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 efficiencyLead Sales, Ops, and Marketing leads as a unified, high-performing teamEnsure 1-hour service closeouts and zero cash discrepanciesOversee customer satisfaction, loyalty programs, and regional growth metricsBuild relationships with location owners across the region to drive retention and build future pipelinesHire, coach, and evaluate frontline team membersLead your assigned district to compete and outperform other regions in revenue, margin, and growthRequirements:WHO YOU ARE
You think like an entrepreneur and operate like an ownerYou have a proven ability to drive revenue growth and manage a P&LYou thrive on healthy competition and have 5+ years of experience building winning teams in route-based, multi-unit, or field operationsYou don’t wait for direction; you take it, run with it, and ask for moreYou believe in accountability, clear expectations, and constant improvementYou want a career path with serious upside, from frontline lead to future VPYou’ve lived EOS, or you’re excited to learn it and run on itExperience managing cross-functional teams (ops, sales, marketing)Experience in route gaming, vending, logistics, or similar is helpful but not required Read LessLucky 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
• Relationships with the leaders of our corporate accounts, ensuring seamless execution across their portfolio of locations
• 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
Requirements: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.
Read LessLucky Lincoln is the 5th largest Route Gaming Terminal Operator in Illinois, with $100M+ in annual revenue and a mission to become the largest. As we shift to a regional district model, Operations Managers are the frontline leaders who keep our routes running smoothly, reliably, and profitably. This is a hands-on role for someone who thrives on discipline, accountability, and fast-paced field work.
THE ROLE
As an Operations Manager, you will own the day-to-day operational performance of a defined route within a geographical district. You’ll lead a team of technicians, ensure equipment uptime, protect cash integrity, and maintain strong relationships with location owners. You’ll be the operator who ensures every site in your area runs smoothly, consistently, and up to Lucky Lincoln standards.
You’ll report to a District Manager and play a key role in service quality, revenue protection, and customer satisfaction.
KEY ACCOUNTABILITIES
Lead, train, and hold accountable a team of 4–10 technicians Maintain vault accuracy, cash integrity, and route-wide cash reconciliation Oversee schedules, route assignments, and technician efficiency Equipment performance and management: Repairs, Swaps/Transfers, Regulatory compliance Ensure rapid service response times and equipment reliability Uphold location-level operational standards across the region Build strong partnerships with location owners to support retention Track route KPIs and use data to drive performance improvements Support the District Manager with insights, problem-solving, and operational execution Requirements:WHO YOU ARE
5+ years in operations, field service, route management, or warehouse leadership Experienced in leading hourly teams with clear accountability Strong operational instincts — you know how to run a tight route Comfortable with cash handling and accuracy under pressure Mechanically curious and able to guide techs through troubleshooting Calm under pressure and decisive in the field Strong communicator who builds trust with both teams and partners Gaming or regulated industry experience is a plus Able to obtain IGB credentialsREQUIRED QUALIFICATIONS
High school diploma or GEDMinimum age 21Clean driving record and valid driver’s licenseAbility to obtain and maintain: Illinois Gaming Board Terminal Handler LicenseFOID cardPERCFirearm Control Card (FCC)Ability to pass an extensive Illinois Gaming Board background checkFirearm handling experience preferredWHY THIS ROLE MATTERS
Operations Managers are the frontline stewards of our revenue and reputation. You’ll be trusted with high-impact responsibilities, direct access to operations leadership, and a meaningful path to advance into broader operational roles as Lucky Lincoln continues to grow.
OUR COMMITMENT
Lucky Lincoln Gaming is an equal opportunity employer that values diversity and inclusion. We provide accommodations upon request throughout the hiring process to ensure an accessible and equitable experience for all candidates.
We Run on EOS
At Lucky Lincoln Gaming, we run on EOS (Entrepreneurial Operating System). EOS is a set of concepts and tools designed to prioritize our vision, align our teams, and streamline processes, ultimately driving growth and accountability throughout the organization.
