Sales Manager Job

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