7 Smart “Not-Pushy” Upsell Strategies for Beginners



Have you ever thought about using upsells in your business, but didn’t because you weren’t sure they would work?

Maybe you were even worried it might “annoy” your customers or clients...

Well I can tell you from first-hand experience that learning how to upsell transformed our business.

It’s a critical of reason why I was able to shift AutoGrow from selling services in 2017, to being focused on creating and selling our own products in 2018.

I think of us as a (born again? 🙃) startup for that reason. And as you may have seen, I’m always sharing the lessons learned with you along the way.

In the screenshot above for instance, that’s our gross (DISGUSTING!... "grow up Matt... just, grow up...") revenue from the last two weeks.

About 40% of that revenue came from upselling.

Significant, right?

While it may not feel realistic to achieve a 40% lift in revenue from upsells, certainly 15% is doable. By the way, upselling works just as well (even better in some ways) if you're selling services.

Still, you may not be convinced...

Well, consider this statistic from research shared by the authors of the book, Marketing Metrics, 2nd Ed.

  • The probability of selling to a new prospect is 5-20%. The probability of selling to an existing customer is 60-70%.

Powerful stuff.

And you can bet the top guys and gals in your market are getting an edge from upselling even if you aren't.

That's why today, I’m going to give you 7 simple upselling tips that will teach you how to do it right—even if you’re a total newbie to upsells.

  • If done right, using just one of the seven tips I’m about to give you is likely to grow your revenue by 10% or more.

Now, some people think upselling has to be “salesy” or comes off as “pushy.”

  • If you follow my tips, I’ll show you how to avoid that.

Others may also think it’s too complicated or too much work.

  • As I’ll teach you, it’s actually very easy because you can turn what you already have into an upsell. No need to create a new offer from scratch. There's a really cool strategy for doing this that most people don't know about...

First things first though, let’s start with the basics...

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What is an upsell?

An upsell is defined as an offer on top of an offer that has already been made.

An upsell can be an upgrade to something more premium or a complementary add-on.

The word is often used interchangeably with “cross-sell”. There are some technical differences between an upsell and a cross-sell.

Here’s the technical difference and a visual way to remember it:

  • An upsell is “UP” meaning, sold on a higher priced package or a more expensive service.
  • A cross-sell is “ACROSS” (think: to the left or to the right). This means a product or service that’s around a similar price point and that helps to solve the same problem or provides a relevant related benefit.

Note: If someone buys from you and you offer a product that has nothing to do with what they just bought, that’s not called upselling or cross-selling. That’s called killing your conversion rate.

So don’t do that ;-D

Ok so you know the difference between an upsell and a cross-sell.

Don’t get too hung up on the exact definition because it doesn’t matter that much.

What counts is growing your business by executing on the strategies and tips I’m about to give you.

If you want to compete effectively, you have to get serious upselling.

As I mentioned in the introduction, existing customers are up to 14 times more likely to buy from you than new customers.

Similarly, from my testing of existing email subscribers vs. new email subscribers: existing subscribers were 2X more likely to buy from us.

Further, out of the 3 main levers you have for growing your business, monetization (i.e. conversion optimization / maximizing size of the sale via upsells) has about a 4X higher impact on your profits than acquisition (traffic).

What does this mean for you?

Well, the data is quite literally saying that you can 2X your sales or more without growing your website traffic.

Upselling is one of the best ways to do that.

Here’s the first strategy...

Strategy #1 — Get comfortable with upselling.

You’re probably reading this article because you’re new to the idea of upselling.

That means you’re probably not doing it, or you think you could be doing it much better than you currently are.

I think the most common reasons someone won’t add upsells to their marketing funnel is the fact that:

  1. You’re too busy and think it takes a lot of work
  2. You’re concerned: “Will I annoy potential customers if I do it?”

I’ll address B for you right now. I’ll address A coming up.

Let’s back up a second and do a “gut check” ...

  • Do you believe what your business sells to people is valuable?
  • “How so?” you say.
  • Do you believe your product / service will make people's lives / businesses better?
  • “Well, of course!” you reply.
  • When you offer an upsell, will that offer be valuable too, like your current product or service?
  • “Yes… what are you getting at? ...”

If you believe your product / service is truly valuable, then there’s no reason to be shy about offering that value in the form of an upsell.