Our Core Values
Get it done attitude! We take ownership of our tasks and challenges, actively seeking solutions and utilizing available resources. While we strive to resolve issues independently, we are also open to seeking guidance when necessary, bringing forward options and ideas to effectively collaborate. 5 Star Hospitality! Our customers are paramount, and we prioritize their needs with a sense of urgency and attentiveness, with the aim of exceeding their expectations. We extend this hospitality mindset to our employees and colleagues, recognizing that their satisfaction contributes to overall success. Positive Culture! We engage our customers and coworkers with respect, positivity, and open communication. We always have each other's backs and foster a culture of collaboration and teamwork. Self-propelled! We have a strong desire to learn and grow both personally and professionally. With a pilot mentality, we are self-motivated and believe we can get anywhere we want to go. Communicate Forward! Effective communication is fundamental to our success. We prioritize keeping everyone informed and aligned, sharing information through appropriate channels to ensure clarity and transparencyEqual Employment Opportunity
Lucky Lincoln Gaming, Cloud9 Cannabis, Take Flight Hospitality, Midwest Real Estate, Aviator Coffee and Cocktails, and Pilot Pizza all provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available upon request for candidates taking part in all aspects of the selection process.
Read LessLucky Lincoln Gaming is hiring a Gaming Service Technician to join the Operations Team to inspect, maintain, and repair our inventory of gaming units in McHenry, IL. The Gaming Service Technician will troubleshoot, fix, and repair video gambling terminals in their assigned territory. The successful candidate must be 21 years or older, be detail oriented, dependable, and able to pass a detailed background check with the Illinois Gaming Board and the Illinois Department of Professional Regulations.
The Gaming Service Technician position is well-suited for you if you possess:
Ability to complete tasks with minimal direction.Strong communication skills.Mechanically and technologically inclined.Strong moral character and work ethic.Ability to walk, sit, stand, and lift up to 75 lbs. at any time.Compensation
$20+ USD
We Run on EOS
At Lucky Lincoln Gaming, we run on EOS (Entrepreneurial Operating System). EOS is a set of concepts and tools designed to prioritize our vision, align our teams, and streamline processes, ultimately driving growth and accountability throughout the organization.
Our Core Values
Get it done attitude! We take ownership of our tasks and challenges, actively seeking solutions and utilizing available resources. While we strive to resolve issues independently, we are also open to seeking guidance when necessary, bringing forward options and ideas to effectively collaborate. 5 Star Hospitality! Our customers are paramount, and we prioritize their needs with a sense of urgency and attentiveness, with the aim of exceeding their expectations. We extend this hospitality mindset to our employees and colleagues, recognizing that their satisfaction contributes to overall success. Positive Culture! We engage our customers and coworkers with respect, positivity, and open communication. We always have each other's backs and foster a culture of collaboration and teamwork. Self-propelled! We have a strong desire to learn and grow both personally and professionally. With a pilot mentality, we are self-motivated and believe we can get anywhere we want to go. Communicate Forward! Effective communication is fundamental to our success. We prioritize keeping everyone informed and aligned, sharing information through appropriate channels to ensure clarity and transparencyEqual Employment Opportunity
Lucky Lincoln Gaming, Cloud9 Cannabis, Take Flight Hospitality, Midwest Real Estate, Aviator Coffee and Cocktails, and Pilot Pizza all provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available upon request for candidates taking part in all aspects of the selection process.
As a Gaming Service Technician, your responsibilities will include:
Install, maintain and repair Lucky Lincoln products (video game terminals and redemption terminals).Preventative maintenance and configuration of computer/security networks.Transporting of company assets and equipment to licensed establishments and LLG’s warehouse.Collect, fill and perform basic maintenance on redemption terminals.Various warehouse duties including shipping/receiving, inventory control, etc.Adhere to all company policies and documented procedures.Interact with establishment/venues along with patrons in a courteous and professional manner.On-Call Service.Provide technical support on-site or via phone or other communication methods.Adhere to all company policies and documented procedures.Qualified candidates will have:
High school diploma or GED required.At least 21 years of age.Be able to pass a background check and obtain a Terminal Handler’s license from the Illinois Gaming Board required.Ability to work Friday through Monday from 4pm-2am CST (average 40-42 hours a week including OT.)Valid driver’s license with a clean driving record.Lucky Lincoln Gaming is hiring a full-time Route Collector to function as part of the Operations Team to pick up, deliver, and record cash collected from our Video Gaming Terminals or VGTs. The Route Collector will collect and deliver cash to and from our partner locations and return the cash to our vault. The successful candidate must be 21 years or older, be detail oriented, and pass a detailed background check with the Illinois Gaming Board and the Illinois Department of Professional Regulations.
Our team is committed to driving organizational growth. We are privately owned, fast-paced, and fast-growing! This is an outstanding opportunity with the potential to grow and advance in the operations department!
