Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Manage the company’s IT department and ensure reliable operation of networks, servers, systems, security, and end-user technology. Responsibilities include AWS and Oracle administration, Microsoft 365 access management, technical support, cybersecurity monitoring, compliance, vendor coordination, budgeting, and leading IT infrastructure projects. The role also supports Windows and Apple devices, manages IT tickets, and coordinates cross-functional technology initiatives.

Designs and manages training initiatives for behavioral health providers. Responsibilities include conducting needs analyses, applying instructional design models, translating clinical protocols into scenario-based learning, developing Articulate 360 courses and multimedia, using generative AI responsibly, creating assessments, performing quality assurance, analyzing feedback, and managing project timelines.

Designs and delivers production-grade enterprise AI solutions using LLMs, RAG, agentic AI, MCP, and Azure. Translates business needs into secure, scalable architectures; establishes AI engineering standards, evaluation, observability, and guardrails; leads architecture and code reviews; mentors AI, software, and data engineers; evaluates emerging technologies; and supports client workshops, demonstrations, solutioning, and presales.

Build and deploy production-grade generative and agentic AI applications using Python or JavaScript/TypeScript, LangChain, LangGraph, RAG, vector databases, Docker, Kubernetes, and cloud platforms. Develop workflows, integrations, evaluation pipelines, observability, security controls, and CI/CD processes. Optimize quality, performance, reliability, and cost while supporting production operations. Collaborate with architects, engineers, security teams, customers, and stakeholders; create documentation, participate in reviews, mentor engineers, and communicate technical tradeoffs.

Leads complex security investigations from detection through resolution, including threat analysis, containment, eradication, recovery, root cause analysis, threat hunting, vulnerability management, and attack-chain reconstruction. Develops incident response playbooks and SOPs, writes executive reports, mentors Tier I analysts, and participates in on-call coverage. Requires advanced Windows, networking, scripting, malware analysis, SIEM, digital forensics, and incident response capabilities.

Performs cloud security engineering across AWS and GCP, including system hardening, patching, vulnerability remediation, compliance scanning, security tool management, incident response, and cloud operations. Troubleshoots Linux, Windows, network, application, and identity issues; supports FedRAMP, FISMA, and NIST 800-53 requirements; documents procedures and incidents; contributes to automation; mentors junior engineers; and participates in a 24×7 on-call rotation.

Supports and improves IT infrastructure across multi-site healthcare centers, including endpoints, networks, cloud systems, printing, AV, phones, digital signage, SaaS applications, Microsoft 365, and Entra ID. Delivers site and technology projects, automates onboarding and offboarding, troubleshoots escalated issues, manages vendors, supports disaster recovery testing, and maintains documentation, security, asset inventories, and HIPAA-compliant access practices.

Own a Chicago sales territory for SumUp by prospecting local businesses, managing the full sales cycle, demonstrating payment and loyalty solutions, negotiating, closing new business, and maintaining pipeline activity in Salesforce. The role requires face-to-face merchant engagement, territory research, relationship building, and frequent local travel using reliable transportation.