Top Tech Jobs & Startup Jobs in Chicago, IL

Own the enterprise test automation strategy, scale a Playwright and JavaScript framework, expand coverage across Salesforce, MuleSoft, D365, and reporting systems, and build scalable execution and reporting infrastructure. Design QA standards, metrics, and review processes while developing AI-powered agents with Cursor for performance testing, regression analysis, and defect triage. Partner with engineering, product, business, and AI platform teams to deliver governed, reusable quality tooling.

Leads and performs assurance reviews of insurance members, evaluating underwriting, documentation, compliance, reporting, financial activities, rates, forms, and policy files. Identifies risks, recommends corrective actions, monitors remediation, analyzes data for sampling, reviews premium trust transactions, and tracks insurance regulatory changes. The role also supports review methodology development and maintains relationships with members and senior management.

Owns day-to-day captive insurance relationships and end-to-end operational execution after deals bind. Responsibilities include coordinating reinsurance agreements, establishing trusts and letters of credit, monitoring premiums and loss settlements, onboarding captives, supporting regulatory and domicile requirements, resolving operational issues, reporting portfolio performance, and improving scalable processes across Legal, Treasury, Operations, Actuarial, and Finance.

Leads strategic planning, budgeting, forecasting, and financial analysis for the risk exchange platform. Partners with finance, accounting, actuarial, and distribution teams; analyzes operational and insurance results; prepares management reporting; supports monthly close; and presents insights to senior leadership. Drives Pigment planning-platform adoption and improves FP&A processes through AI, automation, documentation, and digital tools.

Manage onboarding, policy administration, and bordereaux workflows; ensure data integrity and SLA adherence; produce reports using Snowflake, Power BI, and Excel; collaborate cross-functionally to document SOPs and implement process improvements.

Design, build, and operate scalable web applications, APIs, services, and AI-enabled workflows. Use AI tools across the development lifecycle, ensure reliability, performance, and observability, contribute to technical decisions, iterate from user feedback, and own production quality and delivery as part of cross-functional squads.

Lead discovery, roadmap, and delivery of data platform capabilities for the Accelerant Risk Exchange. Define strategy, prioritize ingestion/consumption features, collaborate with stakeholders and engineering, champion AI-native experimentation, and communicate outcomes to internal and external partners.

Build and validate production-grade ML and AI systems across pricing, underwriting, claims, and portfolio management. Work with structured and unstructured data, LLMs and agentic workflows, extract information from documents, resolve entities, create feature pipelines and inference services, quantify uncertainty, monitor drift, and measure business impact in collaboration with engineers, actuaries, underwriters, and product teams.

Design, implement, and operate secure, scalable multi-cloud infrastructure (Azure/AWS) with IaC (Terraform), managed Kubernetes, containers, and AI platform support. Lead complex projects, define operational processes, ensure security/compliance, mentor teammates, and maintain observability for production systems.

Lead reliability and observability for the financial data platform: define SLOs/SLIs, build metrics pipelines, extend instrumentation across Velocity, Redpanda, MuleSoft, Snowflake, Fabric, and AWS; implement incident management (Datadog -> Incident.io -> ServiceNow), scale automation and remediation, and design AI-assisted SRE agents using Cursor for triage and root-cause analysis.