Top Tech Jobs & Startup Jobs in Chicago, IL

Own the Merchant Dashboard product strategy, roadmap, information architecture, personalization, interaction patterns, and monetization surfaces. Partner with Engineering, Design, Marketing, Data Science, and go-to-market teams to deliver scalable solutions. Analyze customer feedback, market trends, data, and competitive offerings to identify opportunities, guide experimentation, and make product decisions. Advocate for merchants and communicate product vision, priorities, and trade-offs to stakeholders.

Provides Level II IT helpdesk support for employees and contractors, handling tickets, user administration, desktop troubleshooting, hardware and software provisioning, asset tracking, account audits, patching, VIP support, and special projects. Requires experience with Okta, Google Workspace, macOS, Windows, networking, VoIP, telephony, and PC hardware. The role is office-based and requires U.S. work authorization; visa sponsorship is unavailable.

Provides administrative and underwriting support for builders risk insurance, including reviewing submissions, maintaining underwriting data, preparing quotes and policy documents, communicating with agents and brokers, tracking deadlines and outstanding requirements, reviewing preliminary risk reports, supporting compliance and quality control, compiling reports, and maintaining organized records.

Manages and grows a portfolio of public company Directors and Officers liability accounts across the Central Region. Responsibilities include underwriting middle-market and large-cap organizations, assessing SEC filings and financial performance, evaluating governance and risk practices, monitoring litigation and regulatory trends, negotiating complex placements and renewals, leading client and broker discussions, and mentoring team members. Expertise in D&O, Employment Practices Liability, and Fiduciary Liability insurance is required.

Supports property underwriters by entering submissions, preparing renewals, obtaining risk reports, conducting catastrophe analysis, and processing policies and endorsements. The role also performs premium entry and reconciliation, maintains underwriting reports, follows up with brokers for audit information, and uses risk and insurance software systems. Strong organization, communication, multitasking, and advanced Microsoft Excel and Word skills are required.

Performs strategic technical business analysis for investment technology projects supporting ETF and indexed strategies. Analyzes requirements, business processes, and data-platform enhancements; designs solution recommendations; coordinates user testing and business sign-off; supports critical production applications; and manages risks, issues, stakeholders, and project communications. Builds relationships with internal partners and identifies opportunities to improve productivity through technology.

Owns day-to-day administration, configuration, maintenance, troubleshooting, and improvement of procurement technology platforms. Supports intake, approvals, contract routing, supplier workflows, data quality, reporting, documentation, and user adoption. Partners with procurement, technology, and business stakeholders to improve processes and user experience. Also supports workflow automation, intelligent routing, AI agents, and data-driven insights. Requires 3–5 years of procurement operations, systems support, business operations, or process improvement experience.

Lead and develop Flexport’s mid-market sales team in Chicago. Responsibilities include hiring, coaching, setting quotas, monitoring performance metrics, improving consultative sales processes, driving revenue growth, and executing go-to-market strategies. The role partners with senior leadership and offers a 50/50 base salary and uncapped bonus compensation model.

Coordinates onboarding for new and rehired employees, including communications, documentation, orientations, system access, surveys, and calendar management. Maintains accurate HRIS records and confidential personnel files, processes status and compensation changes, supports HR audits, E-Verify, and labor law compliance, and manages employee and manager support requests. Also coordinates uniforms and name badges and prepares promotion reports.

Lead post-sales operations for Professional Services, Customer Support, and Customer Success Engineering. Manage forecasting, utilization, margins, capacity, headcount, systems implementations, AI workflows, metrics, close activities, cross-functional handoffs, and customer experience improvements. Lead a small operations team while partnering with Finance, Sales, R&D, HR, and customer leadership to improve performance and operational execution.

Evaluates and underwrites workers’ compensation insurance policies, renewals, and modifications according to company guidelines and risk appetite. Develops risk assessment models, analyzes loss histories and inspections, ensures regulatory compliance, documents decisions, and advises agents, brokers, clients, and internal teams. Monitors market and regulatory trends, supports profitable growth and retention, and may coach underwriting staff. The role is primarily onsite in Gainesville, Georgia, with one remote workday weekly and occasional travel.

Manage a large inventory of complex workers' compensation claims, lead investigations to determine liability and compensability, negotiate settlements within authority, maintain detailed claim files, communicate with stakeholders, and potentially coach staff. Remote within Illinois.

Handles executive liability claim files, analyzing coverage and liability, issuing coverage opinions, managing defense counsel, developing litigation and settlement strategies, investigating claims, attending mediations or arbitrations, managing reserves and payments, and ensuring compliance with legal and company requirements. Provides claim-related guidance to underwriters, reinsurers, and internal teams.

Build and maintain reliable, scalable post-trade systems supporting global trading across asset classes. Coordinate solutions across varied inputs, outputs, and latency requirements using Python and C++ within distributed systems. Apply Linux performance tuning and networking expertise, work with relational databases, and integrate FIX capabilities including execution management, market data, and drop copy. Collaborate effectively, communicate clearly, and own projects in a fast-paced trading environment.

Own and manage BI solution products by translating customer needs into technical requirements, prioritizing development, coordinating stakeholders, promoting adoption, and ensuring successful delivery. The role involves analyzing business problems, creating actionable BI solutions, presenting to varied organizational levels, and potentially supporting BI development and data engineering. It may also indirectly lead analytics consultants and data engineers.

Leads and controls financial reporting and analysis while developing HCSC’s financial reporting strategy. Advises senior management on financial accounting, reporting, and analysis. The role supervises and develops employees, manages performance and hiring, coordinates projects across the organization, and presents financial information. It requires strong analytical, communication, organizational, and project management skills, with preferred experience in CPA certification and insurance statutory accounting and reporting.

Provides service to Service Benefit Plan subscribers, promotes enrollment growth among active and retired federal employees, and acts as a liaison between members, federal agencies, and HCSC. The role requires travel, including overnight stays, and uses a company-leased car. Responsibilities involve insurance account servicing, marketing, sales, and customer relationship management within an assigned territory.