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
• Team sales overrides
• 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
• Team sales overrides
• 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