This is the mid-market seat at an AI-first loss-prevention platform that turns a retailer’s existing cameras into real-time theft, fraud and safety detection. It pays $80K–$120K base against $160K–$240K OTE on a true 50/50 split, based in New York, in the office four days a week, working directly with the founder and CEO. You cover US retailers with 5–30 locations. Pricing runs about $6,000 per location per year, so deals range from ~$30,000 to ~$180,000, with shorter cycles than enterprise and room to expand as each retailer opens doors. The seat rewards a fast, disciplined hunter who wants to learn a category up close from the person who built it.
Not the right location or comp? See the other roles I’m filling.
What is this role, exactly?
The product rides infrastructure every retailer already owns: their camera network. The platform layers AI detection — shoplifting, unscanned items, fraud, watchlists, safety — on top of installed cameras, or ships as an integrated platform for new deployments.
In mid-market, that matters even more. Retailers with 5–30 locations mostly have nothing like this today. You’re not displacing an incumbent. You’re bringing the first real loss-prevention technology to an owner or operator who feels theft on the P&L every month.
Why is this different from a normal mid-market sales job?
Greenfield, not rip-and-replace. Most of your buyers have no system to replace. The conversation is about the shrink they already know they have.
A buyer who feels the pain directly. In a 5–30 location retailer, the person you talk to often owns the P&L. Shorter path from first call to signature.
Learning next to the founder. Four days a week in the office with the CEO, who has closed the company’s deals to date. You see how the product gets sold, objection by objection, instead of guessing from a deck. That matters, because a founder can’t hand you a playbook he never wrote down — in this seat you watch it being written.
Land-and-expand still applies. Per-location pricing means a retailer that adds stores adds to your number.
How does this compare to the enterprise seat?
Same company, same product, a different buyer and a different working life. The enterprise seat demands deep loss-prevention domain and runs remote; this one trades that bar for speed, volume and a seat next to the founder. For the wider checklist, what good early-stage AE roles look like is the frame I use.
| This mid-market seat | The enterprise seat | |
|---|---|---|
| Buyer | US retailers with 5–30 locations | US retailers with 30+ locations |
| Deal size | ~$30,000 to ~$180,000 | ~$180,000 and up; a 150-location rollout is ~$900,000 |
| Competition | Mostly greenfield — no system to replace | Legacy camera-and-VMS vendors; the budget already exists |
| Cycle | Shorter — the buyer often owns the P&L | Enterprise cycles, pilot to chain-wide rollout |
| Base / OTE | $80K–$120K / $160K–$240K | $125K–$150K / $250K–$300K |
| Where you work | New York, four days a week with the founder | Remote US, New York preferred |
| Domain knowledge | A strong plus, not a requirement | Non-negotiable — buyers expect to learn from you |
If you’re benchmarking the number against other offers, what an early-stage Account Executive actually earns has the market ranges.
A weekly newsletter for founding AEs selling before the playbook exists.
Mostly the craft of the job; sometimes the career around it. Five minutes a week.
Where is the upside in this role?
Faster cycles mean more at-bats. A 10-location pilot that rolls out to 25 locations moves one account from ~$60,000 to ~$150,000. Strong mid-market sellers who learn the category and the buyer become the natural candidates as the company builds out its enterprise motion.
Who is this role actually for?
A hunter with 3–8 years of B2B closing who builds their own pipeline, moves fast, and wants to be in the room with the founder. Retail, physical security, or store-operations selling experience is a strong plus. You want New York, you want an office, and you want to learn a category from the inside.
Who it isn’t for: a seller who needs inbound to hit their number, or wants to be fully remote.
What would I push on before signing?
The first-year definition of success, how targets account for building pipeline from scratch, and what support you get as you ramp. This is a hunting seat at a seed-stage company: nobody hands you a book. Revenue is real, the motion is still being built, and you’ll want a clear picture of how earlier sellers have ramped. I’ll walk you through all of it honestly on a first call.
The questions worth asking before you sign covers the rest of what I’d bring to a first call.
The same company is hiring a Founding Enterprise Account Executive covering retailers with 30+ locations, remote US. See that role here.
