Lessons from a decade of holiday retail media at Overstock and Bed Bath & Beyond.
There’s nothing quite like working in retail media during the holidays.
During my time at Overstock and Bed Bath & Beyond, Black Friday and Cyber Monday were consistently some of our biggest revenue opportunities. They were also some of the most operationally challenging weeks of the year.
More advertisers. More campaigns. More promotions. More pressure to drive incremental revenue.
And somehow, the same number of people expected to make it all happen.
Looking back, the holidays had a way of exposing every weakness in our retail media operation, from manual workflows and inventory visibility to competing priorities between merchandising, marketing, and media.
Here are four lessons I learned the hard way.
Every holiday season, we’d see an influx of suppliers wanting to advertise. Some were existing partners increasing their investment. Others hadn’t spent a dollar with us all year but suddenly wanted visibility during the biggest shopping days.
Great for revenue. Not so great for the team responsible for executing it.
We weren’t getting additional headcount to accommodate the demand. Meanwhile, creative was changing constantly, promotions were being added or adjusted, and featured products were selling out faster than expected.
A supplier would run out of inventory on a featured SKU, and suddenly we needed new creative, new approvals, and someone to make the changes before we wasted valuable impressions promoting something customers couldn’t buy.
Multiply that across dozens of campaigns, and you can imagine what our days looked like.
The lesson? You can’t scale retail media by simply asking your existing team to work harder.
If I were approaching holiday planning today, I’d prioritize self-service capabilities, standardized campaign packages, automated workflows, and better inventory visibility.
And I’d make sure we had backup products and creative approved before the campaigns went live.
Things will always change during the holidays. The goal isn’t to eliminate the chaos entirely. It’s to build an operation that can handle it without every change becoming an emergency.
As the holidays approached, the pressure from leadership to drive additional media revenue intensified.
The question was always some version of: What else can we sell?
And we’d get creative.
We’d identify unsold placements, package together remnant inventory, and go back to brands with additional opportunities.
Sometimes those packages made perfect sense. Other times, they came with trade-offs that weren’t always obvious when we were focused on hitting our media revenue targets.
For example, what happens when retail media wants to sell a homepage placement that marketing had planned to use for a broader category promotion?
That category promotion might have driven sales across dozens of brands. But now we’re considering giving that real estate to a single advertiser willing to pay for it.
Which option actually creates more value for the retailer?
The answer isn’t always the one that generates the most advertising revenue.
One of the biggest lessons I learned was that advertising inventory isn’t free just because the retailer owns it. Every placement has an alternative use, and during the holidays, those trade-offs become even more significant.
Retail media teams need to be thinking beyond what a placement is worth to an advertiser and considering what it’s worth to the retail business as a whole.
The holidays create a particularly challenging dynamic for suppliers.
Retailers are running aggressive promotions to capture demand. Merchants are asking brands to help fund those discounts. And retail media teams are asking those same brands to increase their advertising investment.
At Overstock and Bed Bath & Beyond, this was a constant conversation.
We wanted suppliers to participate in promotions AND invest in media to drive visibility for those promotions.
But that wasn’t always realistic.
Brands were already absorbing margin pressure from discounts, and many were being forced to decide where their limited budgets would deliver the greatest return.
Meanwhile, our merchandising and retail media teams weren’t always approaching those conversations together.
We were effectively asking brands to make two separate investments without always connecting them to one commercial strategy.
This is where merchant and media alignment becomes critical.
Rather than independently asking suppliers for more money, retailers should be coordinating promotional and media planning around shared objectives.
What products are we trying to move? What’s the margin impact of the promotion? Where could additional media investment meaningfully improve the outcome?
Sometimes the right answer is more media. Sometimes it’s shifting spend toward higher-margin products. And sometimes it’s recognizing that the supplier has already made a significant investment.
The goal shouldn’t be to extract every possible dollar from a brand during Q4. It should be to help them make investments that drive profitable growth for both businesses.
This one still gets me.
We’d spend weeks leading up to Black Friday and Cyber Monday encouraging brands to increase their Sponsored Products budgets.
We knew traffic was going to spike. We knew shoppers would be actively searching and buying. And we knew brands with sufficient budgets would be better positioned to capture that demand.
Yet every year, we’d see advertisers exhaust their budgets during peak shopping periods. Sometimes surprisingly early in the day.
Imagine preparing for the biggest shopping weekend of the year, only to have your campaign stop serving while customers are still actively shopping.
All because your budget wasn’t prepared for the increased demand.
Some brands listened to our recommendations and increased their budgets. Others didn’t, and missed valuable opportunities.
The lesson wasn’t simply that brands needed to spend more. It’s that we needed to do a better job helping them understand the opportunity.
Historical traffic patterns, category demand, campaign performance, and budget pacing should all inform holiday investment planning.
And once campaigns are live, advertisers need visibility into how quickly they’re spending, when they’re at risk of running out of budget, and where additional investment could make sense.
Because there’s a big difference between asking a brand for more money and showing them why that investment could help them capture more sales.
Looking back, most of our biggest holiday challenges weren’t exclusively retail media problems.
They were coordination problems.
Merchandising was managing promotions, inventory, and supplier economics. Marketing was managing the customer experience and promotional calendar. Retail media was managing advertiser demand, campaign execution, and revenue targets.
And our suppliers were trying to navigate all three.
When those groups weren’t aligned, the problems became painfully obvious during peak shopping periods.
It’s something I think about often in my role at Zitcha today.
Retail media has come a long way since I started building the program at Overstock, but many of the underlying challenges haven’t changed. The difference is that we now have better technology and more opportunities to connect media operations with the broader retail business.
A record-breaking month for retail media revenue doesn’t necessarily mean it was a record-breaking month for the retailer.
And that’s ultimately the lesson I took away from all those Black Fridays and Cyber Mondays.
Holiday readiness isn’t just about booking more campaigns or bringing in more advertisers. It’s about having the right people, processes, and visibility to turn increased shopper demand into profitable growth for everyone involved.
Because retail media shouldn’t just perform well during the holidays. It should help the entire retail business perform better, too.
Katie Carlson is Customer Success Director, Americas at Zitcha. If you’re working through any of these challenges ahead of peak season, let’s talk.