Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and develops Financial Representatives by coaching sales execution, overseeing onboarding and training, driving prospecting and production results, supporting recruiting and retention, and ensuring agency scorecard objectives are met. The role translates agency strategy into representative goals, monitors performance, promotes sales programs, maintains ethical standards, and reports production and recruiting activity to agency management. A valid driver’s license, automobile access, financial services sales experience, and required securities and insurance licenses are required.

Sell senior insurance solutions by assessing client needs, explaining policy options, completing applications, arranging payments, processing requests, and supporting claims. The trainee also follows up with clients, meets team KPIs, develops insurance expertise, and helps recruit and train insurance professionals in a competitive, inclusive environment.

Drive national advertising revenue by selling integrated radio, podcast, digital, and live-event solutions to brands and agencies. Develop strategic relationships with media holding companies, source new business, negotiate complex deals, meet revenue targets, and represent Audacy with senior agency and brand stakeholders. Collaborate cross-functionally on data-driven solutions, report revenue trends, lead business reviews, and support training and growth initiatives.

Develop new business and grow revenue by selling global freight forwarding, logistics, and warehousing services. The role prospecting, manages sales pipelines, negotiates and closes deals, builds strategic customer relationships, supports post-sale satisfaction, and collaborates with marketing, operations, and customer support. It also requires preparing sales reports, analyzing market conditions, meeting sales quotas, and traveling periodically up to 25%.

Leads IT Capability Request analysis for a federal enterprise IT program. Responsibilities include requirements elicitation, process and gap analysis, alternatives analysis, market research, ROMs, cost-benefit analysis, executive briefings, Agile backlog development, UAT leadership, change impact assessment, CX roadmap contributions, requirements governance, and mentoring business analysts. The role requires collaboration with government stakeholders while supporting ITSM development, governance boards, and approved capability implementation.

The Property Manager will oversee multiple Condominium Associations, ensuring customer satisfaction, managing budgets, analyzing financial reports, supervising projects, and maintaining property standards.

Build and maintain full-stack web applications and platform capabilities end to end. Design APIs, relational database schemas, and distributed systems with strong observability and monitoring. Partner with product stakeholders, participate in code and design reviews, mentor engineers, and raise engineering standards. The role requires onsite work in Chicago and involves developing telematics technology for trailer safety, cargo security, and transportation visibility.

Investigates complex insurance claims referred for potential fraud across auto, homeowners, and specialty lines. Reviews claim documents, medical records, property damage, online data, and investigative findings; conducts interviews, searches, site inspections, and surveillance as needed. Coordinates vendors, determines whether field investigation is warranted, validates evidence, documents outcomes, and recommends claim decisions, including denial or settlement. This is a remote desk-based role with no supervisory responsibilities.

Build relationships with business owners and decision-makers, research client needs, present tailored PEO solutions, and close sales. Manage the sales pipeline by tracking leads, opportunities, and activities in CRM tools; deliver proposals and work with internal teams to qualify prospects. Stay informed about PEO industry trends and competitors while helping small and mid-sized businesses with HR, payroll, benefits, and compliance solutions.

Own enterprise sales across named accounts, generating new revenue and closing complex deals with senior brand marketing and consumer insights leaders. Manage the full sales cycle from prospecting through negotiation and close, demonstrate AI-powered data solutions, build executive relationships, maintain accurate forecasts, and partner with Solutions Engineering, Product, and Marketing. The remote-first role requires up to 30% travel and targets enterprise contracts of $250K or more in annual contract value.