TL;DR:

Personalization keeps customers comfortable, but managed serendipity sparks surprises, fueling more excitement, deeper engagement, and fresh revenue for smart loyalty programs.

For the last decade, the loyalty industry’s been banging the personalization drum like it is their job (and it is kinda.) Don’t get me wrong personalization is very important. Foundationally important.

And brands that get personalization right experience better buyer engagement, higher spend, and in some cases customers might even feel like getting a tattoo of their brand. Over 75% of shoppers say personalized offers make them consider a brand, and 80% are more likely to buy from brands that “get” them (McKinsey, BeBusinessed, IAGLoyalty).

But here’s the issue:

Personalization only reinforces the known.

It’s like your favorite restaurant serving you the same order, week after week. Predictable, safe, and eventually boring.

“The only true wisdom is in knowing you know nothing.”

— Socrates

(Not for nuthing but I’ll just bet you said Socrates with a long “a” sound like they did in the movie.)

Personalization is built on the assumption that we know our customers really well.

But is the smartest move to make to admit we don’t know everything about them—and that the real magic happens when we create room for discovery?

I think so…

So here’s my take: keep personalization, but bring in its wild and crazy friend—managed serendipity.

The Comfort Zone of Personalization

Let’s give personalization its due. Numbers don’t lie:

  • 76% say personalized comms make them consider a brand (McKinsey).
  • 80% are more likely to buy, and up to 44% say they’re repeat buyers after a personalized shopping experience (BeBusinessed, IAGLoyalty).

Still, personalization can turn into a closed loop—brands push more yoga pants because you clicked yoga pants. It’s safe. And…. predictable.

Enter: Managed Serendipity TM SM MM

(trademarked, service marked, Marky Marked)

a.k.a. Marketing With a Wink

Managed serendipity is planned surprise. Giving customers the “Whoa, I didn’t even know I wanted this” moment.

And it’s backed by data:

  • Rutgers Business School found that carefully curated, unexpected product recommendations left people more satisfied and willing to pay more than if they picked everything themselves (Rutgers summary, Rutgers paper PDF, ScienceDaily).
  • Subscription services that mix “you choose” with “we surprise you” see better product adoption and higher word-of-mouth.
  • Psychology research says surprise boosts curiosity, which makes us explore…and spend more (Neuroscience of Branding).

Translation: Serendipity isn’t just cute—it’s a growth lever.

The Mash Up

  1. Personalization → what you already love.
  2. Serendipity → stuff you didn’t know you’d love.

Where they overlap? Billiant success!!!

  • New revenue from unexpected products.
  • New engagement because people come back to see what’s new and next.
  • New ideas that open the brand’s thinking.

Don’t trust me… trust results…

  1. Random-but-relevant drops boosted willingness to pay by up to 30% over personalization alone (Rutgers, ScienceDaily).
  2. Surprise offers delivered 40% more “meaningful” brand experiences (Rutgers paper PDF).
  3. Companies mining for unexpected insights—not just the obvious stuff—had offers perform 50% better in A/B tests (Ask.com Marketing Guide, ScienceDirect).

How to Do It Without Creating Chaos

This isn’t about throwing personalization in the dumpster; it’s about seasoning it:

  • Slip one “wild card” offer into every loyalty email.
  • Add a mystery rewards tier.
  • Toss in products just outside the customer’s usual orbit.

Bottom Line

Personalization makes customers feel seen. Managed serendipity makes them feel surprised.

And as Socrates might agree, admitting we don’t know everything about our audience is the first step toward creating offers they can actually get excited about.

When you blend the two, you don’t just keep customers—you give them stories they want to tell about you.