Regional Director, Western IL

Posted 6 Days Ago
Be an Early Applicant
Macomb, IL, USA
In-Office
100K-150K
Senior level
Cannabis • Gaming • Real Estate • Cryptocurrency • Web3
The Role
Own revenue growth across 50–60 locations in Western Illinois. Manage sales and marketing budgets, renew contracts, develop new location pipelines, grow same-store performance, maintain licensing and compliance, build municipal relationships, and lead two District Managers. The role requires accurate forecasting, contract negotiation, sales leadership, relationship development with independent operators, and accountability for regional revenue performance.
Summary Generated by Built In

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.

Skills Required

  • 5+ years growing revenue in a field-based, multi-location, or route-based business
  • Track record of building and developing a sales team, ideally including other managers
  • Experience owning a budget and defending spending decisions
  • Comfort with contract negotiation and renewal cycles
  • Experience working in a licensed or regulated industry
  • Credibility with municipalities, local officials, and regulators
  • Fluency with numbers, forecasting, and performance analysis
  • Relationship-building ability with independent owners and operators
  • Entrepreneurial, ownership-oriented mindset
  • Route gaming, vending, beverage distribution, or similar field sales experience
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The Company
HQ: Chicago, IL
70 Employees
Year Founded: 2013

What We Do

Are you interested in working for the 5th largest terminal operator in the state of Illinois? If so, check out the opportunities Lucky Lincoln Gaming offers! Founded in 2013, Lucky Lincoln Gaming, LLC is a licensed Video Gaming Terminal Operator in Illinois. We provide exceptional service to our clients and customers. Our expertise and experience have enabled us to become a successful company ranking in the top Terminal Operators in Illinois in terms of average profit per location for operators in excess of 100 locations. As Lucky Lincoln Gaming, LLC continues to grow, we will be building out the infrastructure for several other entities in different industries including, Lucky Bet sport wagering, Midwest Property Management, and the new Cannabis company, Cloud 9 dispensaries and Highland Flour cultivation centers. We’re disrupting the industry with innovation! We are pioneers and innovators of our industry. We have swag. We have pride. We own our responsibilities and wake up every morning ready to be better than we were the day before. This is an adventure that has no limits. Why not jump on board? We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available on request for candidates taking part in all aspects of the selection process.

Why Work With Us

People are the most important ingredient at Lucky Lincoln Gaming. Each team member makes an impact on our business and we share a genuine entrepreneurial spirit and relentless drive to always raise the bar. Together, we nurture a deep sense of community in our organization with a true passion and love for what we do.

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