Top Tech Jobs & Startup Jobs in Chicago, IL

Provides senior legal counsel on technology, product development, data privacy, governance, licensing, cybersecurity, and responsible AI. Advises Product and Engineering teams throughout the product lifecycle, leads privacy compliance, negotiates SaaS and technology agreements, manages privacy vendors, and partners with Procurement on contract lifecycle processes. Balances legal, business, policy, and reputational risks while advising senior stakeholders and counterparties.

Coordinates strategic AI programs across engineering, product, legal, risk, compliance, security, HR, and business teams. Develops execution plans, governance frameworks, status reporting, risk registers, and executive communications. Supports AI platform and agent deployment initiatives, AI policy development, enterprise training, stakeholder alignment, and adoption. Requires strong program management, AI technology understanding, organizational skills, and experience managing complex cross-functional initiatives.

Lead the design and delivery of production AI systems, agentic workflows, and shared AI platform capabilities for loan origination and servicing. Responsibilities include model selection and routing, MCP and agent interfaces, RAG and context engineering, evaluation and observability, reliability practices, and scalable backend architecture. The role operates independently on complex initiatives, establishes technical patterns, makes platform decisions, and mentors engineers.

Leads the discovery, prototyping, development, and production deployment of AI-powered workflow products. Partners with business, engineering, security, legal, procurement, and executive stakeholders to identify automation opportunities, define requirements, prioritize initiatives, measure business outcomes, and establish governance documentation. Requires hands-on experience with modern AI technologies, agentic workflows, LLMs, prompt engineering, and RAG, plus regular travel to company offices and field locations.

Drive the WDSuite product roadmap for an affordable equity platform. Translate user and business needs into product strategies, requirements, user stories, and prototypes; serve as Product Owner for scrum teams; collaborate with engineers, stakeholders, customers, and partners; gather feedback; prioritize capabilities; and guide products from concept through delivery.

Lead Data Engineer responsible for defining architecture, engineering standards, and best practices for the enterprise data platform, collaborating with distributed teams for modernization and scalability.