WIN Reality is changing how baseball and softball players across the world train to get better. Our team is full of world class developers changing the VR landscape, former professional ballplayers dedicated to improving the way the game is played, and people passionate about creating a one of a kind experience. We’re always looking for talented people to join our team, and to continue pushing the boundaries of what’s possible.

Head of Strategic Finance

WIN Reality | Reports to CEO

About the Role

WIN Reality is building the future of sports through innovative training products and a growing footprint of SmartPark locations. As we scale across units, channels, and capital structures, we need a Head of Strategic Finance who can give leadership real-time financial clarity — and keep giving it as the company evolves over the next decade.

What we need is a long-term thought partner to the CEO who builds the analytical and systems backbone of the company — and continuously evolves it as we grow from our current footprint of SmartParks to many times its size, across new products, new geographies, and new capital structures.

If you want to spend the next 5+ years compounding the quality of decisions a company makes, this role is for you.

What You'll Own Over Time

The Unit Economics Engine

You own how we understand the economics of every SmartPark, every product line, and every channel — today and as the model evolves. As we open new SmartParks, launch new offerings, and test new pricing, you keep the unit economics framework current so leadership always has a clear read on what's working, what's not, and where to lean in. Over time, this becomes the company's source of truth for investment decisions.

Vendor & Cost Intelligence

You build and continuously expand an AI-powered system that organizes every vendor relationship, contract term, renewal cycle, and spend pattern. As our vendor base grows from dozens to hundreds, this system scales with us — enabling proactive renegotiation, consolidation, and cost discipline as a permanent capability rather than a one-time cleanup.

Commercial Finance Partnership

You're the financial counterpart to marketing and sales leadership for the long haul. You build the integrated view of spend, volume, and margin — and as channels mature and new ones emerge, you evolve the framework so leadership always sees commercial performance with the same clarity. This becomes a durable rhythm, not a one-time integration.

Revenue Operations Management

You’re the lead with the data team to build and maintain real time revenue data intra month to understand pacing, marketing efficiency and KPI reporting.

Internal Financial Business Partner

You’re the business partner with the data, operations, inventory management, fulfillment and marketing teams to manage data flow with the accounting and FP&A teams.

Leadership & Board Communication

You own the financial narrative across board meetings, investor updates, and internal leadership communications on an ongoing basis. As the company matures, governance expectations grow, and the cadence of reporting deepens, you scale the communication infrastructure to match — without scaling headcount.

Capital Strategy & Investor Relations

You're our long-term partner on capital formation. You build and maintain the data room, financial model, and investor materials as living systems — ready for the next debt facility, equity round, or strategic transaction whenever the moment arrives. Over a 5+ year arc, this means partnering through multiple rounds, refinancings, continued acquisitions, and potentially a larger transaction.

The AI-Powered Finance Stack

You treat the finance function itself as a product that gets better every quarter. You continuously rebuild reporting, forecasting, and analytical workflows using the best available AI tooling — shortening the loop between question and answer, year after year.

Strategic Thought Partnership

Where you bring judgment and collaboration, this role extends beyond pure finance into broader strategic questions — M&A evaluation, new market entry, pricing strategy, capital allocation tradeoffs. You earn this scope by being a clear, unbiased presenter of information rather than an operator pulling levers.

What You Won't Own

To be transparent about scope: this role does not own HR, program management, or operational decision-making, and accounting stays with the existing team. We're intentionally keeping the role focused on analytics, systems, capital strategy, and decision support. Leverage comes through systems, not headcount, and that philosophy holds as the company scales.

Who You Are

You operate with maniacal urgency. The most important problem gets solved today, not next quarter. You compress timelines that others assume are fixed, and you treat every week of delay as a week of compounding cost. Speed is a feature of your work, not a tradeoff against it.

You do the work yourself. You're not a delegator who reviews other people's models — you build the model, write the SQL, prompt the agent, and ship the deck. You stay close enough to the work that you'd notice if a number was wrong, because you built the thing that produced it. You scale yourself through systems and AI, not through layers of people.

You are unreasonable about what's possible. When someone says "that'll take six weeks," you ask why it can't take six days. When someone says "no one has built that," you treat it as a starting point, not a stop sign. You reject the premise that finance functions have to be slow, manual, or reactive.

You identify and attack the most important problem every day. You don't get lost in inbox triage or low-leverage reporting. You ruthlessly prioritize the one or two questions that will most change the trajectory of the business, and you put your hours there. Everything else is automated, deferred, or killed.

You build for automation by default. If you've answered a question twice, you build a system to answer it forever. You distrust manual processes and recurring meetings as substitutes for real infrastructure. Every quarter, more of your work runs without you.

You delete before you add. You believe the best part is no part, the best process is no process. You aggressively remove reports, meetings, and steps that don't earn their keep, before adding new ones. Complexity is a tax you refuse to pay.

You hold an extreme bar for quality and truth. You don't ship numbers you can't defend, and you don't soften an uncomfortable answer to make it more palatable. You bring leadership the truth, fast, even when it's hard — and you're equally fast to flag your own mistakes.

You are founder-mode aligned. You think like an owner, not a steward. You care more about the company winning than about the size of your team, the title on your business card, or the political comfort of your seat. You'd rather be indispensable to one person making great decisions than impressive to a room full of people.

You work hard, in the actual sense. This is a high-output, high-ownership role at a company moving fast. The pace is not for everyone, and we'd rather be honest about that than recruit someone who'd be unhappy here.

Background & skills:

• 8–12 years blending investment banking, PE, or corporate development with operational FP&A, ideally at a multi-unit business (location-based entertainment, fitness, retail, restaurants, or similar)
• Genuinely AI-native: you've built workflows with LLMs and agents and can speak to specific automations you've shipped
• Disciplined communicator: you present data and scenarios clearly and let decision-makers decide. You don't advocate, lobby, or insert yourself into operational calls outside finance
• Fluent in modern finance stack: NetSuite, SQL, and AI tooling
• Capital markets fluency: you've supported debt and equity raises and know what a clean data room looks like
• Bonus: experience with location-based businesses, sports/entertainment, subscription businesses, or hardware companies

How We'll Know It's Working

Leadership has real-time clarity on unit economics, vendor spend, and commercial performance — without asking. The finance function is a competitive advantage, and capital partners trust our numbers and our process.