Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct continuous manual penetration testing across network, web application, cloud, and social engineering attack surfaces. Pursue findings through post-exploitation, lateral movement, privilege escalation, and business-impact validation. Communicate results to technical and non-technical clients, lead debriefs, improve team tooling, direct AI and automation, mentor junior testers, and collaborate with R&D to operationalize repeatable techniques.

Build and operate production AI and LLM systems for safety-critical enterprise applications. Responsibilities include multi-step agent orchestration, retrieval across Neo4j and vector stores, evaluation frameworks, model comparison, observability, quality monitoring, failure handling, and production incident response. The role requires strong Python and experience with asynchronous services, LLM workflows, evaluation, retrieval, graph reasoning, and enterprise AI security. It also contributes to model selection, technical direction, and the AI roadmap.

Owns high-visibility, cross-functional finance programs spanning quote-to-cash, systems implementations, data infrastructure, planning, M&A integration, and IPO readiness. The role translates between finance and business teams, drives programs to completion without direct authority, designs scalable processes and controls, and advances AI and automation across finance operations.

Provide in-house legal counsel for procurement, supply chain, logistics, operations and real estate across North America. Draft, review, and negotiate vendor and service agreements, manage vendor disputes and pre-litigation issues, support M&A due diligence, develop contracting templates and playbooks, and advise on operational risk, compliance, and strategic transformation initiatives.

Join Impact Scale’s ongoing talent network for potential future opportunities in growth and strategy, creative production, or technology and engineering. The company seeks affiliate managers, media buyers, campaign managers, video editors, content creators, back-end developers, and software engineers. This is a talent pipeline rather than an application for a specific immediate opening.

Build and deploy production-grade AI applications and agentic systems for client organizations. Translate ambiguous business needs into architectures, prototypes, workflows, APIs, data pipelines, and scalable products. Engineer agent harnesses, orchestration graphs, evaluations, observability, safeguards, and human controls. Collaborate directly with clients and cross-functional teams, troubleshoot complex environments, communicate technical trade-offs, and support workshops and pre-sales. Occasional travel may be required for client engagements.

Qualifies inbound leads, conducts targeted outbound prospecting, researches film and television production activity, validates marketing-qualified leads, maintains pipeline records, and supports Account Executives. The role targets production accountants, line producers, UPMs, and finance coordinators while developing entertainment industry knowledge and consultative sales skills for progression into an Account Executive position.

Own strategic enterprise customer relationships from pilot through adoption, renewal, and expansion. Build account plans, engage executive sponsors, lead business reviews, support deployments, drive commercial expansion, manage escalations, provide product feedback, and develop customer case studies. The role also helps establish the enterprise customer success playbook and requires 30–50% travel.

Own Stay AI’s marketing function end to end, including competitive positioning, product marketing, sales enablement, content, channel strategy, market narrative, pipeline generation, and executive reporting. The role partners closely with sales, product, and the CEO, creates messaging and marketing materials directly, supports product launches, analyzes campaign performance, and presents marketing results to leadership and the board.

Build and scale renewal operations for a high-volume down-market segment. Own renewal data, reporting, forecasting, pacing models, workflows, systems configuration, partner portal processes, and recurring operating cadences. Translate CRM data into executive insights, establish leading indicators, improve data quality, and coordinate with Revenue Operations, Customer Operations, IT, and cross-functional stakeholders to automate and optimize renewal processes.