Duties and Responsibilities
Must be comfortable securing, handling, and transporting large sums of currency.Accurate and detailed recordkeeping of funds transactions.Filling redemptions terminals with cash and removing cash on video gaming terminals.Accurately recording meter readings from VGTs (Video Gaming Terminals).Maintain constant awareness of surroundings and communication of unsafe or dangerous conditions related to LLG's equipment or operations to management.Security and confidentiality of proprietary data and information.Perform minor maintenance of VGT machines when necessary.Firearm handling experience preferredSuccessful Candidates Will Have
Ability to complete tasks with minimal direction.Strong communication skills.Mechanically and technologically inclined.Strong moral character and work ethic.Ability to drive or ride in a vehicle for several hours per shift.Ability to walk, sit, stand, and lift up to 75 pounds at any time.Compensation
$20 - $20 USD
We Run on EOS
At Lucky Lincoln Gaming, we run on EOS (Entrepreneurial Operating System). EOS is a set of concepts and tools designed to prioritize our vision, align our teams, and streamline processes, ultimately driving growth and accountability throughout the organization.
Our Core Values
Get it done attitude! We take ownership of our tasks and challenges, actively seeking solutions and utilizing available resources. While we strive to resolve issues independently, we are also open to seeking guidance when necessary, bringing forward options and ideas to effectively collaborate. 5 Star Hospitality! Our customers are paramount, and we prioritize their needs with a sense of urgency and attentiveness, with the aim of exceeding their expectations. We extend this hospitality mindset to our employees and colleagues, recognizing that their satisfaction contributes to overall success. Positive Culture! We engage our customers and coworkers with respect, positivity, and open communication. We always have each other's backs and foster a culture of collaboration and teamwork. Self-propelled! We have a strong desire to learn and grow both personally and professionally. With a pilot mentality, we are self-motivated and believe we can get anywhere we want to go. Communicate Forward! Effective communication is fundamental to our success. We prioritize keeping everyone informed and aligned, sharing information through appropriate channels to ensure clarity and transparencyEqual Employment Opportunity
Lucky Lincoln Gaming, Cloud9 Cannabis, Take Flight Hospitality, Midwest Real Estate, Aviator Coffee and Cocktails, and Pilot Pizza all provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available upon request for candidates taking part in all aspects of the selection process.
Qualifications
High school diploma or GED required.At least 21 years of age.Be able to pass a background check and obtain a Terminal Handler’s license from the Illinois Gaming Board required.Ability to obtain and/or maintain firearms owners’ identification (FOID) and Permanent Employee Registration Card (PERC).Valid driver’s license with a clean driving record.Lucky Lincoln Gaming is hiring a Gaming Service Technician to join the Operations Team to inspect, maintain, and repair our inventory of gaming units in McHenry, IL. The Gaming Service Technician will troubleshoot, fix, and repair video gambling terminals in their assigned territory. The successful candidate must be 21 years or older, be detail oriented, dependable, and able to pass a detailed background check with the Illinois Gaming Board and the Illinois Department of Professional Regulations.
The Gaming Service Technician position is well-suited for you if you possess:
Ability to complete tasks with minimal direction.Strong communication skills.Mechanically and technologically inclined.Strong moral character and work ethic.Ability to walk, sit, stand, and lift up to 75 lbs. at any time.Compensation
$20+ - USD
We Run on EOS
At Lucky Lincoln Gaming, we run on EOS (Entrepreneurial Operating System). EOS is a set of concepts and tools designed to prioritize our vision, align our teams, and streamline processes, ultimately driving growth and accountability throughout the organization.
Our Core Values
Get it done attitude! We take ownership of our tasks and challenges, actively seeking solutions and utilizing available resources. While we strive to resolve issues independently, we are also open to seeking guidance when necessary, bringing forward options and ideas to effectively collaborate. 5 Star Hospitality! Our customers are paramount, and we prioritize their needs with a sense of urgency and attentiveness, with the aim of exceeding their expectations. We extend this hospitality mindset to our employees and colleagues, recognizing that their satisfaction contributes to overall success. Positive Culture! We engage our customers and coworkers with respect, positivity, and open communication. We always have each other's backs and foster a culture of collaboration and teamwork. Self-propelled! We have a strong desire to learn and grow both personally and professionally. With a pilot mentality, we are self-motivated and believe we can get anywhere we want to go. Communicate Forward! Effective communication is fundamental to our success. We prioritize keeping everyone informed and aligned, sharing information through appropriate channels to ensure clarity and transparencyEqual Employment Opportunity
Lucky Lincoln Gaming, Cloud9 Cannabis, Take Flight Hospitality, Midwest Real Estate, Aviator Coffee and Cocktails, and Pilot Pizza all provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training. We are committed to an inclusive, equitable and accessible workplace. Accommodations are available upon request for candidates taking part in all aspects of the selection process.
