Waitwhile is seeking a Mid-Market Account Executive to expand its footprint across industries including retail, finance, government, education, and healthcare. This on-site role in Chicago, Illinois, United States, will own the full sales cycle—from prospecting and discovery through product demos, negotiation, and closing—with a focus on mid-market opportunities in the $30K–$150K ARR range. You will collaborate with BDRs, Marketing, Customer Success, and Sales Engineering to build pipeline, understand customer needs, and demonstrate Waitwhile’s value and ROI. This position is ideal for someone who enjoys owning the sales process, building strong customer relationships, and contributing to the growth of a fast-growing SaaS company. Responsibilities include pipeline generation through inbound and outbound efforts, running tailored demos, translating customer needs into business value, negotiating and closing deals, and working cross-functionally to improve targeting and the customer journey. You will use HubSpot to track opportunities and forecast, and contribute to data-driven pipeline reviews. Qualifications: 4–6+ years of B2B SaaS sales experience with a track record of closing Mid-Market or upper-SMB deals; strong consultative and value-based selling skills; excellent communication, presentation, negotiation, and storytelling abilities; experience navigating complex buying processes with multiple stakeholders; ability to work independently in a fast-moving environment; bachelor’s degree or equivalent. Bonus: experience selling into retail, education, or enterprise service

Waitwhile is seeking a Mid-Market Account Executive to expand its footprint across industries including retail, finance, government, education, and healthcare. This on-site role in Chicago, Illinois, United States, will own the full sales cycle—from prospecting and discovery through product demos, negotiation, and closing—with a focus on mid-market opportunities in the $30K–$150K ARR range. You will collaborate with BDRs, Marketing, Customer Success, and Sales Engineering to build pipeline, understand customer needs, and demonstrate Waitwhile’s value and ROI. This position is ideal for someone who enjoys owning the sales process, building strong customer relationships, and contributing to the growth of a fast-growing SaaS company. Responsibilities include pipeline generation through inbound and outbound efforts, running tailored demos, translating customer needs into business value, negotiating and closing deals, and working cross-functionally to improve targeting and the customer journey. You will use HubSpot to track opportunities and forecast, and contribute to data-driven pipeline reviews. Qualifications: 4–6+ years of B2B SaaS sales experience with a track record of closing Mid-Market or upper-SMB deals; strong consultative and value-based selling skills; excellent communication, presentation, negotiation, and storytelling abilities; experience navigating complex buying processes with multiple stakeholders; ability to work independently in a fast-moving environment; bachelor’s degree or equivalent. Bonus: experience selling into retail, education, or enterprise service