Selling to retailers

Retailers buy services when the margin math forces them to. Thin margins, seasonal peaks and a store footprint that costs money every day mean a retail executive won't fund anything that can't show up in the numbers fast.

Sell to that pressure and you'll get attention. Sell transformation in the abstract and you won't.

Who buys

In a larger retailer, technology spend sits with the CIO or CTO, but the money for most services work comes from the business. The chief digital officer owns e-commerce and the app. The COO or head of supply chain owns stores, distribution and inventory. The CMO owns loyalty and customer data.

The CFO matters more in retail than in many industries. With margins this thin, any engagement over a certain size goes through finance, and finance asks hard questions about payback.

In mid-size retailers it's simpler and harder at once. Fewer people, each owning more. A VP of IT might run the store systems, the warehouse and the website.

The pressures they face

Inventory is the big one. Too much ties up cash and ends in markdowns. Too little loses sales. A lot of retail technology problems trace back to not knowing what's where.

Then the blur between channels. Buy online, pick up in store, return anywhere. Every one of those promises needs systems that talk to each other, and in a lot of retailers they don't.

Then legacy. Point-of-sale, order management and merchandising systems in retail are often old and heavily customized. Replacing them is risky in a business that can't afford a bad holiday season.

And labor. Store staffing is one of the biggest costs a retailer controls, and pressure there pushes demand for scheduling, automation and self-service.

Signals that matter most in retail

Business pressure leads. Public retailers talk openly about margin, inventory and cost programs in earnings releases and 10-Qs. A line about markdowns or a new cost program is a direct opening. See reading an earnings release for the one line that matters.

New leaders are next. A new chief digital officer or COO arrives with a mandate and a short window to show it.

Then tech stack. Job posts in retail often name the order management or POS platform outright, and a cluster of posts for one platform usually means a migration.

And timing. Retail runs on a calendar. Change freezes before peak season are real. Big work tends to get decided early in the year and land before the holidays, or it waits a year.

An opener for a retail buyer

Say a regional apparel chain's latest earnings release mentions higher markdowns, and it just hired a new COO.

Saw last quarter's note on markdowns, a few weeks after you started as COO. That usually lands on operations first, since it's an inventory problem before it's a pricing one. My guess is stores and the website work from different inventory counts, so you're marking down product that's selling somewhere else. Is that the issue, or is it further up in planning?

Specific, about their business, and easy to correct. A COO who answers "no, it's the planning tool" has just told you where the work is.

What to avoid

Don't pitch in the fourth quarter. Retail leaders are heads-down from late summer through the holidays. A message in November competes with the busiest weeks of their year.

Don't lead with innovation. Retail executives have seen years of pilots that never scaled. They want to fix what's broken before they try what's new.

And don't forget the committee. A retail deal the chief digital officer loves can die in finance. Write to the CFO about payback and to the technical lead about cutover risk. Each of them needs their own reason to say yes.

Retail rewards sellers who understand the calendar and the margin. Show both in the first message.