Top Tech Jobs & Startup Jobs in Chicago, IL

Manage employee questions and HR support, leaves of absence, benefits administration, HRIS operations, compliance, reporting, policies, and internal People Ops resources. Plan offsites, virtual events, and culture initiatives for remote and hybrid teams. The role partners with brokers, carriers, leave providers, and internal stakeholders while continuously improving processes and employee experience.

Lead identification, scoping, and delivery of production AI features and automation. Prototype and ship LLM-powered solutions, build RAG and agentic pipelines, create low-code workflows, integrate AI into existing systems, and partner cross-functionally to prioritize, deploy, monitor, and iterate on AI initiatives across product, operations, and business teams.

As a Homeowner Advisor, educate homeowners about equity investment products, manage inquiries, and guide them through the funding process while achieving uncapped commissions.

Run intake, triage, and enablement between product/engineering and operations. Reproduce and route validated issues, build enablement and adoption programs, instrument feedback loops, and extend tooling and processes to scale delivery and measure impact.

Own product management for the homeowner journey (acquisition funnel, application, portal, post-origination). Run sprint planning, write specs, ship with design and engineering, run experiments to improve conversion, diagnose funnel drop-off, support state-specific launches, and conduct discovery with homeowners and partners to inform the roadmap.

Own product management for the Salesforce-based business platform powering underwriting, servicing, funding, and compliance for a 140+ person ops org. Run intake, write specs, prioritize and sequence backlog with a Salesforce engineering team, manage bi-weekly sprints and rollouts, define success metrics (cycle time, throughput, error rates), and coordinate enablement, instrumentation, and adoption tracking with cross-functional partners.

Provide primary legal support for the end-to-end home equity origination lifecycle, advising on federal and state consumer finance regulation, UDAAP and fair lending, privacy (GLBA/CCPA), and transactional agreements. Review marketing and product materials, manage litigation and consumer disputes, coordinate outside counsel, and partner cross-functionally to scale origination processes and ensure compliance as the business grows.