Sales Manager (Hospitality & Nightlife Solutions)

Sales Manager (Hospitality & Nightlife Solutions) Job Title: Sales Manager (Hospitality & Nightlife Solutions) Location : Chicago Area (Field-Based) Job Type: (1099 Contract/Part-Time Base + Commission) Path to Full-Time Overview We are a startup mobile ordering platform built for bars, restaurants, and high-volume nightlife venues. Our solution eliminates wait times, increases order frequency, and helps venues drive higher revenue through a seamless customer experience. We are building our Chicago sales team and are hiring a Sales Manager and 4 Field Sales Representatives to drive growth, build relationships, and establish a strong presence in the hospitality and nightlife industry. This is a ground-floor opportunity to join a performance-driven team with significant upside. What You’ll Do Recruit, train, and lead a team of 10+ field sales representatives Lead from the front with active prospecting, sales, and account acquisition Develop and execute strategic sales plans targeting bars, clubs, restaurants, and hospitality venues Oversee the full sales cycle from lead generation through closing Conduct warm outreach and build strong client relationships Lead negotiations and secure new business partnerships Utilize HubSpot CRM to manage pipeline, track activity, and forecast performance Analyze market trends and optimize sales strategies Collaborate with marketing to drive awareness and lead generation Coach team members on closing, objection handling, and performance improvement Ensure team accountability and achievement of sales goals Requirements Minimum 3 years of field sales management/supervisory experience Proven experience leading teams of 10 or more sales reps Minimum 2 years of POS sales experience Strong background in B2B sales, preferably in technology or hospitality solutions Experience managing full sales cycles and closing deals Leadership mindset with strong coaching and performance management skills Comfortable operating in a startup environment Compensation & Growth Base + override commissions (1099 contract with path to full-time) High earning potential across all roles Clear advancement opportunities into leadership and full-time positions Startup environment with strong upside and career growth 7-Day Paid Audition Period All shortlisted candidates will participate in a 7-day paid audition period with commission-based earnings. Successful candidates may be offered a long-term position upon completion of the audition. First 3 Months (Ramp Period) Base salary: $3,000–$4,500 per month ($36,000–$54,000 annually) Commission on personal sales Additional bonuses for strong early team performance After Ramp Period Base salary: $5,000–$7,500 per month ($60,000–$90,000 annually) Commission on personal sales Bonuses for achieving team targets Earning Potential Earnings are uncapped. The more you and your team sell, the more you earn. Additional Info Sales candidates should be prepared to demonstrate their sales ability as part of the interview process (compensated opportunity with earning potential) Experience Field sales: 2 years (Required) CRM software: 1 year (Required) Work Location On the road #J-18808-Ljbffr Naperville Area Chamber of Commerce