Cash & Route Collection Supervisor

Who We Are

Lucky Lincoln is the 5th largest Route Gaming Terminal Operator in Illinois, with $100M+ in annual revenue and a mission to become #1. As we scale to a regional district model, our collection teams are critical to protecting revenue, maintaining trust, and keeping operations running smoothly.

The Lead Route Collector plays an essential leadership role; setting standards, driving accountability, and raising the bar for one of the most important functions in the business.

Lead Route Collectors oversee the day‑to‑day performance of the route collection team, ensuring every collection, transfer, and record is executed with accuracy, security, and discipline. You’ll lead by example, coach collectors in the field, monitor compliance, and make sure every location is handled with professionalism and consistency. This is a hands‑on leadership role with real responsibility. You’ll report to the Operations Manager and work closely with the District Manager, gaining visibility into route operations, vault processes, and field standards.

For the right performer, this is a clear development path toward Operations Manager and future Operations Leader roles.

• Lead, train, and hold accountable a team of route collectors across assigned routes
• Ensure all cash collections, transfers, and reconciliations meet Lucky Lincoln’s accuracy and security standards
• Enforce SOPs, safety protocols, and compliance requirements across the team
• Conduct in‑field coaching to drive speed, precision, and professional conduct
• Maintain strong communication with the Ops Manager and vault team to resolve discrepancies within 72 hours
• Execute secure collections and system‑verified documentation using company tools
• Record accurate VGT meter readings and perform basic equipment checks
• Refill redemption terminals and ATMs as required
• Identify issues, report risks, and recommend improvements to route efficiency and safety
• Promote a culture of integrity, discipline, and continuous improvement

• A hands‑on leader who sets a high standard and keeps the team aligned
• Strong operational instincts with exceptional attention to detail
• Clear communicator who builds trust with teammates and location partners
• Mechanically curious with the ability to troubleshoot basic machine issues
• Calm, reliable, and professional in high‑pressure or safety‑sensitive situations
• Able to walk, lift, drive, and ride for extended periods

• High school diploma or GED
• Minimum age 21
• Clean driving record and valid driver’s license
• Ability to obtain and maintain:
  • Illinois Gaming Board Terminal Handler License
  • FOID card
  • PERC
  • Firearm Control Card (FCC)
• Ability to pass an extensive Illinois Gaming Board background check
• Firearm handling experience preferred

$26 - $28 per hour

Lucky Lincoln Gaming is an equal opportunity employer that values diversity and inclusion. Lucky Lincoln Gaming, Cloud9 Cannabis, Take Flight Hospitality, Midwest Real Estate, Aviator Coffee and Cocktails, and Pilot Pizza all provide equal employment opportunities to all employees and applicants for employment and prohibit discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available upon request for candidates taking part in all aspects of the selection process.