Retail media has a structural tension most retailers are still working through.

Merchandising optimizes for retail margin.

Retail media optimizes for ad revenue.

Search platforms optimize for relevance.

But when those systems operate separately, who actually controls what surfaces on the page?

In this episode of The Middlemen, Tom Limongello and Scott Messer sit down with Andreas Reiffen, founder of Pentaleap, to explore the conflict between paid and organic ranking in retail search. They discuss why “rip and replace” migrations often fail, how multiple demand sources are entering the same grid, and why a unified ranking model based on compound margin retail plus ad value may represent the next stage of retail media maturity.

If retail media is going to scale without hurting retail performance, someone has to decide how the grid gets ranked.

This episode explores what that future looks like.