As a Gaming Service Technician, your responsibilities will include:
Install, maintain and repair Lucky Lincoln products (video game terminals and redemption terminals).Preventative maintenance and configuration of computer/security networks.Transporting of company assets and equipment to licensed establishments and LLG’s warehouse.Collect, fill and perform basic maintenance on redemption terminals.Various warehouse duties including shipping/receiving, inventory control, etc.Adhere to all company policies and documented procedures.Interact with establishment/venues along with patrons in a courteous and professional manner.On-Call Service.Provide technical support on-site or via phone or other communication methods.Adhere to all company policies and documented procedures.Qualified candidates will have:
High school diploma or GED required.At least 21 years of age.Be able to pass a background check and obtain a Terminal Handler’s license from the Illinois Gaming Board required.Ability to work Saturday to Tuesday, 8am-6pm or Thursday to Sunday, 4pm-2am CST (average 40-42 hours a week including OT.)Valid driver’s license with a clean driving record.Lucky Lincoln Gaming isn’t your typical route gaming operator. We’re scaling fast across Illinois, and the field is where our growth is won or lost. The District Manager is a front-line owner of partner success, revenue retention, and in-location execution across a high-impact portfolio of gaming locations.
This is not a support role. It’s a field leadership seat with real responsibility, visibility, and upside.
In addition to a base salary and benefits package, this position is also eligible to participate in our incentive program with uncapped commission potential.
The Role
You’ll own a portfolio of 20+ gaming locations representing approximately $10MM in annual revenue. You’ll be the first call for location owners, responsible for partner satisfaction, account retention, and helping stores grow. You’ll bring our brand to life inside each location, execute marketing and promotional programs, drive new sales, and ensure every site performs to standard.
This role sits at the intersection of sales, marketing, account management, and field operations. You’ll be out in the field, responding to issues, supporting service needs, building trust, and driving results.
What You’ll Do
Own relationships with assigned locations and serve as the primary point of contact for our location ownersIncrease district revenue through new sales and local partnershipsDrive account retention, contract extensions, and support new sales by strengthening partner relationships and identifying growth opportunitiesSupport location owner store growth through promotions, layout recommendations, and player engagement strategiesExecute in-location marketing for installs, grand openings, promotions, and ongoing player engagementAct as first responder for service-related issues, including machine performance concerns, escalations, and urgent location needsPerform minor service repairs and basic troubleshooting on machines when needed to protect uptime and player experienceCoordinate with Operations and Service teams to resolve complex or escalated machine issues quicklyIdentify revenue and performance opportunities using dashboards, reports, and field observationRequirements:2–4 years in field marketing, account management, sales, or customer-facing rolesExperience owning a book of business with revenue accountabilityStrong relationship builder and hands-on problem solver who becomes a trusted partner to location ownersData-aware and comfortable using dashboards and CRM toolsFamiliar with Illinois gaming environments or eager to learn quicklyEnergized by field work and frequent local travelWhy Lucky Lincoln
Real ownership over a meaningful revenue portfolioDirect impact on partner growth, satisfaction, and retentionHigh-visibility role inside a fast-scaling route gaming platformAutonomy to run your territory like a businessOpportunity to grow into senior field, sales, or regional leadership rolesCompensation tied to performance and impact Read LessLicensing Manager
Location: Illinois (Office/Field)
Compensation: $80,000–$100,000 base salary, with flexibility for candidates bringing advanced regulatory, licensing, or legal operations expertise.
About Lucky Lincoln Gaming
Lucky Lincoln Gaming is one of the largest Video Gaming Terminal Operators in Illinois, operating hundreds of licensed locations across the state. Licensing is a strategic capability that directly enables our growth. Every application submitted, renewal completed, and regulatory milestone achieved supports our ability to expand and operate successfully.
