Top Sales Jobs in Chicago, IL

Manage, hire, onboard, coach, and develop a remote team of Hybrid Development Representatives to generate pipeline and transition talent into xDR/AE roles. Monitor productivity metrics, deliver results on activity and revenue, collaborate with cross-functional teams, and report outcomes to senior sales and marketing leadership.

Lead strategy and execution for enterprise and mid-market GTM across multi-unit restaurant brands. Drive C-suite engagements, modernize sales motions, scale AI-powered forecasting, partner with Product/Engineering, and represent Toast in industry forums to win large, complex contracts.

Lead and grow a team of 6-8 Territory Account Executives focused on Thai & Asian restaurants. Coach reps (in Thai) on discovery, demos, and closing; optimize market funnels; gather frontline feedback for leadership; partner cross-functionally to ensure delivery; recruit, motivate, and drive quota attainment across the West Coast territory. Field sales role requiring travel.

Founding Retail BDR for Toast90: build prospect lists and perform high-volume outreach (80+ activities/day) to convenience stores, grocery and bottle shops; qualify leads, schedule meetings for Account Executives, use Salesforce to track activity, partner on sales strategy, and position the Toast Retail solution against competitors.