Top Tech Jobs & Startup Jobs in Chicago, IL

Provide internal IT support and endpoint management for a fully remote workforce: provision and maintain macOS/Windows devices, enforce endpoint security, manage MDM/UEM and SaaS provisioning (Google Workspace, Slack, Atlassian), triage help desk tickets, maintain IT documentation, oversee vendor/licensing relationships, and partner on internal infrastructure and policy initiatives including AI tool governance.

Remote short-term contract to review, label, classify, and validate text data for LLM training. Follow detailed guidelines, ensure accuracy and consistency, identify edge cases, perform quality checks, and meet productivity standards while working independently.

Lead design, development, and administration of application interfaces, APIs, and secure file transfers. Administer GoAnywhere MFT, manage Windows/Linux servers, support Azure hybrid integrations, troubleshoot network connectivity, provide technical leadership, establish integration best practices, and mentor team members to deliver secure, compliant solutions.

Lead cloud and integration architecture end-to-end for production AI systems: design secure AWS-hosted services, define integration contracts and patterns, guide implementation, unblock developers, coordinate with client architects and vendors, maintain architecture governance and delivery progress.

Lead client workshops and discovery to map current/future-state processes, translate business needs into functional requirements and user stories, and produce clear process documentation. Partner with technical leads to hand off specs, use AI tools to accelerate deliverables, and travel onsite several times per quarter to support workshops and key milestones.

Lead end-to-end CMMC implementations, translating requirements into actionable plans, coordinating internal and external stakeholders, guiding customers on CUI/FCI handling, SSPs and POA&Ms, evidence collection, remediation tracking, and readiness. Build repeatable playbooks, deliver training, improve handoffs, and feed product and process insights back to the organization.

Lead strategy and execution for savings, money market, and CD products. Own product roadmaps, P&L, A/B testing, metrics, vendor relationships, and cross-functional delivery. Use data-driven insights to drive acquisition, retention, and feature enhancements while mentoring stakeholders and ensuring member-focused product outcomes.

Provide administrative support across multiple entities: manage vendors and purchases, maintain office presentation, plan events, use CRM and eFiling, manage DocuSign templates, update internal charts, assist sales/marketing and perform executive-assigned duties.

Conduct research to evaluate and improve forecasting and agentic LLM web research. Formulate open problems, devise innovative solutions, build evaluations, benchmarks, and datasets, publish findings, and collaborate with frontier labs to improve AI epistemics and decision-making.

Develop and grow strategic partnerships with ISVs, agencies, and consultancies to generate pipeline and revenue. Create joint go-to-market plans, execute co-sell strategies with Sales, lead commercial negotiations, define partner success metrics, and collaborate cross-functionally to embed partners into enterprise priorities.