The Opportunity
Key Responsibilities
Own the end-to-end lifecycle of state and municipal licensing, renewals, amendments, and regulatory filings across multiple jurisdictions.Manage Illinois Gaming Board applications, local and state renewals, DOJ registrations, liquor licensing, municipal licensing, and related regulatory documentation.Coordinate licensing activities across Operations, Accounting, Real Estate, Legal, Sales, and external agencies.Maintain comprehensive licensing calendars, renewal schedules, and audit-ready documentation.Track multiple concurrent licensing projects while proactively identifying risks, resolving bottlenecks, and ensuring deadlines are met.Develop, organize, and continuously improve standardized licensing documentation and workflows.Utilize document management systems and AI-enabled productivity tools to improve efficiency and consistency.Serve as the primary internal resource for licensing status, documentation, and milestone tracking.Escalate regulatory risks or interpretation questions to executive leadership when appropriate.Support future expansion into new jurisdictions by developing scalable licensing processes.Success in This Role
Maintain timely and accurate licensing submissions and renewals.Build scalable systems for tracking licensing activities across jurisdictions.Continuously improve documentation quality and workflow efficiency.Become a trusted cross-functional partner for licensing execution and strategy.Support the company's continued expansion into new markets.Requirements:Qualifications
3–5 years of experience managing licensing, permitting, regulatory applications, or comparable documentation within a highly regulated industry (gaming, cannabis, healthcare, financial services, utilities, or similar).Experience owning application processes from initial preparation through submission, approval, and renewal.Strong document management experience, including assembling, organizing, tracking, and updating complex regulatory packages.Demonstrated ability to operate with a high sense of urgency in a deadline-driven environment.Comfortable making judgment calls on priorities, escalating issues, and driving work forward with minimal direction.Flexible, coachable, and able to adapt quickly as business needs or regulations change.Experience coordinating multiple concurrent projects and cross-functional stakeholders.Strong written communication and organizational skills.Proficiency with Microsoft Office, Google Workspace, document management systems, and AI-enabled productivity tools.Ability to obtain required Illinois Gaming Board credentials.Notary Public certification (or willingness to obtain within 90 days).Why Join Lucky Lincoln Gaming
As Licensing Manager, you'll own a business-critical function with visibility across Operations, Real Estate, Accounting, and Executive Leadership. You'll have the opportunity to build scalable processes, leverage modern technology to improve efficiency, and help position the organization for continued expansion into new jurisdictions while growing your own career.
Read LessAbout This Role
Lucky Lincoln is the 5th largest route gaming operator in Illinois, with $110M+ in annual revenue and an ambition to become the largest. We are building the revenue and operational engine that will carry us into multi-state growth, and this VP role is the person who runs that engine.
The VP of Field Revenue and Operations owns both how Lucky Lincoln grows and how it executes in the field across their territory. You will lead a team of Regional Managers, each running a $20M+ P&L across ops, sales, and marketing. Your job is to make them excellent at their jobs, and to build the systems, playbooks, and bench strength that let the business scale without breaking.
You will report to the COO and work closely with the CEO, with direct visibility into the highest levels of the organization. This is a high-engagement role in a founder-led business where senior leadership is deeply involved in field performance.
This is a role for a builder. A scaler. A leader who sees the whole board and is not afraid to take responsibility for it.
What You’ll Do
• Own territory revenue targets alongside operational outcomes, with full accountability for both
• Lead and develop a team of Regional Managers, holding them accountable for performance across ops, sales, and marketing in their regions
• Monitor pipeline health across all regions and intervene when territory revenue trends are off track
• Serve as the senior commercial escalation point for larger deals and at-risk accounts in the territory
• Build and continuously improve the operating playbook that scales from four Illinois regions to a multi-state footprint
• Own territory field execution: collections, cash integrity, service response, equipment uptime, and quality standards
• Drive operational consistency and margin discipline across every team in the field
• Develop bench strength: identify, coach, and build the next generation of Regional Managers
• Use performance data to surface trends, correct problems early, and improve execution across the organization
• Prepare the revenue and operational model for expansion into new states as route gaming legalization accelerates
Requirements:What Success Looks Like
• Territory revenue targets are met or exceeded quarter over quarter
• Regional Managers are high performers who can run their business without daily intervention
• The field runs on consistent standards: service, cash, quality, across all regions
• Territory operating margin holds or improves as we add regions
• Leadership bench is strong enough to promote from within as we scale
• The business is operationally and commercially ready to enter new states when the time comes
Who We’re Looking For
What you’ve done:
• Directly managed other regional or district managers, second-line leadership minimum
• Owned both revenue and operational outcomes at a territory or multi-region level, not just one or the other
• Managed through a sales function, not just an ops function
• Served as a commercial escalation resource for field teams closing larger or more complex deals
• Owned a multi-region or statewide P&L ($50M+), not a single region
• Built or materially redesigned an operating playbook, not just executed within one
• Hired, developed, and exited regional-level leaders
• Led entry into a new market or geography
• 10+ years in multi-unit, route-based, or service-heavy field operations
• Background in regulated industries or route gaming is a plus, not a requirement
Who you are:
• Accountable and results-driven across both revenue and operations
• Comfortable with scale and complexity
• A coach, not a micromanager
• Motivated by building something bigger than yourself
• Comfortable operating in a high-accountability environment with frequent senior leadership engagement
• Experienced working within a structured operating environment (EOS is a plus)
• Able to pass an extensive background check by the Illinois Gaming Board
• Comfortable in a field-based role; must live in the Downstate, IL area
Why This Role Matters
This position plays a critical role in allowing Lucky Lincoln to scale without breaking. The right person will have significant influence, visibility, and the opportunity to grow alongside the business as we expand into new states and new markets.
