Top Tech Jobs & Startup Jobs in Chicago, IL

Own and operate the AI-native platform runtime including Kubernetes (GKE), Terraform, GCP, CI/CD, observability, orchestration (Temporal, Kong). Improve reliability, performance, cost, multi-tenant provisioning, developer experience, and lead on-call and incident response.

Build intuitive, high-performance React interfaces for AI-powered insurance workflows. Collaborate with design and backend teams, create reusable UI components and design systems, integrate frontend features with AI services (document review, entity extraction, quote comparison), rapidly prototype, and iterate based on user feedback.

Lead the product roadmap for data ingestion, enrichment, and pipelines. Define integrations with PDFs, portals, APIs, spreadsheets, and carriers. Partner with AI and engineering to build scalable workflows for cleaning, validating, mapping, and enriching data. Work with customer-facing teams to remove adoption blockers, prioritize initiatives, prototype solutions, and ship frequent improvements.

Lead discovery and delivery of AI-enabled workflow features for insurance operations. Work closely with users, engineering, and GTM to design scalable workflows, measure adoption and impact, support pilots/betas, and iterate to build trusted AI-driven products.

Work directly with insurance customers to deploy and configure AI-powered workflows, integrate with agency management systems and messy customer data, debug integrations, build tooling, and relay product requirements to the core platform while partnering with sales and customer success.

Serve as a core operating partner to Head of Finance & Strategy, building financial models, reporting rhythms, dashboards, AI-driven workflows, investor/board reporting, and driving cross-functional operational initiatives from analysis through execution.

Own internal IT systems: identity/SSO provisioning, device lifecycle and MDM/endpoint security, SaaS access and licensing, onboarding/offboarding, automation of IT workflows, internal networking, and support while contributing to security and compliance.

Partner with Head of Finance & Strategy to lead cross-functional, high-priority initiatives. Build reporting rhythms, financial models, dashboards, processes, and AI-driven automations. Support board and investor reporting, drive execution across finance, GTM, ops, and product analytics, and create structure in ambiguous areas at a high-growth, remote-first insurtech.

Own post-sale customer journey for Employee Benefits agencies: onboard, drive adoption, maintain relationships, manage retention and expansion, translate feedback into product insights, and build scalable onboarding and training materials.

Design and own end-to-end data platform architecture, build ingestion and transformation pipelines, model multi-tenant datasets, optimize Postgres and ClickHouse performance/cost, implement orchestration and observability, define data quality and reconciliation standards, and mentor data/product engineers.