Top Tech Jobs & Startup Jobs in Chicago, IL

Lead a team to design, build, modernize, and operate secure, scalable hybrid infrastructure across cloud and on-premises. Own infrastructure strategy, IaC automation, platform delivery, standards, vendor management, operational readiness, and cross-functional partnerships to ensure resilient, observable, and supportable enterprise platforms.

Plan, coordinate, and execute B2B events (conferences, tradeshows, hosted and partner events) end-to-end. Partner with marketing, sales, and customer success to define strategy, manage vendors and budgets, oversee registration and on-site logistics, track performance and ROI, and maintain event documentation and systems like Monday.com and Salesforce.

Lead accounting oversight for multiple divisions ($47M combined sales). Manage AP/AR/collections teams, month-end close, intercompany reconciliations, audits, financial reporting, budgeting, cash management, and process improvements while ensuring US GAAP compliance.

Full-cycle recruiter responsible for sourcing, screening, and closing sales candidates. Partner with leadership to define hiring needs, manage multiple high-priority roles, lead compensation discussions, track recruiting metrics, and improve processes while delivering a strong candidate experience.

Embed with enterprise customers to design, build, and deploy production-grade integrations and data pipelines. Own technical discovery, end-to-end integration lifecycle, AI agent orchestration, customer technical relationships, and feedback to product and engineering. Produce runbooks, templates, and durable handoffs.

Design and implement large-scale product features, build and optimize backend systems and APIs, deploy via cloud and CI/CD, maintain secure reliable code, troubleshoot production issues, conduct code reviews, mentor teammates, and develop client relationships to drive digital outcomes.

Lead full-cycle recruiting for technical and non-technical roles, build creative sourcing strategies for niche profiles, deliver exceptional candidate experience, run and optimize Greenhouse, leverage AI (Claude) across the funnel, partner with hiring managers, use pipeline data to improve time-to-fill, and help grow employer brand in collectibles, fintech, and marketplace communities.

Partner with sales to drive enterprise pre-sales engagements: architect and demonstrate solutions, run proof-of-value evaluations, uncover technical/business requirements, and manage technical aspects through the sales cycle.

Contract fractional HR generalist to own HR operations: payroll and HRIS (Rippling), benefits administration, compliance, systems automation and documentation, onboarding/recruiting support, and vendor coordination. Expected ~15 hrs/week for an initial 6-month engagement, with deliverables and system audits in the first 90 days.

Sell Litify's AI-driven legal operating platform to law firms and legal departments. Manage full upsell motions, consult on AI adoption, deliver high-level demos to C-suite, meet sales targets, and articulate ROI of autonomous agents and AI integrations.