Personalizing your CX without SWEATING ??

Hi Squad!

This newsletter comes from flight AA 2204, the red-eye heading back from LAX to PHL. I got here Tuesday late afternoon for some quick meetings and a lovely Yotpo lunch & learn yesterday.

Fun fact: I tell myself that I prefer a red-eye flight over losing a full day of awake time in row 17F. But I am questioning some life decisions now.

Lots of exciting things are coming in the coming weeks. Another Empath Club dinner, the first-ever retention conference (I’d love to see you there), and more.

Alright, stop me from rambling; let’s hop into today’s topic.?

Personalization in the retention space is widely spoken about. Personalization in CX is often regarded as a waste of time and something folks only do if they can quantify the results. Let’s skip over that debacle, though,? and allow me to give you four straightforward ways to personalize your CX and deliver phenomenal experiences without sweating an extra iota.

Alright, let’s dive in.

This week’s newsie is brought to you by Siena AI !

This week, we’re spotlighting Siena AI , the pioneer and category creator of Empathic Autonomous AI Agents.

I'm not one for typical ad reads, but I've gotta tell you about the cool stuff Siena's been up to. They're constantly shipping new features based on what their community actually needs. Here are three that caught my eye:

What Makes Siena Stand Out:

• Siena Copilot for Kustomer and Zendesk: This helps your human agents craft better responses. When full automation isn't possible, agents input context and get AI-generated replies. It's like having an expert assistant for every interaction.
• Loop Returns Integration: Siena now handles the entire returns process in chat - initiating returns, sending labels, processing exchanges, and giving status updates. It's making returns way less of a headache.
• Custom Integrations: This is a game-changer. Just like you'd train a new agent on your tools, Siena needs access to your unique tech stack. Now, you can create code-free integrations for any tool you use. Siena can pull info and take action based on your instructions, fitting perfectly into your existing workflow.

Some recent fantastic webinars on the success stories:

• Madhappy : “The one thing I'll leave everybody with is if you're apprehensive about AI, just test it out. I have not seen a single person disappointed by it. And I know besides ourselves, I know a number of companies using Siena and I've not heard one person have a bad experience with it. It will definitely change your customer service department for the better.?

- Todd Baxter, COO Madhappy

• Simple Modern : “It's really difficult to tell that Hallie is not a real person for folks. I don't feel morally compromised in that. Customers are happy. We're happy and more efficient. They're getting a better customer service experience than they would have otherwise, frankly.

— Burke Lewis, Director of Ecommerce at Simple Modern

• Bandit : "I'm very happy to say that CSAT for Siena is consistently a 5."

- Emily Shaw, Head of Operations at Bandit

What I love is how Siena co-builds with their users. It's not just another tool; it's like they're part of your team, constantly evolving to fit your needs.

Siena is offering my readers an exclusive 3-month free trial and free access to the Certification Program. Just hit up their team and drop my name, Eli Weiss.?

Book A Demo Here

Okay, here are some ways you can personalize your CX without breaking a sweat.?

1. Personalize Support Interactions with Contextual Data

One of the quickest wins in CX personalization is using contextual data to enhance support interactions. When a customer reaches out for help, having immediate access to their purchase history, previous interactions, and preferences can turn a standard support ticket into a personalized experience.

95% of helpdesks offer this out of the box; they just don’t offer the patience and “giving a sh!t” you and your team need to do this well.

For example, if a customer contacts support about an issue with a recently purchased product, your support team can see their purchase history and any previous support tickets.

This means they can skip the generic “How can I help you?” and go straight to a more personalized response like, “I see you recently bought X—are you experiencing an issue with that?”

Unfortunately, though, we have been so infatuated with macros for every instance that we have lost the tiny pause it takes to take an interaction from menial to magical.

2. Automating Personalized Interactions with Multi-Source Data

Data is cool and all, but it’s how you use it that sets you apart from everyone else.

One of the simplest ways to personalize CX without burning out your team is by pulling data points from different sources—think return history, loyalty data, etc—and feeding them into one view.

It sounds fancy, but it’s easier than it seems.

With tools like Siena, you can plug in all this data to create interactions that feel personal without anyone lifting a finger.?

