Top Entry Level Sales Jobs in Chicago, IL

Participants in the STAR Program gain hands-on sales training, develop relationship-building skills, obtain a state insurance license, and are positioned for career growth in sales roles.

The Sales Development Representative connects government leaders with OpenGov's technology, focusing on pipeline building, prospecting, and collaboration with Account Executives to secure demos and convert leads.

Serve as primary customer contact at a branch to quote, sell, and fulfill equipment rentals and supplies. Generate leads, manage accounts and reservations, dispatch deliveries, handle walk-in and call-in customers, negotiate pricing within policy, and maintain showroom presentation while providing excellent customer service.

Remote commission-based insurance sales role handling warm leads. Conduct virtual appointments, advise individuals and families on coverage options, and close solution-based sales. Flexible scheduling with training and mentorship; full- or part-time.

Perform outside route sales to grow product placement and inventory at off-premise accounts. Manage customer relationships, upsell cooler space and displays, meet monthly sales and merchandising goals, ensure equipment upkeep, monitor competitor activity, and maintain Red Bull brand standards while collaborating with district and peer teams.

Make outbound B2B calls to business leaders, qualify prospects, book high-value sales appointments, and meet weekly/monthly targets. Work full-time in an office-based environment with training, coaching, and clear progression toward higher earnings and commission-based pay.

1099 independent field sales role selling CPG products to independent retailers in Chicago. Visit stores, cold-pitch decision-makers, place orders via a mobile app, build relationships, and drive repeat high-volume sales. Weekly commissions and performance bonuses.

Support direct sales and distributor partners in an assigned territory by executing sales activities, delivering presentations and technical demonstrations, conducting needs assessments and sample cutting, providing ROI analysis, fostering distributor/customer relationships, and traveling to customer sites to support pre-sales and application needs.

Sell short-term luggage storage systems to businesses: prospect and speak with owners/decision-makers, educate on solutions, help select services, close deals, and manage a book of business. Full-time W-2 role with base pay, uncapped commission, and paid training.

The Sales Development Representative supports the Sales Team by managing customer inquiries, tracking projects, maintaining Salesforce records, and conducting research. They assist with lead conversion, follow up on quotes, and ensure customer satisfaction post-delivery.

The Sales Representative engages customers to promote products, generates sales, and manages relationships, cold calls, and reporting sales activities.

As a Sales Representative, you will engage consumers, promote energy services, foster relationships, meet sales goals, and provide excellent customer service.

As an Entry-Level Sales Representative, you will build a portfolio of accounts through research and prospecting, focusing on consultative sales in logistics.

Provide exceptional customer service and relationship-building while leveraging product knowledge to guide luxury jewelry purchases. Manage the sales process, maintain organization and professionalism, and follow up post-sale to ensure customer satisfaction.

Field sales role closing face-to-face sales within assigned territories. Train and educate store personnel, build relationships with in-store staff and vendors, expand brand presence via merchandising and new business development, gather competitive intelligence, complete call reports and administrative tasks, and resolve store-level issues.

Engage customers to assess vehicle needs, present Toyota product features and financing, guide test drives and sales closings, follow up for satisfaction, use CRM to manage pipeline, collaborate with finance and service, meet monthly sales targets, and participate in ongoing product and sales training. Requires a valid driver’s license.

Engage customers, guide them through vehicle selection and purchase, deliver white-glove digital deal handoffs, conduct test drives, and build pipeline via equity mining, service-lane engagement, and follow-up. Use CRM (VinSolutions, Tekion) and AI tools, meet monthly sales targets, protect CSI, and work evenings/weekends as needed.

Entry-level outbound sales role focused on outbound pipeline generation for commercial real estate. Research and qualify target owners and brokers, use HubSpot and LinkedIn Sales Navigator to build/manage pipeline, execute full sales cycle alongside senior reps, develop repeatable prospecting systems and AI workflows, and rapidly progress to carrying quota and sales leadership responsibilities.

Entry-level sales role focused on prospecting and developing customer relationships for truckload, temperature-controlled freight across the U.S. and Canada. Support shipment execution, hit activity KPIs, use company tools, and follow structured sales training while building a pipeline through phone, email, and LinkedIn.

Sell ADT security and smart business solutions to small business customers by building trust, customizing systems, generating leads in a territory, conducting post-installation follow-ups, and maintaining long-term relationships. Role requires in-person customer visits, consultative selling, and use of technology to manage sales activities.

Sell ADT security and smart business solutions to small business customers through in-person visits. Assess needs, customize system recommendations, generate leads within a territory, close sales, and perform post-installation follow-ups to build long-term customer relationships and referrals.

Re-engage former ADT customers to sell updated security, automation, and life-safety solutions. Deliver tailored presentations and proposals, follow up after installation, generate referrals, and identify new leads within a designated territory.

Sell ADT security and smart business solutions to small business customers by consulting on needs, customizing system proposals, conducting on-site visits, following up after installation, and generating new leads within a territory. Build trust with decision-makers, recommend integrated security, automation, and life-safety options, and maintain long-term customer relationships to drive referrals and revenue.

Re-engage former ADT customers to sell security, automation, and life-safety solutions; deliver sales presentations and proposals; perform post-install follow-ups; generate new leads; use tech to manage pipeline; travel within a territory using your own vehicle.

Sell ADT security and smart business solutions to small business customers by assessing needs, customizing system recommendations, generating leads in a territory, conducting on-site visits, and performing post-installation follow-ups to build long-term relationships.