You sell software to retailers. That sale has its own rules.
eCommerce, order management, point of sale, store analytics, computer vision, supply chain, AI for merchandising or operations. If a retailer, a brand or a CPG company is your buyer, the sale runs on a calendar you don’t control, through a committee you can’t see, behind gates that were built to keep small vendors out. I’ve sold on that side of the table for thirty years — for small companies that became large ones, and for IBM, Adobe and Toshiba. This page is how that sale actually works, and what I do inside it.
Based in Scottsdale, Arizona. I work remotely with founders across the US and Canada.
A retailer doesn’t buy. A committee inside a retailer buys.
The VP who owns the problem — stores, eCommerce, merchandising, supply chain — starts it. Then the people who can stop it show up, usually one at a time and usually late.
- The business owner. Store operations, digital, merchandising or supply chain. They have the pain, the budget request, and rarely the final signature.
- IT and the CIO’s office. Architecture, integration, the roadmap you are competing with for engineering time. They decide whether you fit the stack or fight it.
- InfoSec and privacy. PCI for anything near a transaction. Shopper data, video, loyalty identity. A retailer’s security review is a gate, not a form.
- Finance and procurement. Vendor risk, insurance, the master services agreement, and a quiet preference for the vendor already in the building.
- The field. District managers, store managers, associates. If the rollout adds a step to their day, the pilot results will not save you.
- The partners. The system integrator, the POS vendor, the ERP or OMS incumbent. They are in the room before you are, and they decide who gets in the door.
Most emerging retail-technology companies sell the first person on that list and get surprised by the other five. Mapping all six before the pilot is the job.
Retail buys on a season, not on your quarter.
Every retailer runs the same year, and it decides when your deal can move. Sell against it and you lose a year without knowing why.
The founders who win know this by heart. They qualify in Q1, pilot in Q2, close the rollout before the freeze, and spend November building the next year’s pipeline while competitors wait for callbacks.
- JanNRF’s Big Show. The one week the whole industry, and every founder selling into it, is in one building. Meetings here set the year.
- Feb – AprAnnual planning lands. Initiatives get funded or don’t. If your project isn’t in a budget line by spring, you are selling for next year.
- May – AugThe working window. Pilots run, integrations get built, rollouts get approved. Most of your selling year happens in these four months.
- Sep – OctPre-holiday hardening. Store and eCommerce teams turn their attention to peak. New vendors slow down; incumbents get protected.
- Nov – DecCode freeze. Nothing new goes into a store or a storefront until January. Deals don’t die here — they wait, and the ones without a sponsor don’t come back.
A pilot with no decision date is a science project.
Retailers pilot everything. Ten stores, one region, one banner. The pilot is not the sale. The rollout is the sale, and the rollout has a different buyer, a different budget and a different set of objections.
What the pilot has to settle before it starts
- Who owns the rollout budget — and it is rarely the person who sponsored the pilot.
- What number, measured how, by whom, turns a pilot into a rollout decision. Agreed in writing before store one goes live.
- The decision date. A pilot that ends when the data is convincing ends never.
- The operational owner in the field. Store operations has to want it, or the results will be explained away.
- The integration lift IT is signing up for, and where it sits on their roadmap.
I have run this path from both sides — as the vendor selling the rollout, and inside the retailer watching vendors try. Most of them lose it between a successful pilot and a signature, in the six months nobody owned.
Built to keep small vendors out. Passable if you start early.
None of these are surprises to a retailer. They are surprises to the vendor, because the vendor met them one at a time, late, while the buyer waited.
- Security and privacy. PCI scope, SOC 2, penetration results, data residency, what you do with shopper video or loyalty identity. The packet exists before they ask, or you look small.
- Architecture. Where you sit against the POS, the ERP, the OMS, the data platform. Whether their developers will own your APIs or resent them.
- Procurement and legal. Vendor risk scoring, insurance limits, the MSA redline, references from retailers your size can’t name yet. Procurement’s path quietly favors the incumbent unless someone senior says otherwise.