To give you an idea of what this could look like:

A customer with a high loyalty tier reaches out about a return. Instead of a generic response, the AI recognizes their value and automatically offers them an exclusive $10 bonus store credit if they choose exchange instead of return.?

No human was required, but it feels like there was.

This is where you stop thinking about automation as “impersonal” and start realizing it can make your customers feel like VIPs.

Oh, and if you’re already using platforms like Yotpo or Loop Returns, it gets even better. You can set up custom actions based on specific triggers—like a customer’s number of redemptions or return rates—so that every interaction feels as thoughtful as you’d scripted.

So, while you’re sipping your third coffee of the day (I pray it’s decaf), the system ensures your customers feel like they’re your only customers.

3. Leveraging Notifications for Positive Customer Moments

We love a good alert system for potential issues—whether it’s fraud, chargebacks, or delayed shipments. But what if we flipped the script and used that same energy to set up notifications for the positive stuff?

Here are some examples of moments where you can genuinely surprise and delight your customers, turning blah transactions into memorable experiences.

Celebrate Loyalty Milestones:

Set an alert in Shopify Flows or your loyalty program of choice every time a customer hits a loyalty milestone—whether it’s a certain number of purchases or reaching the top percentile of AOV.?

When that alert triggers, you could automatically send a super personalized message, a surprise gift, or even a handwritten note to thank them for their continued support.

Proactively Manage Delays with Personalized Updates:

Shipping delays happen, and they can be frustrating for customers. But instead of letting that frustration build, why not set an alert for orders that have been in transit for more than a certain number of days??

Using tools like Wonderment or PDQ, you can automatically follow up with customers before they even have to ask, offering them an update or even a small compensation for the inconvenience.?

This proactive approach can turn a potentially negative experience into a positive one, showing customers that you’re on top of things and that you give a sh!t about their experience, not just their money.?

Recognize High-Value First-Time Customers:

Another great use of notifications is recognizing high-value first-time customers. Set an alert for when a customer’s first purchase exceeds a certain amount.?

This could trigger a follow-up email or a special offer for their next purchase. It’s an easy way to acknowledge their value from the get-go and encourage repeat business by making that first experience feel special.

A fun variation of this is setting an alert for folks from an area you are familiar with so you can shoot a more personalized quick note. Matt from Huron often pings folks who live near where he grew up in the Midwest; it makes the world feel smaller in a beautiful way. ??

Automate Celebratory Messages for Customer Anniversaries:

Set up an alert for customer anniversaries—whether it’s the anniversary of their first purchase or the date they joined your loyalty/subscription program.?

When that date rolls around, the system can automatically send a personalized message and a special offer or reward to celebrate the occasion. Something demure. Something cutesy and mindful.?

4. AI That Reads Between the Lines

Let’s be real—understanding customer sentiment is an art form. You’d have to read between the lines, guess the mood, and hope you didn’t miss something crucial.?

If we are being honest, so much of this is cultural, too. Understanding the nuance of expectations, desires, and passive-aggressive slang of a US customer is very much not like a customer in Turkey or Tokyo.?

I’m not going to lie; for years, I’ve sworn off outsourcing my CX to somewhere outside the US for this exact reason. When AI came around, I was initially hesitant, but I got much more comfortable once I saw how great tools like Siena have gotten at just that. They are not like an outsourced team; the bots are like 100 Elis (equally terrifying and beautiful at the same time.)

Great AI doesn’t just take what the customer says at face value—it interprets tone, sentiment, and underlying emotions.

Are they frustrated? Are they ecstatic? Siena can pick up on those cues and tailor its response to match the customer’s emotional state.

Imagine a customer sends a polite message on the surface, but you can tell there’s frustration simmering underneath. Instead of a standard “Thanks for your feedback,” the AI can acknowledge the disappointment, apologize if needed, and offer a solution that feels personal.?

In a world where so much communication is automated, having AI that can “read the room” and adjust accordingly is what will set your CX apart.?

It’s not just about what you say, but how you say it—and now, you can make sure that “how” is always on point.

That’s it for this week!

Any topics you'd like to see me cover in the future?

Just shoot me a DM or an email!

Cheers,?

Eli ?? P.S. Looking for inspo on your next email/sms campaign? I know you will love this .?