Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Extend’s regulatory compliance strategy for service contract and insurance programs across North America. Oversees licensing, regulatory examinations, audits, filings, terms and conditions, internal controls, reporting, and compliance governance. Advises executive leadership, regulators, auditors, and cross-functional teams; builds and develops the compliance organization; establishes KPIs; manages regulatory relationships; and modernizes compliance processes using AI and technology.

Evaluate and adjudicate complex product and shipping protection claims, investigate fraud and unusual claim patterns, manage escalations, and ensure decisions comply with policies. Communicate with customers, service providers, and internal teams by phone and email; coordinate technician dispatch and parts ordering; document interactions; troubleshoot system issues; recommend process improvements; and support training and service-quality initiatives.

Develop revenue optimization and risk mitigation strategies using experimentation, causal inference, forecasting, Monte Carlo simulations, and machine learning. Build data pipelines, improve analytics infrastructure, generate insights for client-facing teams, and influence Product and Engineering roadmaps. The role requires strong strategic thinking, business impact orientation, and collaboration in a remote-first environment.

Analyze behavioral, transactional, and interaction data to identify fraud patterns and emerging threats. Develop monitoring frameworks, dashboards, and mitigation solutions; evaluate AI fraud-review decisions; and translate findings into prompt, rule, workflow, and machine-learning feature improvements. Collaborate with Fraud Operations and Machine Learning teams, participate in code reviews, and mentor junior analysts. The role requires strong SQL and Python skills, statistical analysis expertise, business judgment, and fraud analytics experience.

Build and ship full-stack fulfillment features covering refunds, replacements, reverse logistics, and servicing. Own features from design through deployment, release, and monitoring while developing scalable event-driven and AI-native applications. Build single-page applications, collaborate with designers and cross-functional teams, apply sound API and data modeling practices, and deliver AI/agentic features safely in production. Identify technical investments, communicate tradeoffs, and work independently through ambiguous problems.

Analyze merchant and product data to create business cases, pricing models, ROI analyses, reporting, and financial narratives. Partner with Sales, Merchant Success, Product, and Engineering to support merchant acquisition, expansion, renewals, product improvements, and roadmap development. Engage directly with consumer brands to understand reporting needs and communicate complex insights to technical and non-technical audiences.

Lead and manage a remote analytics engineering team responsible for Extend’s Snowflake warehouse, dbt repository, ingestion pipelines, data models, monitoring, and quality standards. Oversee hiring and development, architecture, platform migrations, reliability, incident response, documentation, and self-service analytics. Partner with actuarial, risk, fraud, product, finance, and operations teams to establish trusted shared data definitions and prioritize platform improvements.

Manage growth strategy and strategic relationships for Extend’s largest enterprise merchants. Responsibilities include optimizing account performance, conducting executive business reviews, driving product adoption, managing promotional budgets, developing long-term business plans, and identifying ROI opportunities through data. The role also gathers customer feedback for product roadmaps and collaborates with risk, analytics, marketing, product, and operations teams. Travel to client sites is estimated at 15–20%.

Build and maintain invoicing, reimbursement, revenue recognition, claims, and financial reporting models using SQL and dbt. Reconcile merchant, operational, warehouse, and accounting data; investigate variances; validate expenses; and establish automated financial controls. The role also triages data issues, investigates production APIs, supports audits, partners on merchant configuration, and drives upstream fixes through root-cause analysis and automation.

Leads financial systems engineering for a service-contract business. Owns reconciliation systems, invoicing logic, financial data models, revenue recognition controls, and audit reporting. Manages SQL and dbt models, automated validations, exception resolution, merchant configuration audits, and cross-functional escalations across Engineering, Finance, Accounting, and Revenue teams. Leads individual contributors and develops the team as business needs evolve.