Think about it like this:

If you believe in the value of what you’re selling, you have a moral obligation to sell it.

After all, if you know it can make people’s lives better, then it’s only fear of trying something new that’s holding you back.

I remember when I went seeking advice on how to grow my agency about 5 years ago.

I was on the phone with an entrepreneur who owned a successful SEO agency.

I’ll never forget how he put clear terms for me:

You’re not f**king selling.”

If you’re not comfortable selling in the first place, you won’t be comfortable implementing an upsell. So get comfortable first, or make your product or service better.

Whatever it takes.


This next strategy addresses a common question...

Strategy #2 — To upsell at the right time — every time — leverage the “trust moments” in your funnel.

Last year I received a question from an audience member. That might be the same question you’re wondering right now:

When do you upsell? Where should you do it in your funnel?

I thought the answer was obvious, but it’s actually not especially if upsells, funnels, conversion, etc., are new to you.

I checked some other well-developed websites online selling products and services.

Almost none of them did this one simple thing that I was doing…

You see, there are what I call “trust moments” that happen in your funnel. Sometimes they’re hard to target because you don’t realize they’re there.

A trust moment happens when a potential customer takes an action within your sales funnel. That action is interpreted as their trust in you increasing, or decreasing. If it’s increasing, it’s a “trust moment”, and potentially a marketing opportunity.

For example, a common trust moment in almost every marketing funnel is when someone joins your email list.

In that moment, the person is saying:

I trust you, at least enough to optin to get your newsletter or this awesome lead magnet.

And you know that because people don’t put in their real email address unless they feel some assurance that you’ll protect their privacy.

So that is what I do in our sales funnel.

When people opt-in to our newsletter or one of our lead magnets, we redirect them to a landing page with an offer.

This offer is a tripwire, but you could also call it an upsell since the product we offer is relevant to the lead magnet they opted-in to get.

In this context, our tripwire is our first upsell because we’re converting email subscribers into paying customers where they get more value.

How can you leverage the same trust moment in your funnel?

What are some other actions that show trust, and therefore a good time to make an offer?

Strategy #3 — Short on time? Do a “product splinter” or “service slice.”

Creating your first upsell doesn’t have to be difficult.

Sure, you can come up with a brand new offer.

And if it’s a product, that will mean making a new product.

But the problem is that creating effective sales copy and graphics for an upsell is enough work.

And you want to see how well an upsell can work for your business now, not later.

The solution is “product splinter.”

Or if you’re selling services as I was for the first 7 years of my business, then do the same thing. But call it a “service slice” (especially because it sounds cooler).

A product splinter is to take a portion of your existing product and make its own, new product.

It’s so simple and it takes a fraction of the time to create something from scratch. Plus, you know it will probably sell if existing customers are already buying the main product.

Further, it’s an easy (logical) way to upsell to price-sensitive customers. For those who are on the fence, it’s logical to offer them your full product after they’ve tried the “splinter” version.

For example, I was able to create a new product almost overnight using this strategy.

I put together a free video training series on how to grow your traffic with content marketing. I wanted to make the most relevant offer possible, but we didn’t have one on traffic at the time.

Many people going through the training were already familiar with our Sales Funnel Blueprint course. But they were on the fence because of a pricing or relevance concern.

So, I “splintered” off some lesson modules from the Blueprint course, and created Triple Your Traffic.

It didn’t take me too long to create this new, more affordable product.

It helps customers who want to generate traffic without risking money on ads.

And of course, it gives the opportunity to upsell customers who buy it on the full version of the Blueprint course.

“If you like this, then you might like the full version which includes building a complete sales funnel to convert your traffic for an extra $100.”

That’s the basic pitch, and thanks to the product splinter it’s an easy, relevant, and logical one to make.

So far, about 33% of people who buy Triple Your Traffic have upgraded to the Blueprint when checking out.

If you’re selling services, the splinter (“service slice”) strategy works better.

When you’re selling high-ticket services like a $5,000 - $15,000+ service — that’s tough!

We were a website design agency in the beginning, and most conversations would go like this:

Me: Hi, we can do it, we’re awesome, we’ll redesign your website and it’ll make you look awesome. 😎

Them: 🤩Cool! How much?

Me: Just $10,000.

Them: 🤔

Me: And you only have to pay 50% now to start…

Them: Um yeah! Sounds great and all! I’ll think about it and never call you back but say I will anyway because honesty is awkward.

