Top Tech Jobs & Startup Jobs in Chicago, IL

Lead growth strategy and roadmap development for healthcare subscription products. Own the acquisition funnel from discovery through conversion, activation, and retention handoff. Define value propositions, KPIs, experimentation practices, and growth models while partnering with Analytics, Design, Research, Engineering, Marketing, and CRM teams. Use quantitative and qualitative insights to prioritize opportunities, deliver scalable subscription capabilities, and balance consumer value with business, privacy, compliance, and operational considerations.

Leads AI/ML engineering teams across platform and delivery pods, managing employees and contractors while enforcing code, agent, review, and production-readiness standards. Partners on reusable templates, pipelines, and evaluation processes, ensures adoption across teams, manages contractor performance and conversion, and removes delivery blockers. The role requires hands-on credibility reviewing agent architectures, prompts, and evaluation suites, with experience operating as a player-coach in fast-moving organizations.

Lead enterprise AI platform automation across infrastructure provisioning, CI/CD, governance, observability, deployment, and lifecycle management. Build self-service capabilities for GenAI, data science, data engineering, and analytics workloads using Terraform, Kubernetes, cloud technologies, Python, and DevSecOps practices. Support agentic AI, event-driven architectures, distributed computing, and operational reliability while collaborating with engineering, architecture, governance, security, and business stakeholders. Provide technical leadership, design reviews, mentoring, and best-practice guidance.

Build and deploy LLM-powered agents, workflows, and production integrations using platform templates, pipelines, and guardrails. Develop and run evaluation suites, integrate business systems and data sources, instrument cost and quality telemetry, and collaborate with business users to iterate within bounded scopes. The role requires strong Python and TypeScript, API development, prompt and context engineering, and production experience with agents, RAG, and tool use.

Build and deploy LLM-powered agents and workflows using templates, pipelines, and guardrails. Develop comprehensive evaluations, integrate AI solutions with business systems and data sources, and instrument applications for cost and quality telemetry. Collaborate with business users to iterate within defined scopes. The role requires strong Python and TypeScript skills, production experience with LLM applications, API development, prompt and context engineering, retrieval, and healthcare data handling.

Design, build, and optimize enterprise ETL/ELT pipelines, cloud data lakes, lakehouse solutions, data models, and semantic layers across AWS and Azure. Ensure data quality, security, performance, reliability, and governance while supporting analytics, reporting, and AI initiatives. Collaborate with product, engineering, IT, and business stakeholders to translate requirements into scalable data solutions, monitor pipeline health, troubleshoot issues, and improve data architecture and practices.

Lead end-to-end product design for client engagements: discovery, UX architecture, high-fidelity UI, interactive prototypes, and design systems. Conduct lightweight research and usability testing, facilitate workshops and design sprints, collaborate with cross-functional teams in agile delivery, support pre-sales scoping, and mentor junior designers.

Lead end-to-end product delivery for large-scale banking and financial-services transformations. Manage requirements and roadmaps, liaise between stakeholders, compliance, and engineering, and architect modern payment workflows (RTP, FedNow, ISO20022). Guide core banking modernization and cloud-native/open banking architectures, ensure regulatory compliance, champion AI/LLM-driven efficiencies across delivery artifacts, and operate in agile, client-facing engagements with sales/pre-sales responsibilities.

Own and grow Hi‑Tech sector pipeline: build new‑logo opportunities, advance deals from intro to close, expand existing accounts, and provide competitive sector intelligence to leadership.

Lead cross-functional teams to define and evolve platform and application architecture, introduce new technologies and best practices, solve cross-team technical challenges, guide global cloud and regulated (FedRAMP) deployments, and mentor engineers while driving engineering quality, observability, and production readiness.