Top Sales Jobs in Chicago, IL

Early-career sales or onboarding role handling high-volume inbound calls, chats, and emails plus some outbound outreach. Advise small businesses on product selection, guide onboarding for successful adoption, use consultative selling, maintain Salesforce/CRM records, and meet performance goals.

The role involves developing insights and solutions to enhance productivity for sales teams, driving AI strategies, optimizing processes, and providing operational support while collaborating across teams.

Founding leader to build Gusto's PEO sales org 0->1 while acting as a player-coach. Design sales motion and Salesforce pipeline, hire and onboard sales talent, develop channel strategy, convert existing payroll customers, plan around PEO selling season, collaborate cross-functionally, use data and AI to drive decisions, and ensure team expertise in PEO compliance and employment regulations.

The Expansion Account Executive will drive revenue by engaging customers through outreach, managing consultative sales calls, and optimizing sales strategies using AI. Key duties include tracking opportunities in Salesforce, collaborating with teams, and meeting monthly ARR quotas.

Lead and develop a team of Expansion Account Managers to drive upsell, cross-sell, retention, and expansion revenue. Own pipeline management, forecasting, sales coaching, playbook optimization, CRM-driven segmentation, and analytics to improve engagement, productivity, and long-term customer value.