Regional Director, Western IL

Lucky Lincoln Gaming LLC; Macomb (IL); On-site; USD 110,000 - 180,000; Full time

Benefits offered by this job

Medical, dental, vision

401(k) matching

Career growth opportunities

Job summary

Lucky Lincoln Gaming LLC is seeking a Regional Director to own revenue growth across a book of 50 to 60 locations in Illinois. You will manage contracts, licensing, and marketing spend, with accountability for ROI and same-store performance.

You will lead 1–2 District Managers, cultivate relationships with municipalities and regulators, and report directly to the CEO as the face of the region.

Qualifications

• 5+ years revenue growth in field-based, multi-location or route-based business.
• Proven track record building and developing a sales team, ideally including other managers.
• Experience owning a budget and defending how you spent it.
• Comfort with contract negotiation and renewal cycles.
• Experience working in a licensed or regulated industry, and keeping licensing/current.
• Credibility with municipalities, local officials, and regulators.
• Fluency with numbers: forecast, understand movements, explain without a deck.
• Strong relationship-building with independent owners/operators.
• Entrepreneurial mindset and owner/operator discipline.
• Route gaming, vending, beverage distribution, or similar field sales experience is a plus.

Responsibilities

• Own revenue growth across a book of 50 to 60 locations.
• Manage long-term revenue security through contract extensions and renewals.
• Oversee a sales and marketing budget and measure ROI.
• Drive same-store revenue growth through local marketing investments.
• Lead 1-2 District Managers with accountability for their teams.
• Build owner/operator relationships across the region and protect deals from competitive calls.
• Develop new location pipeline and closes within the territory.
• Manage licensing across the region: applications, renewals, and compliance.

Skills

Revenue growth

Sales team leadership

Budget management

Contract negotiation

Regulated industry experience

Municipal/regulator credibility

Forecasting/numbers

Relationship building with owners

Entrepreneurial mindset

Job description

Description

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 Regional Director owns a book of 50 to 60 locations and is measured on one thing: growth. You own the revenue in your region, the contracts that protect it, and the marketing dollars that grow it. You carry a sales budget and a marketing budget, and you decide where that spend goes and what it has to return.

This is a revenue seat, not an operations seat. Service, warehouse, and collections are handled elsewhere. Your job is to grow revenue, extend contracts long before anyone else gets a look at them, and put marketing spend into the locations where it moves same store performance. You are also the company's face with municipalities across your region, and you keep licensing clean so growth never stalls on paperwork. You lead 1-2 District Managers who carry account management and new sales. Their numbers are your numbers. You report directly to the CEO.

WHAT YOU'LL OWN

• Revenue growth across a book of 50 to 60 locations
• Long term revenue security through contract extensions and renewals, signed ahead of expiration, not at it
• A sales budget and a marketing budget, including where every marketing dollar goes and what it returns
• Same store revenue growth through targeted, location level marketing investment
• Two District Managers: hiring, coaching, performance, and quota accountability
• Owner and operator relationships across your region, deep enough that competitors never get a first call
• New location pipeline and closes within your territory
• Licensing across your region: applications, renewals, and compliance for your locations, kept current and never a reason a location goes dark
• Relationships with municipalities, local officials, and regulators in your markets, built before you need them
• Accurate forecasting and clear, honest reporting on your book

Requirements

WHAT SUCCESS LOOKS LIKE

• Your region grows revenue year over year and outperforms the portfolio average
• Contract extensions are signed early, and retention risk is flagged months out, not at renewal
• Marketing spend is allocated on evidence, and you can show the same store lift it produced
• Both District Managers hit their numbers, and at least one is ready for more
• Location owners in your region call you first when something changes
• Licensing is current across the book, with no lapses, no surprises, and no revenue lost to a paperwork delay
• You are a known, trusted name in your municipalities, and local decisions do not blindside us

WHAT WE'RE LOOKING FOR

• 5+ years growing revenue in a field-based, multi-location, or route-based business
• A track record of building and developing a sales team, ideally including other managers
• Experience owning a budget and defending how you spent it
• Comfort with contract negotiation and renewal cycles
• Experience working in a licensed or regulated industry, and the patience to keep licensing and compliance current
• Credibility with municipalities, local officials, and regulators, and the judgment to represent the company well in a room like that
• Fluency with numbers: you build the forecast, you know why it moved, and you can explain it without a deck
• Real relationship-building ability with independent owners and operators
• You think like an entrepreneur and operate like an owner
• You take direction, run with it, and come back for more
• You want a path with serious upside, and you intend to earn it
• Route gaming, vending, beverage distribution, or similar field sales experience is helpful, not required

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

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.