Top Sales Jobs in Chicago, IL

Own the technical side of international upmarket deals, including tailored demos, labs, solution architecture, integrations, security reviews, RFPs, business requirements, and go-live handoffs. Partner with sales, product, engineering, and implementation teams to demonstrate business value, manage technical risks, shape product improvements, establish repeatable solutions processes, and help build the international solutions organization.

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.

Conducts high-volume outbound and inbound outreach to prospective businesses, qualifies their needs, and schedules meetings for Account Executives. The role requires at least 100 daily outreach activities, effective communication across calls, email, and social channels, and strong organization, resilience, accountability, and customer empathy. High performers receive structured development toward an All-Bound Sales Development role and eventually a full-cycle Account Executive position.

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 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.