Top Tech Jobs & Startup Jobs in Chicago, IL

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.

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.

Owns full-cycle recruiting for engineering and design roles across energy, industrial construction, and related markets. Partners with engineering leaders on hiring strategies, builds talent pipelines, maps markets, engages passive candidates, screens applicants, negotiates offers, and provides recruiting market intelligence. The role also tracks sourcing effectiveness, strengthens talent networks and employment branding, and supports recruiting initiatives across multiple U.S. locations in a hybrid environment with up to 25% travel.

Design, develop, and maintain scalable data solutions, pipelines, architectures, migrations, and processing workflows. Troubleshoot complex data issues, improve system reliability, collaborate with cross-functional teams, mentor colleagues, and evaluate emerging technologies to enhance data operations.

Leads end-to-end integrated marketing programs spanning strategy, content, communications, events, and audience experiences. Translates stakeholder objectives into program briefs, messaging, journeys, KPIs, and delivery plans. Manages cross-functional teams, budgets, timelines, production, onsite execution, post-event follow-up, and performance measurement. Partners with senior stakeholders and creative teams while applying AI-enabled tools and workflow automation to improve marketing efficiency.