Compensation includes a competitive executive base salary, a performance bonus tied directly to territory results, and a clear runway for expanded responsibility as the company grows. This is an ownership-level role, not a caretaker position.
Read LessAbout This Role
Lucky Lincoln is the 5th largest route gaming operator in Illinois, with $110M+ in annual revenue and an ambition to become the largest. We are building the revenue and operational engine that will carry us into multi-state growth, and this VP role is the person who runs that engine.
The VP of Field Revenue and Operations owns both how Lucky Lincoln grows and how it executes in the field across their territory. You will lead a team of Regional Managers, each running a $20M+ P&L across ops, sales, and marketing. Your job is to make them excellent at their jobs, and to build the systems, playbooks, and bench strength that let the business scale without breaking.
You will report to the COO and work closely with the CEO, with direct visibility into the highest levels of the organization. This is a high-engagement role in a founder-led business where senior leadership is deeply involved in field performance.
This is a role for a builder. A scaler. A leader who sees the whole board and is not afraid to take responsibility for it.
What You’ll Do
• Own territory revenue targets alongside operational outcomes, with full accountability for both
• Lead and develop a team of Regional Managers, holding them accountable for performance across ops, sales, and marketing in their regions
• Monitor pipeline health across all regions and intervene when territory revenue trends are off track
• Serve as the senior commercial escalation point for larger deals and at-risk accounts in the territory
• Build and continuously improve the operating playbook that scales from four Illinois regions to a multi-state footprint
• Own territory field execution: collections, cash integrity, service response, equipment uptime, and quality standards
• Drive operational consistency and margin discipline across every team in the field
• Develop bench strength: identify, coach, and build the next generation of Regional Managers
• Use performance data to surface trends, correct problems early, and improve execution across the organization
• Prepare the revenue and operational model for expansion into new states as route gaming legalization accelerates
Requirements:What Success Looks Like
• Territory revenue targets are met or exceeded quarter over quarter
• Regional Managers are high performers who can run their business without daily intervention
• The field runs on consistent standards: service, cash, quality, across all regions
• Territory operating margin holds or improves as we add regions
• Leadership bench is strong enough to promote from within as we scale
• The business is operationally and commercially ready to enter new states when the time comes
Who We’re Looking For
What you’ve done:
• Directly managed other regional or district managers, second-line leadership minimum
• Owned both revenue and operational outcomes at a territory or multi-region level, not just one or the other
• Managed through a sales function, not just an ops function
• Served as a commercial escalation resource for field teams closing larger or more complex deals
• Owned a multi-region or statewide P&L ($50M+), not a single region
• Built or materially redesigned an operating playbook, not just executed within one
• Hired, developed, and exited regional-level leaders
• Led entry into a new market or geography
• 10+ years in multi-unit, route-based, or service-heavy field operations
• Background in regulated industries or route gaming is a plus, not a requirement
Who you are:
• Accountable and results-driven across both revenue and operations
• Comfortable with scale and complexity
• A coach, not a micromanager
• Motivated by building something bigger than yourself
• Comfortable operating in a high-accountability environment with frequent senior leadership engagement
• Experienced working within a structured operating environment (EOS is a plus)
• Able to pass an extensive background check by the Illinois Gaming Board
• Comfortable in a field-based role; must live in the Greater Chicago area
Why This Role Matters
This position plays a critical role in allowing Lucky Lincoln to scale without breaking. The right person will have significant influence, visibility, and the opportunity to grow alongside the business as we expand into new states and new markets.
Compensation includes a competitive executive base salary, a performance bonus tied directly to territory results, and a clear runway for expanded responsibility as the company grows. This is an ownership-level role, not a caretaker position.
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