Vice President, Field Revenue and Operations

Lucky Lincoln Gaming LLC•Springfield, IL

5d•Onsite

About The Position

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.

Requirements

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
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

Nice To Haves

Background in regulated industries or route gaming is a plus, not a requirement
Experienced working within a structured operating environment (EOS is a plus)

Responsibilities

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