Sales Manager (Field Sales – Hospitality & Nightlife Solutions)

Job Title: Sales Manager & Field Reps (Hospitality & Nightlife Solutions) Location: Chicago Area (Field-Based) Open Roles: 2 Sales Managers, 8 Field Sales Representatives 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 Sales Manager Responsibilities 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 Field Sales Representative Responsibilities Prospect and visit bars, restaurants, and nightlife venues in your territory Present and demonstrate the platform to decision-makers Generate leads through in-person outreach and relationship building Manage your sales pipeline and activity using HubSpot CRM Close new business and onboard accounts Maintain strong relationships to support retention and upselling Represent the brand with professionalism, energy, and consistency Requirements Sales Manager 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 Field Sales Representatives Minimum 3 years of field sales experience Minimum 1 year of POS sales experience Strong communication, presentation, and closing skills Self-motivated with the ability to work independently in the field Reliable transportation for local travel Compensation & Growth Sales Manager: Base + override commissions (1099 contract with path to full-time) Sales Reps: Base pay + uncapped commission (start part-time with path to full-time based on performance) High earning potential across all roles Clear advancement opportunities into leadership and full-time positions Startup environment with strong upside and career growth 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