Packing light is not my strong suit. Every trip, I swear I’ll only bring what I need — until I start packing and suddenly everything feels essential (yes, I need five different shoes for a weekend trip).

Your customers are the same way. They think they only need one thing…until they realize something else would make their experience even better.

This week in the PMM Camp community, a member asked:

Great question.

The best upsells don’t feel forced. They feel obvious. Like, “of course I need this, why didn’t I think of it myself?”

So today, I’m sharing three ways to identify expansion opportunities in your business.

The Art of Upselling

Upselling isn’t about slapping a “would you like fries with that?” onto every sale. It’s about recognizing when and why a customer might need more and making it a no-brainer for them.

There are three main ways to do this:

1️⃣ Customer Lifecycle Triggers – Finding natural upgrade moments in the customer journey.
2️⃣ Behavior-Based Signals – Using product usage patterns to spot expansion opportunities.
3️⃣ Best Customer Profiling – Identifying who’s most likely to buy more and why.

Let’s break them down.

Customer Lifecycle Triggers

Customers naturally hit key milestones where an additional product or upgrade makes sense. The trick is to find those moments and proactively offer the next step.

The key here is to understand the job your customer is trying to complete — and the smaller job steps within it. This approach looks at sequential actions (rather than time-bound actions).

Example: You work at a fitness app and see that users who complete 10 workouts are more likely to purchase a personalized training plan. You trigger an in-app offer when users hit this milestone.

💡 How to Apply It

Map out your customer journey and identify natural points where customers might solve one job and immediately need to solve another. Look at data on when existing customers tend to expand and build an automated playbook around those moments.

Behavior-Based Signals

Instead of waiting for a customer to realize they need more, use product usage data to spot signals that indicate a customer is ready for an upsell or cross-sell.

This approach works especially well when your company has a clearly defined value metric and looks at actions performed within a specific time-bound period.

Example: You work for a meal delivery service and see that customers who order three times in a month are more likely to subscribe to the membership. You offer a discount on the first subscription month right after the third purchase.

💡 How to Apply It

Work with your product team to dig into your product analytics. Are there any clear patterns where customers who engage in certain behaviors end up buying more? These are your best opportunities for automated nudges. (If you want to go deeper into this approach, the Reforge Product Growth Foundations course is a great resource).

Best Customer Profiling

Your best customers often hold the answers to who else is ready to buy more.

Shannon, a PMM Camp community member, recommended using the RFM model to analyze high value customers and find others like them.

Example: You work at a luxury skincare brand and complete a segmentation analysis. You see that customers who buy a moisturizer within a week of purchasing a cleanser have a 50% higher lifetime value. You create a post-purchase email flow recommending the moisturizer to customers who match the pattern and ICP criteria.

💡 How to Apply It

Take your top customers and analyze:

• Recency – How recently did they buy or engage?

• Frequency – How often do they use or purchase?

• Monetization – How much have they spent?

Then, look for customers with similar traits who haven’t expanded yet and target them with tailored upsell offers.

Remember, the best upsell strategy isn’t about pushing more products. It’s about offering the right value at the right time.

The key? Make your upsell feel like the next logical step. (Like that extra pair of shoes that obviously fits in your bag.)

What’s your go-to upsell strategy? Reply and let me know — I’d love to hear what’s working for you.

CAMPER ESSENTIALS

📚 Reading List: This week I received THE WORST price increase email from Netflix. My post on LinkedIn hit a nerve, and hundreds of people have weighed in. What’s your take?

🎧 Playlist: I don’t always have time to listen to The Tim Ferriss Show, but when I do, I always come away smarter. Episode 792 was no exception. Tim Ferriss and Seth Godin have a 2-hour convo about playing the right game and using strategy as a superpower. It’s well worth the listen.

🗓️ Events: Did I mention Day Camp? It’s happening March 11, and you don’t want to miss it. You’ll learn how to outsmart the competition and get heaps of Survivor puns. Register now for free!

Until next week,