish release gates and test environments; monitor quality metrics; reproduce merchant issues; and coach engineers on testable design and quality practices.

Own the full enterprise sales and customer success cycle for large Fortune 1000 accounts. Prospect, sell, renew, and expand cybersecurity platform relationships while engaging security and engineering executives. Build complex account plans, manage channel ecosystems, collaborate with internal teams, forecast opportunities, and drive million-dollar-plus ARR transactions. Success requires enterprise technical sales experience, cybersecurity or DevSecOps domain knowledge, executive presence, consultative selling, and a track record of exceeding quota.

The Channel Leader drives Zerigo Health's channel strategy through partner relationships, facilitating sales, managing account health, and ensuring growth.

Provide tax preparation, planning, and advisory services for individuals and businesses holding bitcoin and digital assets. Prepare and file tax returns, calculate cost basis and gains/losses, advise on mining/staking/airdrop income, collaborate with advisors and estate planners, maintain compliance documentation, and contribute thought leadership through articles and webinars.

Own a portfolio of clients to maximize retention and growth: run client calls, analyze lead and performance data, spot retention risks and upsell opportunities, coordinate internal teams to deliver on strategy, and contribute process and AI-driven improvements to internal systems.