- The incumbent. Ten years in the account and a VP who takes their call. They will not beat your demo. They will beat you on relationship and risk — unless you have a sponsor who will say the smaller vendor is the safer choice.
The difference between a founder-led company and an enterprise vendor is not headcount. It is that the enterprise vendor answered every one of these before the buyer thought to ask.
The same sale, at every layer of the retail stack.
I sold eCommerce and order management to retailers and brands at ATG, Demandware, hybris, Adobe, IBM and Kibo — small vendors that became large ones, and the largest brands in software. At IBM I closed the then-largest eCommerce and order-management deal in the company’s history, at Kroger.
At Toshiba I was Client Director for Kroger, badged inside the retailer’s own technology headquarters, running a $100M+-a-year book on point of sale and self-checkout. I have sat on the buyer’s side of the table and watched vendors sell — well and badly.
At Standard AI I rebuilt the go-to-market for a computer-vision company selling store analytics to enterprise retail through a product pivot, as VP of Sales reporting to the CEO. That engagement is why this practice exists.
Retailers and brands I’ve sold into
Where I sold it from
Fractional VP of Sales, built for the retail-technology sale.
The default engagement is fractional VP of Sales: I help you run the sales motion, and bring you in only where a founder is the difference. For a retail-technology company that means:
- An ICP written in the retailer’s language — banner, format, size, stack — and a buyer map for each of the six people who have to say yes.
- A pilot-to-rollout playbook with the decision criteria, the rollout budget owner and the date agreed before store one.
- The security, architecture and procurement packets built once, on purpose, before the first buyer asks.
- The partner and system-integrator motion — who gets you in the door, and what they need from you to want to.
- The RFP and RFI machine, so the response shows an enterprise company before you are one.
- A forecast built on committee reality — who has said yes, who hasn’t been met — that a board can believe.
- Your NRF week, planned like a campaign instead of a booth.
Retail technology, answered.
Do you only work with retail-technology companies?
No. The gate is a buyer that purchases through a committee, not a vertical. Retail, brands and CPG are where I am deepest, so this page exists. Manufacturers, distributors and other enterprise buyers run the same sale. Who I work with has the fit test.
What counts as retail technology?
Anything a retailer, brand or CPG company buys to run commerce or the store: eCommerce and order management, point of sale and self-checkout, store analytics and computer vision, merchandising and planning, supply chain and inventory, loyalty, payments, and AI applied to any of it. If the buyer is a retailer, it counts.
We have a pilot at a large retailer and it has stalled. Can you help?
That is the most common call I get. Usually the pilot proved the product and nobody owns the rollout decision — no budget owner, no decision date, no operational sponsor in the field. The fix is a late-stage job, not a demo job. Late-stage stalls are power-base problems is the longer answer.
How do you handle the holiday freeze?
By planning the year around it. Qualify early, get into the spring budget cycle, pilot in the working window, close the rollout before October. The freeze is when we build next year’s pipeline and sharpen the NRF plan. A founder who learns this once never loses a Q4 to it again.
Do you work with the system integrators and the POS or ERP incumbents?
Yes. I’ve worked with Deloitte, Accenture, Capgemini, Publicis Sapient and the other integrators who decide which vendors a retailer meets, and with the POS, ERP and OMS incumbents you will be selling next to. The partner ecosystem is part of the motion, not a separate one. I built Standard AI’s from scratch.
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. Services explains the shapes. You keep the decision rights.
Notes from inside these deals.
Most late-stage stalls are power-base problems
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 as partners in a complex enterprise deal. Three stages that need the founder, three that only feel like they do, and how Ed helps you run the difference.
When do you need a VP of Sales?
Founders keep asking me a version of the same question. The honest answer is usually "not full-time yet, but sooner than you think." That gap is where a fractional VP of Sales fits.
Thirty minutes. Bring the retailer deal that is stuck. Leave knowing how I’d tackle it with you.
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