About 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

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.