Top Tech Jobs & Startup Jobs in Chicago, IL

Analyzes personal lines insurance and digital product performance using SQL, BI tools, statistical methods, and financial modeling. Partners with product, experience, actuarial, finance, and operations teams to identify growth opportunities, optimize digital customer experiences, assess risks, support business cases, and influence leadership decisions. Applies AI and automation to improve analytical efficiency, communicates insights through presentations and reports, and mentors colleagues.

Leads the People Systems and Workforce Insights function, setting HR technology strategy, roadmap, governance, budgets, and vendor priorities. Oversees Workday configuration, integrations, security, reporting, data governance, compliance, and system improvements. Directs workforce analytics, executive reporting, employee listening, self-service insights, and responsible AI use. Advises senior leaders on workforce strategy, technology investments, risk, privacy, equity, and employee trust while developing teams and managing cross-functional initiatives.

Leads commercial auto actuarial pricing initiatives, manages and develops actuarial analysts and consultants, reviews analytical work, oversees project delivery, and supports business decisions. Builds internal and external client relationships, presents pricing recommendations, manages team workloads, and performs hiring, performance evaluation, coaching, and employee development. Requires commercial insurance actuarial experience, ACAS certification, leadership skills, and expertise in commercial auto pricing.

Lead enterprise data, ontology, cloud, and AI architecture across Palantir, Snowflake, and AWS. Define data models, governance, integration standards, platform roadmaps, and responsible AI patterns. Oversee Palantir Foundry and AIP ontology architecture, event-driven and API integrations, and AI/GenAI workflows. Lead architecture reviews, establish reusable standards, guide engineering teams, develop executive-level business cases, and align technology investments with business outcomes.

Leads commercial insurance actuarial reserving, including monthly booking and quarterly reserve reviews, reserve analysis, senior leadership communication, process improvement, and project oversight. Manages, trains, coaches, and evaluates actuarial staff; allocates workloads, supports recruiting and performance management, and collaborates with internal and external business partners. Requires strong actuarial expertise, leadership, communication, and decision-making skills.

Senior attorney responsible for structuring, drafting, and negotiating complex insurance distribution, reinsurance, and commercial transactions. Advises on multi-party insurance programs, fronting arrangements, deductible and collateral structures, MGA relationships, claims administration, and service agreements. Partners with business teams to translate novel models into effective legal and commercial frameworks, while contributing to general commercial contracts, intellectual property, marketing matters, and legal process improvement.

Lead development of internal economic capital modeling for P&C insurance, including stochastic risk models, capital allocation, stress testing, model governance, and business decision support. Partner with actuarial, reinsurance, investments, catastrophe modeling, FP&A, and enterprise risk teams. Build controlled, reproducible processes and communicate quantitative findings to business leaders, regulators, rating agencies, and management.

Leads enterprise workflow reinvention and systems-of-work design across business and technology teams. Designs human-AI collaboration, automation opportunities, controls, decision paths, and implementation-ready workflow artifacts. Facilitates senior stakeholder workshops, connects business intent to architecture and delivery, promotes reusable enterprise patterns, and helps establish systems design practices. Measures engagement impact through business outcomes, case studies, and executive storytelling.

Prepare and coordinate actuarial analyses for commercial auto pricing, including individual account pricing and portfolio ratemaking. Perform statistical modeling, document assumptions, communicate findings to technical and non-technical audiences, collaborate cross-functionally, mentor junior staff, and develop new rating and reserving methodologies.