VP, Operations in Chicago, Illinois at Lucky Lincoln Gaming LLC

About Lucky Lincoln Gaming

Lucky Lincoln Gaming is the 5th largest route gaming operator in Illinois, generating over $110M in annual revenue, and we're building to become the largest. We're scaling fast, and the field is where our growth is won or lost. This is a company for people who want real ownership, real accountability, and the chance to build something bigger as we expand into new states and new markets.

About the Role

The VP of Operations will own how Lucky Lincoln runs in the field: Collections, Vault, Service and Equipment Uptime, Project Execution, and the Call Center that supports all of it. This is a pure operations seat. Sales and territory growth stay with the CEO and the Regional Directors; your job is to make sure the machines, the cash, and the crews behind them run right, every day, across every region.

This is not a desk job with a dashboard. You will spend the majority of your time in the field, in bars, restaurants, and truck stops, riding with collectors and technicians, inspecting locations, and validating that what the reports say is actually happening on the ground. If a standard is slipping, you find it before it shows up in the numbers. You will build the operating playbook, the standards, and the bench strength that let this function scale as Lucky Lincoln grows into new territories and new states.

Local to Chicago is required.

What You'll Own

• Statewide field operations: Collections, Vault and Cash Integrity, Service Response, and Equipment Eptime across all Illinois territories.
• Direct oversight of Collections, Vault, Projects, Call Center, and Field Service/Tech, plus the Central and Southern Operations Managers.
• Boots-on-the-ground validation: routine, unannounced visits to locations to inspect equipment, verify collection and service standards, and catch problems before they surface in the data.
• The operating playbook: Standards, SOPs, and quality benchmarks that keep execution consistent across every region and every crew.
• Bench strength across the operations org: identify, coach, and develop the next generation of operations leaders.
• Operational readiness for growth: build the systems and standards now that will hold up as the route expands within Illinois and into new states.
• Use performance and field data to spot trends, correct problems early, and raise the standard for how operations runs.

What Success Looks Like

• Every region operates to the same standard: cash integrity, service response, and equipment uptime hold consistent across territories.
• Field validation is routine, not exceptional. Location and equipment issues are caught by your team before they become customer or compliance problems.
• The operations org runs on documented standards, not institutional memory. New hires and new regions ramp against a playbook, not tribal knowledge.
• Leadership bench is strong enough to promote from within as the footprint grows.
• Operations is ready to stand up in a new state on short notice when the time comes.

What We're Looking For

• 10+ years in multi-unit, route-based, or service-heavy field operations, with direct ownership of collections, service, or cash-handling functions.
• Directly managed operations managers or supervisors; comfortable running a multi-layer field organization.
• Built or materially redesigned an operating playbook or SOP set, not just executed within one someone else built.
• A track record of spending real time in the field, not just reviewing reports about it. You catch what the dashboard misses.
• Hired, developed, and held accountable operations-level leaders.
• Comfortable with cash-intensive, regulated, or compliance-sensitive operations; route gaming background is a plus, not a requirement.
• Accountable and results-driven, with the judgment to know when a standard is slipping before it shows up in the numbers.
• A coach, not a micromanager, who builds leaders rather than doing their jobs for them.
• Motivated by building something bigger than yourself, with the appetite to help take this operation into new states.

Compensation

Base salary range of $180,000 to $220,000, plus a performance bonus with a 25% target, tied to statewide operational KPIs including collection cadence adherence, equipment uptime, service response time, and cash integrity.

Highland Holdings and its portfolio companies are equal opportunity employers. We evaluate all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.

We offer a full suite of benefits, including medical, dental, vision, 401(k) matching, and more.