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21 insights 💡 on upselling and cross-selling 


New here? This is Inbox Hacking, a Free Newsletter for Awesome email marketers eager to level up. Email marketing insights, tools, & tactics sent twice per week. Someone forwarded you our Newsletter? Please join over 14,793 Email Marketers and sign up for your Free subscription. Today’s edition→ sell more in hard times with these 21 insights on upselling and cross-selling.

Morning, Inbox Hackers. Closing in on the weekend has never felt better. Except that one time at a Thursday night Motley Crew concert in Jacksonville. Good times damage hearing BTW.

Let’s focus. There’s never been a better time to enhance your upselling and cross-selling skills. The economic sky is falling (perpetually🙄). So I’ve got 21 insights to help you make more sales with time-tested cross- and upsells. 

Upselling / Cross-selling 101

Basic definitions…

Upselling: offering an upgrade to original purchase.


Cross-selling: recommended complementary purchases to OG purchase.

Why bother with either?

#1 Insight: Upsells are 68% more profitable than acquiring a new customer (Optinmonster). Chasing is costly.

#2 Cross-sells make up 7% of e-commerce store visitors + account for over 26% of their revenue (Investpo).

Upselling and Cross-selling No-Nos

#3 Tread lightly. Being pushy doesn’t produce bonus sales. Being helpful does.

#4 Can’t be helpful without knowing what your customers want and need. So yes, you must wade straight through hell, aka gobs of data.

#5 Don’t look at upselling as giving away too much. Look for upgrades that cost you little time or effort, but impress your clients and give more value to customers.

Jeff’s Free Cross-selling Seminar

If you’re new to product recommendations, no worries. 

#6 At work? You already have an Amazon tab open I’m sure😁. Put a couple items in your cart and see how the pros do cross-selling. Also, check your old emails for Amazon’s pitches to buy related stuff.


#7 Keep it simple. Consider the most obvious cross-sells first then mind map your way to a variety of cross-selling opportunities. A/B test to optimize the process.

#8 What others have bought can influence shoppers. Adding a review next to these recommended items jabs the recommendations with steroids.💪🏼  

*Example Emails of Upselling here

#9 Vehicles for upselling and cross-selling:

  • Triggered and transactional emails
  • In-app notifications
  • Direct mail
  • SMS campaigns
  • 📦Packaging inserts

#10 Upsells and cross-sells should be no-brainer offers. 

Look, folks. If the client or customer has to think about it, it’s not a no-brainer. In case that’s not obvious.🧠

#11 When cross-selling, items well below the price of the original item work best. See #10.

#12 Deeper data hell. If you track average order value or customer lifetime value, then you should be able to track the payoff from product and service upgrades / recommendations. 

Not tracking those metrics? No worries, you’ll probably hit the lottery, and going out of business won’t matter 😅. Jokes, people.

Get Informed 

#13 Beg, borrow, or steal to get your audience to complete surveys so you’ll know what to cross-sell, what to upsell. 

#14 Begging not working? Look at services and items that don’t exactly fly off your shelves. That’s a concrete survey in my book.

#15 Read this post on the customer journey as an extra guide for audience needs.

Easy Sales

#16 Odds of upselling an existing client→ 60% – 70%, versus a 5% to 20% chance you’ll successfully pitch a new client (Marketing Metrics book).

#17 Repurposing content isn’t just for more content. How many useful guides could you create from past newsletters, then cross-sell in a sexier form? Or give away via vehicles in #9 above.

Timing is Everything

#18 The best time to upsell clients could be after they leave a positive review. Formal or informal, like a thank you card to your organization or phone call. Back to data – unless these positive interactions are tracked, you’ll miss a great shot at upselling.


#19 Monitoring your clients’ LinkedIn activity can reveal ideal times to introduce new offers to them. 

