Regional Director, Western Chicago Suburbs

Lucky Lincoln is the 5th largest Route Gaming Terminal Operator in Illinois, with $100M+ in annual revenue and a mission to become the largest. At Lucky Lincoln, we’re reimagining how operations, sales, and marketing work, from centralized departments to powerful regional business units.

THE ROLE

We are actively seeking a dynamic, results-oriented Regional Leader to join our team. As a Regional Director, you will run a large slice of the business (approx. $20 million annually) with full P&L ownership, leading a small, scrappy team across ops, sales, and marketing.

You’ll lead a small, scrappy team, including an Ops Lead (managing Techs, Warehouse, & Cash Collections), a Sales Lead, and a Marketing Lead, each working together to outperform the other districts in service, revenue, and customer satisfaction.

You’ll set clear priorities for your region, lead, manage & develop a team, solve problems, and track your progress using robust data. You’ll be part of a high-accountability, high-support team. Bonus structure is tied directly to your district’s financial performance and growth.

This role is for someone who wants to run a business within a business and grow with us.

WHAT YOU'LL DO

• Manage $20M+ district P&L, drive profitability and operational efficiency
• Lead Sales, Ops, and Marketing leads as a unified, high-performing team
• Ensure 1-hour service closeouts and zero cash discrepancies
• Oversee customer satisfaction, loyalty programs, and regional growth metrics
• Build relationships with location owners across the region to drive retention and build future pipelines
• Hire, coach, and evaluate frontline team members
• Lead your assigned district to compete and outperform other regions in revenue, margin, and growth

WHO YOU ARE

• You think like an entrepreneur and operate like an owner
• You have a proven ability to drive revenue growth and manage a P&L
• You thrive on healthy competition and have 5+ years of experience building winning teams in route-based, multi-unit, or field operations
• You don’t wait for direction; you take it, run with it, and ask for more
• You believe in accountability, clear expectations, and constant improvement
• You want a career path with serious upside, from frontline lead to future VP
• You’ve lived EOS, or you’re excited to learn it and run on it
• Experience managing cross-functional teams (ops, sales, marketing)
• Experience in route gaming, vending, logistics, or similar is helpful but not required