Fractional VP of Sales for point of sale and store technology companies
If the register goes down, the store stops. Buyers never forget that.
Point of sale, payments, self-checkout, electronic shelf labels, store analytics, loss prevention, workforce tools — anything that lives in the store sells against one fear. If it breaks, the store cannot transact. I was Client Director for Kroger at Toshiba Global Commerce Solutions, badged inside the retailer’s own technology headquarters and responsible for a book of $100M+ in annual bookings on point of sale and self-checkout. I know what a store-technology buyer worries about at 6 a.m. on a Saturday. This page is how that sale works, and what I do inside it as a fractional VP of Sales.
Based in Scottsdale, Arizona. I work in person across Greater Phoenix and remotely with founders across the US.
Store technology is bought by IT and judged by the stores.
The store-technology sale has two buyers with opposite instincts. IT and the CIO’s office want stability and fewer vendors. Store operations wants anything that saves a minute at the front end. You need both, and the field has a veto neither of them will admit to.
- The CIO and store systems. Uptime, support model, how you fit next to the POS, the network and the device estate.
- Store operations. Labor, lines, shrink, associate experience. They decide whether the pilot results are believed.
- Loss prevention and asset protection. Anything near the front end or the exit is their business, whether you invited them or not.
- Finance and procurement. Hardware refresh cycles, capital versus operating budget, the cost of a truck roll per store.
- The field. District and store managers. If your product adds a step to a busy shift, they will quietly make the pilot fail.
Most founders sell either IT or operations. The deals that roll out are sold to both, with the field brought in early.
Ten stores is a test. Two thousand is the sale.
Store technology lives or dies in the rollout plan. A pilot that works in ten hand-picked stores tells the retailer very little about the other two thousand.
What has to be settled before store one
- The rollout budget owner and the fiscal year it lands in — usually not the pilot sponsor.
- The success measure, measured the way the retailer already measures it, agreed in writing.
- The install, training and support model per store, with a real cost per store.
- How the product behaves when the network, the POS or the device fails. The answer has to be boring.
- The calendar: nothing new goes into stores from early fall through the holidays.
I worked inside a retailer through self-checkout expansion and a curbside program rolled out across thousands of stores. The vendors who scaled had answered the rollout question before the pilot started.
You are not competing with their features. You are competing with their relationship.
Every store-technology account already has a POS vendor, a payments provider and a services partner with years in the building. They get the first call when anything new comes up, and they will tell the retailer your product is a risk.
- Partner where you can. Many store-technology wins come through the POS vendor or the integrator, not around them.
- Find the sponsor who wants change. A new VP of stores or a CIO with a modernization mandate is worth more than a dozen happy store managers.
- Make the risk smaller than the incumbent says. A phased plan, a fallback, a support commitment and a reference from a retailer they respect.
I sat on the incumbent’s side of that table at one of America’s largest retailers. I know exactly what the incumbent says about you, and how to answer it.
From the vendor’s side and the retailer’s side.
At Toshiba Global Commerce Solutions I was Client Director for Kroger — Toshiba’s largest retail account globally — embedded on site at Kroger’s own technology headquarters, meeting weekly with the CIO’s office, and running a book of $100M+ in annual bookings on point of sale and self-checkout.
Before that I sold eCommerce and order management into the same retailers at IBM, Adobe, Demandware and ATG, and more recently sold computer-vision store analytics as VP of Sales for an AI company. The store is where all of it meets.
Retailers and brands I’ve sold into
Fractional VP of Sales for store-technology founders.
I help you run the sales motion and bring you in only where the founder is the difference. For a POS or in-store technology company that usually means:
- An ICP by format, store count, current POS and refresh timing, and a buyer map that includes the field.
- A pilot-to-rollout plan with the budget owner, success measure, per-store cost and decision date agreed before store one.
- A partner strategy with the POS vendors, payments providers and integrators already in your target accounts.
- The security, PCI and support-model answers built before IT asks.
- An NRF and trade-show plan that books the meetings before the show, not at the booth.
- A forecast that reflects rollout reality, so the board isn’t surprised by a twelve-month gap between pilot and revenue.
Store technology, answered.
Our pilot results are good but the rollout keeps slipping. Why?
Usually nobody owns the rollout budget, or it landed in a fiscal year you didn’t plan for. The pilot sponsor is rarely the person who funds two thousand stores. Find that person, put the per-store cost and decision date in front of them, and plan around the holiday freeze.
Should we partner with the POS vendor or compete with them?
Partner wherever you can. The POS vendor and the integrators are already trusted inside the account. If your product makes their installed base more valuable, they can carry you in. If it replaces them, plan for a long fight and a very senior sponsor.
Do you work with payments and fintech companies selling to retailers?
Yes, when the buyer is a retailer, a restaurant group or a brand with stores. The front-end decision involves the same people: IT, operations, finance, loss prevention and the incumbent processor.
How do you approach NRF for a store-technology company?
As a campaign, not a booth. The meetings are booked weeks before January, the staff know who they are there to meet, and the follow-up is planned before the show opens. I have worked 20+ NRF shows from small startup booths to the largest vendors on the floor.
Are you a full-time hire in disguise?
No. I am a fractional VP of Sales: senior, part-time, inside your deals for as long as the work needs it, then handed over, handed back or kept running as advisory. Services explains the shapes.
Notes from inside these deals.
Why enterprise deals stall after the demo
If a deal dies after the demo, it is rarely because the demo was bad. It is because you never mapped who can actually say yes.
When the founder should show up — and what the fractional VP is doing
Founder and fractional VP of Sales as partners in a complex enterprise deal: three stages that need the founder, three that only feel like they do.
Getting out of founder-led sales without losing the deals
Transitioning away from founder-led sales fails when the founder hands deals to a VP before a motion exists. Here is the sequence that keeps the deals, a 90-day plan, and how to hand off a live deal.
Other industries I work in: Retail technology · AI & computer vision · B2B companies in any industry · B2B SaaS · eCommerce & order management · Supply chain & logistics technology
Thirty minutes. Bring the store pilot that won’t become a rollout.
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