Me: 🤔…

What I didn’t understand back then was how to solve for their perception of risk.

When I created a service slice in the form of a Project Roadmap, I sold it for $300 each. That was a fraction of the cost of the full service.

Almost overnight we were making $1000’s just from selling Roadmaps!

And then the upsell to the full project was super easy. We’d already delivered value and established credibility. I even closed our first project for $30K during that time.

(Note: A Project Roadmap was a complete executable plan for how their website would be built.)

Any ideas for how to apply this “splinter” / “slice” strategy to upsell and grow your conversion rates?

Strategy #4 — Use an order bump as a cross-sell

An order bump is an instant upsell displayed at checkout. You’ve probably seen one of these in your journey through the interwebs…


You simply check off the box to add the “extra thing” to your order.

Order bumps are often impulse purchases because they offer something at a special price. Also, their value is complementary to the main product being sold.

We use an order bump with AutoGrow’s $7 tripwires. It works quite well, 12% of all customers add it to their order.

That number would be much higher except that the order bump offer is $97.

So 12% is pretty good. However, very possibly an offer for half that price would convert 3X better. I’ll AB test it soon and share the results in a future article if you’re interested.

What can you offer as an order bump at checkout?

Think: a simple, complimentary value-add.

Also, it’s fine if you re-use the same upsell offer that you also present in greater detail elsewhere in your funnel.

Strategy #5 — Use Urgency.

As you may have read above, upsells can be impulse purchases and include special discounts.

Urgency can come from a “fear of missing out” (FOMO).

According to professor Dr. Christopher Hodkinson at Queensland Business School:

"FOMO [is] most keenly felt when known others would attend a function or purchase a resource perceived as scarce.”

Urgency is often naturally built into an upsell, but it really depends on the context…

There are three types of upsells:

  1. Checkout upsells
  2. Post-purchase upsells
  3. Long-term upsells

When someone decides to buy something, it’s like a “door” that has temporarily been flung open in their minds. There’s a feeling of commitment, hope, and excitement.

For instance, I recently bought some “Blue Light Filtering” computer glasses since I work a lot on the laptop.


When I bought them, I was excited and hopeful they would work well (and they do actually). Though I think I’ll upgrade a better fitting pair down the road. My head is too big, no pun intended 😎.

Now if Amazon had offered me some kind of case to protect the glasses during checkout, I would have been extremely open to the idea.

I would have decided right then, probably...

That’s because checkout upsells are naturally urgent because you are committed to buying at that point. So, you will (probably) decide right then to add this “extra thing” to your order or not.

Now, I could have rationalized not to buy the case:

“Meh… let me see how the glasses work first and maybe get this later.”

But to change “probably” into “definitely”, they would simply need to add urgency. For instance, a 30% discount on the case, but only if I add it to my order now because ___insert reason___.

You can see how checkout upsells have some natural urgency. But you can make it more effective by offering a one-time discount, or by communicating urgency in the copy.

You can communicate urgency by saying something like:

“We recommend you add the case to your order since 50% of customers end up buying a case later on anyway, according to our internal survey.”

For the other 2 types of upsells “Post-Purchase” and “Long Term” — there isn’t much natural urgency because time has passed. The customer has the solution.

Still, existing customers are about 10X more likely to buy from you than first-time customers.

So, with a “Long Term” upsell you might offer some sort of customer loyalty special offer.

The two things these two types of upsells have in common is that you need to follow-up...

Strategy #6 — Deliver a relevant offer based on customer feedback via email automation.

That stat I quoted above, that existing customers are about 10X more likely to buy from you than new customers (who haven’t bought from you before) isn’t just theory.

It’s true.

For instance, when I launched our Sales Conversion Pack product about half of our customers for that were returning customers.

If you’ve ever spoken to any marketing consultant for more than 5 minutes, usually the first thing they’ll tell you is some version of that 10X stat, and that is something to focus on.

They aren’t wrong, but if they’re only looking to “juice growth” to prove something to you, be aware: it will work. The important thing is making it work for the long term, again and again.

Using email automation is the way to go.

In my detailed guide on Social Proof, I showed you how you could automatically gather social proof by surveying customers about a week after they bought.

When you confirm a customer is satisfied or happy with your product or service, you also know they are likely to open to another offer from you.

