Top Tech Jobs & Startup Jobs in Chicago, IL

Leads corporate strategy and transformation initiatives supporting senior leadership, growth, affordability, technology-enabled operating model changes, and strategic implementation. Oversees complex projects, business cases, cost-benefit analyses, budgets, resource allocation, and multiple priorities. Develops insights from quantitative and qualitative analysis, advises executives, collaborates across a matrixed organization, and leads and develops direct reports.

Associate General Counsel providing legal advice on regulatory, business, operational, litigation, examination, and administrative matters for a health insurer. The role supports business leaders, manages legal risks, represents the company before regulators and government agencies, coordinates litigation, advises on legal projects, and collaborates across legal and business functions. The position requires a Juris Doctor, state bar license, and eight years of attorney experience, preferably including healthcare or insurance regulatory and litigation experience.

Leads strategic financial analysis, forecasting, reporting, budgeting, scenario planning, ROI evaluations, financial modeling, and decision support for IT and Customer Service leadership. Develops dashboards, management presentations, business cases, and cost transparency initiatives; oversees labor and non-labor utilization, vendor governance, procurement support, financial close activities, and monthly reporting. Partners across Finance, Procurement, and business teams while maintaining compliance and data integrity.

Develops and executes learning strategies aligned with business goals, analyzes performance and learning gaps, recommends and evaluates solutions, and manages complex instructional initiatives. Builds consultative relationships with internal clients, coaches team members, coordinates communication and project activities, and supports instructor-led, web-based, and blended learning programs. Applies adult learning theory, instructional design practices, analytical reasoning, and performance consulting to improve learning and business outcomes.

The Staff Actuary performs pricing, underwriting, reserving, forecasting, statistical analysis, and financial modeling. The role evaluates business decisions using actuarial and financial principles, communicates complex findings and recommendations, and may manage small actuarial projects. Required qualifications include an actuarial or related bachelor’s degree, ASA designation, MAAA membership, and at least three years of actuarial experience.

Creates user-centered product and UX designs based on research and design principles. Collaborates with product teams, stakeholders, and design peers to deliver engaging desktop and mobile experiences, prototypes, and design solutions. Responsibilities include applying human-centered design, communicating design decisions, incorporating feedback, supporting usability testing, and managing stakeholder expectations.

Manages software engineering services, projects, resources, delivery performance, capacity planning, budgets, vendors, and distributed teams. The role partners with business and technical stakeholders to align IT resource requirements with strategic goals, oversee Agile software development, optimize engineering productivity, and support technology platforms including cloud and SaaS solutions.

Leads development of functional and non-functional business requirements, translates business strategy into product requirements, and partners with business solutions leads. Builds cross-functional relationships, manages multiple projects, mentors staff, and supports product development, launch, monitoring, and improvement. The role requires business and financial analysis, market knowledge, communication, facilitation, and project management skills. Healthcare, digital health product, benefits consulting, and metabolic health experience are preferred.

Provides executive transparency and financial analysis for sub-portfolios, reviewing spending, financial health, strategic alignment, prioritization, funding, and execution. The role requires portfolio and project financial management, business case development, benefit realization, resource management, customer relationship management, negotiation, and communication skills. It uses Planview or comparable portfolio management tools and Microsoft products in a hybrid, three-days-in-office environment.

Gathers and analyzes data from multiple systems, develops and executes ongoing reports, prepares business and block experience analyses, disseminates information, supports cross-departmental projects, resolves issues, assesses operational impacts, and recommends solutions while handling confidential information.