  • They land a phat contract
  • An employee your brand has worked closely with gets promoted 
  • The company expands their products and services

#20 Seasonal timing. But don’t wait until winter holidays to pitch related products to buyers. There are opportunities on a weekly basis. From the obvious lingerie recommendations with chocolate for Valentine’s Day, to not-so-obvious marriage counseling with those chocolates 36.5 months after the wedding😇.


#21 Finally, this Psychology Today article gives advice on avoiding impulse buying. Read it all if you wanna save money yourself (sky’s falling, remember). But use their third tip to ensure your upselling / cross-selling is successful.  

“Apply mindfulness to finance.”

If you make your upsell / cross-sell offers no-brainers, mindfulness won’t hurt your sales.

Knowledge Base

🔥Knowledge is power, but first, how to take the plunge.

Where website traffic originates (report highlights).

🧲Your first time doing lead magnets? Awesome examples.

Need help with email copy? 12 templates from Snov.

🥇Learn from successful mailers sending emails no one wants.


Imagine you pop open Gmail, and you have a long list of emails to go through. Classic.

A few seconds later, a new email pops into your inbox. Exciting.

Guess what? You’re way more likely to immediately open it rather than the long list of stale emails.

Inbox Mailers gives you this advantage. Rather than send an email blast to your entire list at once, you can send triggered emails when your subscriber is actively in their inbox.

This strategy can lead to open rates of 50% – 70% and improve overall deliverability. And, with better deliverability, you’ll see a higher sender score, better inbox placement rates, and improved overall email metrics. Test it for yourself…

Book My Demo

Demo Inbox Mailers

Self Help 

This HubSpot survey shows social platform growth patterns.

Whether you’re testing each new platform that comes out (i.e. BeReal) or focused on old faithfuls like Facebook, have a plan for protecting your brain.

Because even positive online social communities can drain your energy (ask anyone who’s built a successful membership site).

*Shout-out to Inbox Hacking Subscribers → 

🌞Lisa at SummerTimeMarketing

✏Yuval at Ackerman Copywriting

👩🏼‍💻Heather at LaunchTG (software)

Facts and Stats

  • 45% of email recipients say they “like brands that do not take themselves too seriously” (Snov)
  • Cybercrime predicted to reach $8 trillion USD in 2023 (Cybersecurity Ventures)
  • YOY, only 3 of 12 social media platforms saw decreased use by adults→ Reddit, Pinterest, YouTube (HubSpot)
Bonus: Adding a video link in an email can lead to a 200-300% increase in CTR.

From Our Sponsor

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This creates a virtuous cycle that boosts your reputation, deliverability, sender scores, and IP health — all at once.

Brands leveraging this technology are seeing 3x open rates! Plus, Inbox Mailers is also the best solution for re-engaging your inactive subscribers.

Book My Demo

Marketing Musings

Good news. Every time you think you’ve run outta things to say to your readers, you’re mistaken.

Proof? You’re still producing content. 

Also, take heart in the endless topics spat out by one of the most revered marketers ever.

Seth Godin blogs every day. His last 7 topics were:

  1. Freedom
  2. AI inventors being ignorant
  3. An anti-milk rant
  4. Being wrong
  5. Lack of nerve
  6. Bad systems and more bad systems 
  7. Getting the word in versus out

Topics and ideas are all around us. Most mean nothing. Until you make them mean something from your angle. 

Your angle is exactly what your readers need.

Get Hacking

Don’t freak out. Ah, go ahead, I’ll hold your hand.

About 23% of your list will decay over the next eight months.

Christmas will be here and oodles of subscribers will have become uninterested in your emails.

Others will have unsubscribed.

Today’s the day to prepare for that. You’re not helpless in this situation:

  • Improve sign-up forms – you need new subscribers to replace those leaving
  • Spot unengaged readers now to try to re-engage them 
  • Network with other mailers for partnerships that increase each other’s sign-ups

Get hacking. As you know, Christmas will be here in a flash. 

*Know another clever email marketer? Please forward this newsletter to them (thanks for reading).

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