So for any customers who express satisfaction, deliver an upsell.

If you have multiple upsells, include an additional question in your feedback survey.

Ask what “problem” or “pain point” they currently have now related to the original problem your product or service addressed. Setup your email automation to send the most relevant offer based on their answer to this.

I personally use ActiveCampaign, though I’m looking at Drip for the future.

You can use retargeting ads in a similar way here. Email still works best, but I recommend combining the two for best results.

Strategy #7 — Amplify desire with social proof

It’s difficult to please everyone.

Upsells, especially checkout upsells, are destined to turn some people off.

Even though major businesses offer them, like GoDaddy…


And Amazon…


Some people still are uncomfortable with them.

So it’s all in how you present it.

Because you cannot create a desire to buy your product or service. You can only guide customers and do certain things to help them feel comfortable.

This is where social proof can help.

For example, I recommend using a “vanity metric” to show that a significant portion of other customers actually added your upsell.

Here’s how I did it for an upsell on our Proven Sales Conversion Pack product.


The 31% number is the metric, and it’s a subtle way of telling people:

Hey look, other people added this cool thing! And if other people took time to look thru the offer and then buy it, maybe it’s worth your time as well.

Bonus Strategy #8 — Embrace the downsell

What is a downsell?

A downsell is where you make an upsell offer to a customer and they reject it. So instead, you then offer a “downsell”. It is usually something less expensive, but that still adds relevant value based on their initial purchase.

Often it might be a “smaller package” version of the original upsell.

Sort of like a product splinter which I covered in strategy #3.

Why should you do this? And why do downsells work?

There are 3 main reasons why someone will reject your upsells:

  1. Perceived relevance
  2. “I don’t have time for this and the main product...”
  3. Price

If your upsell is offering relevant value that amplifies or complements the original product being sold, it’s probably an issue of time or price.

A downsell works to address customer’s the price concern.

For instance, if you’re buying a coffee maker, the upsell might be offering you to upgrade to the “premium coffee bundle” for $197 more.

It includes

  • A sack of premium, imported coffee beans...
  • A higher-end version of the coffee maker…
  • And, an awesome Contigo mug to keep your coffee nice and toasty warm all day long….

WOW! What a deal…

But you hit REJECT  😓

Why would you do that?!

Well, maybe $197 was too much.

So then they offer you the “basic coffee bundle” for $67:

  • Sack of imported coffee beans and...
  • A premium, super awesome Contigo mug



As you can see, the downsell was the same offer, but at a lower price point and some of the value subtracted.

One of the easiest ways to offer a downsell (and upsells in general) is SamCart. I use and recommend them. We’re also affiliate but I’d recommend them regardless.

Here’s how one of the upsell / downsell funnels we’re testing is performing right now.


What ideas can you think of for a simple, clear downsell in your funnel?


There are a limited number of ways to grow your business.

Increasing the average value of your existing customer or client relationships is one of the easiest and most effective ways to grow.

Upselling helps you do this by increasing the size of the average transaction and increasing the lifetime value of each customer.

There are some subtle differences between upselling and cross-selling which we went over, but many marketers use the words interchangeably.

The important thing is to apply one or more of these strategies to grow your business:

  • Strategy #1 — Get comfortable with upselling.
  • Strategy #2 — To upsell at the right time, every time, leverage the “trust moments” in your funnel.
  • Strategy #3 — Short on time? Do a “product splinter” or “service slice.”
  • Strategy #4 — Use an order bump as a cross-sell.
  • Strategy #5 — Use Urgency.
  • Strategy #6 — Deliver a relevant offer based on customer’s feedback via email automation.
  • Strategy #7 — Amplify desire with social proof
  • Bonus Strategy #8 — Embrace the downsell

Some consider upselling an advanced strategy, and if you’re a startup just getting off the ground that may be the case.

You can still benefit from planning your upsells as you build out your sales funnel in either case.

Speaking of which, you might like our training on the subject, the 6-Figure Sales Funnel.

Now, tell me what you think...

Do you believe upsells can grow your business?

Which strategy or tip did you find most relevant?

Leave a comment below, I’d love to hear from you and I read and reply to each one.

And if you enjoyed this article consider sharing it on Facebook, LinkedIn, and Pinterest.

Keep convertin’, stay focused,



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