Top Sales Jobs in Chicago, IL

Supports sales teams by presenting Toast’s retail POS platform, identifying prospect needs, recommending solutions, troubleshooting issues, and communicating product gaps. Partners with Product Management, Marketing, and Sales Enablement to improve product positioning and training. Manages multiple customer implementations, attends industry events, and helps build processes for Toast’s emerging retail business.

Leads and coaches a multilingual team of 6–10 Business Development Representatives generating qualified restaurant sales pipeline. Responsibilities include hiring, onboarding, coaching, pipeline inspection, forecasting, call reviews, performance development, and partnering with Account Executives, Marketing, and Enablement. The role also supports strategic market expansion across Asian cuisine communities, adapts messaging, improves funnel efficiency, and directly coaches Mandarin-speaking representatives and prospects.

Generates qualified pipeline for enterprise account executives through outbound prospecting, cold calling, account mapping, lead nurturing, and scheduling discovery calls and demos. Maintains Salesforce records, collaborates with account executives and cross-functional teams, promotes new products, and supports enterprise marketing efforts. The role requires persistence, customer empathy, strong communication, organization, and comfort engaging senior decision-makers across large restaurant organizations.

Lead and coach a team of 6–8 Strategic Cuisines Account Executives across the West Coast. Drive sales productivity, pipeline performance, discovery, demos, and customized restaurant technology solutions in Thai. Partner with leadership to assess market opportunities, improve sales funnels, and coordinate delivery expectations across teams. This field-based role requires travel and local West Coast residence or relocation.

Source and close complex, multi-location retail technology deals across grocery, liquor, and convenience operators. Build pipeline, conduct executive discovery, demonstrate platform value, structure and negotiate deals, manage lengthy buying cycles, and ensure implementation handoffs. The role also develops repeatable sales processes, partners cross-functionally on product and commercial gaps, maintains Salesforce pipeline discipline, and represents retailer needs in product decisions.

Source and close complex, multi-location retail technology deals across grocery, liquor, and convenience operators. Build pipeline, conduct executive discovery, deliver value-based demonstrations, structure and negotiate deals, manage multi-stakeholder sales cycles, and own contracts through close. Partner cross-functionally on implementations, product feedback, and repeatable sales processes while maintaining Salesforce discipline, forecasting accuracy, and long-term revenue quality. This remote role requires 30% or more travel.

Source and close complex, multi-location grocery, liquor, and convenience retail deals. Build pipeline, conduct executive discovery, deliver value-based demonstrations and business cases, negotiate contracts, and manage full-cycle sales. Navigate buying committees, RFPs, compliance, and lengthy sales cycles while partnering with internal teams on implementation, product feedback, and deal structure. Establish repeatable upmarket sales processes, maintain Salesforce discipline, and optimize long-term revenue.

Lead and build Toast Retail’s Mid-Market sales function from the ground up. Manage and coach Account Executives while personally closing complex grocery, liquor, and convenience retail deals. Develop repeatable sales processes, qualification frameworks, business cases, proposals, forecasting practices, and competitive positioning. Partner cross-functionally with Product, Marketing, Enablement, Finance, Deal Desk, and Onboarding to support enterprise implementations and product improvements. Hire and develop a high-performing team, establish benchmarks, and transition from a player-coach role to full team leadership.

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.

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.