Vice President, Marketing in Chicago, Illinois at Lucky Lincoln Gaming LLC

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

You will own marketing for Lucky Lincoln Gaming end to end, from location-level field marketing and player engagement to the brand our location partners and future partners see. This is a builder's role. You set the annual marketing plan, then get it done in the field with a team of two, a Manager of Field Marketing and a Loyalty Program Marketing Manager, reporting to our Chief Operating Officer. Roughly 80% of the role centers on marketing Lucky Lincoln to location owners and driving two numbers: same-store sales growth inside our existing partner locations, and market share growth as we climb from 5th largest toward the top spot in Illinois.

That means driving player traffic and engagement inside our partner locations, running localized campaigns and events, helping partners grow their gaming business, equipping our revenue team to win new locations, and owning the go-to-market rollout of our revamped player loyalty program. The rest is brand work with real teeth: a full rebuild of our website, a refresh of our outbound marketing, and positioning the brand to reach younger audiences as we open the Chicago market. What you build here becomes the marketing playbook for everything that comes next.

What You'll Own

• The annual marketing plan and budget for Lucky Lincoln Gaming, built by you and executed hands-on with your team

• Location-level marketing programs, promotions, and player-facing events across our Illinois network, with regular time in the field alongside location owners and players

• The rollout and ongoing marketing of our revamped player loyalty program

• Partnership with sales and operations leadership on location acquisition and retention, equipping the revenue team with the brand, materials, and campaigns they need to win

• A complete rebuild of our website and a modernization of our outbound marketing, strengthening how the brand shows up to location owners, players, and younger audiences, particularly in Chicago

• The definition of marketing success: KPIs, measurement framework, and reporting cadence for spend efficiency and year-over-year same-store sales growth, operationalized with our finance and data teams

• A small marketing team and a limited set of outside vendors in a primarily in-house operation

• Fresh campaign ideas, turned into executed programs with clear results

What Success Looks Like

• Same-store sales grow year over year across our partner locations, driven by field campaigns, promotions, and loyalty programs you can point to

• Lucky Lincoln gains market share in Illinois, with marketing directly supporting new location acquisition and retention as we climb from 5th largest toward the top spot

• Marketing spend efficiency improves and is measured against a framework you built

• The revamped loyalty program launches on time and drives measurable player engagement in the field

• A rebuilt website and modernized outbound presence that win with location owners and younger audiences, including in the new Chicago market

What We're Looking For

• 10+ years of progressive marketing experience, including leadership of small teams

• A track record in multi-unit, decentralized consumer businesses; hospitality groups, restaurant or franchise organizations, multi-location consumer services, or small-format gaming translate especially well

• Proven ability to drive customers into physical locations through local marketing, events, promotions, and loyalty programs

• Experience supporting B2B growth, marketing to business owners or franchisees while engaging their end customers

• A doer: comfortable setting up an event on a Friday night, running a raffle, and talking with players and owners, then presenting results to executive leadership on Monday

• Sharp on measurement: you know what to measure, why it matters, and how to tie spend to outcomes

• An executive presence that earns buy-in from an ambitious, opinionated leadership team

• Able to be disclosed to the Illinois Gaming Board as a sales agent and to maintain eligibility under applicable Illinois gaming regulations

• Bachelor's degree required

Compensation

The base salary range for this role is $180,000 to $200,000, plus a performance bonus tied to marketing spend efficiency and same-store sales growth. Actual compensation within the range depends on experience and qualifications.

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.