Top Sales Jobs in Chicago, IL

Completes a nine-month sales training program focused on employee benefits, professional selling, and product knowledge. Supports sales offices through broker and customer meetings, cold calls, enrollment meetings, benefit fairs, post-sale service, and account executive assistance. Builds communication, presentation, negotiation, relationship-building, and analytical skills while learning MetLife’s group benefits products. Successful completion prepares the trainee to pursue an account executive role.

Supports the Group Benefits sales organization through training, customer meeting participation, technology exposure, and assigned sales duties. The intern will collaborate on a capstone project, present findings to leadership, develop business-to-business sales skills, and build professional networks. Successful completion may lead to an interview for a sales trainee position.

Sell pet insurance policies through inbound phone, email, and chat interactions. Build rapport with pet parents, educate customers on products, overcome objections, meet sales goals, and support retention through effective problem-solving. The role requires an active Property and Casualty license, completion of multistate licensing, reliable attendance, and availability for evening and rotating weekend shifts in a call center environment.

Manage a group benefits book of business ranging from 2 to 5,000 lives, serving as the primary broker contact and coordinating service delivery. Resolve escalations, support renewals, improve account performance, and identify cross-sell and growth opportunities. Lead client and broker meetings, provide consultative guidance on benefit plans, monitor service performance, and deliver data-driven engagement and education initiatives.

Manages strategic partnerships with benefits technology firms to drive sales growth, market expansion, partner enablement, data integration, and go-to-market initiatives. Owns partner relationships, develops joint business plans, coordinates cross-functional teams, manages pipeline development, and tracks performance metrics. Requires experience in group benefits or insurance distribution, benefits administration platforms, relationship management, and strategic stakeholder influence.