Job Description

Job Description

A huge part of physical retail is still invisible to the internet. Independent liquor and convenience stores run on a patchwork of old registers. Marketplaces can't see what's on their shelves, so they sell things that aren't there. Brands can't see what's selling. As commerce becomes AI-driven, that gap gets bigger: an AI agent can only sell what it knows is on the shelf right now.

Nightcap is the integration for stores that can't integrate, and the AI-native system that runs them. One small device between a store's barcode scanner and its register turns any independent store into a chain-grade store online: a live catalog and real-time sell-through, with no new register and no change at the counter. Around it we run the store: registers and payments, delivery on DoorDash, Uber Eats and Grubhub, in-store TVs and local ads, and a back office owners run by messaging us on WhatsApp. A photo of an invoice updates their costs and prices. A photo of a shelf tag becomes an ad on their TVs.

Install once, and the same connection serves many: marketplaces, brands, distributors, and soon the AI agents that will shop the physical world for people. We intend to be where the ground truth comes from for the long tail of physical retail.

The market is enormous and nobody has won it. About 95,000 US convenience stores belong to owners with ten stores or fewer, and tens of thousands of independent liquor stores stand beside them. We already power 1,000+ stores, we work with DoorDash to bring the stores it can't integrate online, and we're growing fast. This is the hire that scales it.

The role

You'll be our first General Manager and the CEO's right hand. This is the CEO job for our core business: the P&L, the team, the partners and the numbers are yours. You and our CEO run in parallel and work side by side every day.

What you'll own

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• Revenue, retention and collections: subscriptions, delivery, payments and hardware
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• Every new store live fast, and every problem fixed fast
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• The team: onboarding and support, our offshore sales team, and our reseller (ISO) partners
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• Our marketplace partners day to day, including our DoorDash program
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• A weekly scorecard you set, review and hit
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• The few big calls each quarter on where money and time go
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• Turning every repeated task into a system, and every system into software and AI agents
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Who we're looking for

Exceptionally smart, ambitious and relentlessly resourceful. Former founders especially. You run through walls, figure things out, and take a problem from idea to done. Deep experience is a plus, not a requirement: we care most about how fast you learn and what you've already done.

Not a professional manager. Someone who is an executive and an individual contributor at once. You can see the big picture and you get in the weeds. You plan, you execute, you make things happen yourself, and being AI native gives you the leverage of a whole team. In an AI-first company, that's now possible, and it's the job.

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• AI native: you already use AI to do in an hour what used to take a team a week, and you think in agents and automations before headcount
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• A master executor: nothing falls through the cracks, and everyone knows where everything stands
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• Relentlessly organized and metrics driven: unit economics, churn, contribution margin, cash
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• You fix what's broken, not just tune what's there
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• You've led small, scrappy teams, including remote and offshore people
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• You can walk into a liquor store, talk to the owner and walk out with a yes
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• Helpful: payments, POS, delivery or merchant software; liquor, convenience or grocery retail; ISO channels
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How we hire

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• A call with our CEO
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• A paid work trial on a real problem from our business, with our real numbers
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• Conversations with people who've worked with you. We take references seriously.
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What you get

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• A seat beside the CEO, scaling an AI-native company in a market nobody has won
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• Real authority from day one, and scope that grows as fast as you do
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• Base salary, a bonus tied to contribution margin, and meaningful equity
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• Remote in the US, with time in stores and with partners
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To apply, answer each of these in a few lines:

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• Tell me about the chip on your shoulder
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• The most impressive thing you've built or achieved.
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• Something you've built or automated with AI that would have been unthinkable just 6 months ago.
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