Do you remember that classic 80’s movie Glengarry Glen Ross? It’s the real estate sales movie where Alec Baldwin coins the brilliant phrase, “First place is a new Cadillac. Second place is set of steak knives. Third place is you’re fired.”

Just once in my life I want to use that phrase.

In one scene, Baldwin completely loses his mind, screaming at the salesmen under him, “Always…be…closing!”

I’m going to pull an Alec Baldwin, minus the profuse profanity and constant challenging of everyone’s manhood.

But instead of saying, “Always be closing,” I’m going to say, “Always be upselling.”


Most sales funnels work like this. A potential customer clicks on an ad of some sort, which then drops them onto a landing page, which then leads to the actual sales funnel. Once in the sales funnel, they receive some sort of value, whether that’s an email sequence, webinar, strategy call, or something else. Finally, you move to close the sale. Once you’ve closed the sale, you move on to the next customer.

You got the sale, and that’s all that matters. Party on Wayne!




That’s all well and good…EXCEPT THAT IT’S WRONG!

If you’re not upselling after you make your initial sale, you’re missing out on a significant amount of money.

The best companies are always looking for opportunities to up sell customers. If you purchase a set of steak knives on Amazon, they’ll try to upsell you on knife sharpeners, plates, and other things only slightly related to steak knives. Before you even break out your credit card, Vista Print is trying to sell you calendars, t-shirts, and lame magnets.


Marketing guru Neil Patel recommends shooting for 30% of revenue coming from upsells. I want to help you get to that 30%.

In this article, I’m going to teach you how to upsell like a BOSS. I want to give you some tried and true, highly-effective methods for upselling, that, if followed, will result in dollars in the bank.

I’m going to give 3 tried and true methods, all of which work very well. I’ll give them to you in reverse order of my preference.

For the purposes of this article, I’m going to use the term “upsell” to any additional sales added on to the core sale. If you want a detailed explanation of upselling vs. cross-selling, check out this article from ConversionXL.



The proposal upsell happens on the proposal itself. When you submit the proposal to the client, you also include other services that would go well with what you’ve actually sold them.

A great way to make this work is by including hard statistics and case studies along with your proposal. For example, if you’re including Facebook advertising as part of your upsell, include stats about how many leads you generated using Facebook for “Carlos ‘No Fee Unless We Get Money For You’ Woodley, Attorney At Law”. If you’re including a site optimization upsell, include a case study about how faster load times leads to more web traffic which leads to more sales.




This has one serious psychological advantage: the buyer already has the credit card out and is in a buying mood. Psychologically speaking, they have crossed the purchase threshold that held them back from buying.  

However, you do have to be careful when doing upselling on the proposal itself. People don’t like feeling like they’re being sold, and the proposal upsell is about as blatant as it gets.

Additionally, you may end up creating a massive amount of extra work for yourself when the client comes back to you thoroughly confused. After all, if you didn’t talk at all about Facebook ads on the front end, they’re going to have zero clue what you’re talking about when you slap it on the proposal.

Remember, overwhelmed people don’t swipe credit cards. They shut you out.

The proposal upsell method is a solid option, but you need to tread carefully.




This is one of my favorite methods. Rather than try to work in a hard upsell on the proposal, I like to start soft upselling way before the proposal ever happens.

For example, a client who sells t-shirts wanted me to do some SEO work for them. We talked through their core demographics, their selling points, and the kinds of results they wanted to see. I brought up the subject of how awesome it would be to see them on Facebook. They’re a t-shirt company, after all, and apparel sells on Facebook. Look no further than TeeSpring or Threadless for proof of that.

As we talked, I gave them data and educated them on the value of Facebook advertising. I wasn’t hard selling them. I wasn’t being pushy. I wasn’t going used car salesman on them.

I was simply giving them value. When it was finally time for me to give them a proposal, they wanted to include Facebook advertising. My soft upselling long before the proposal made the actual upsell really easy.

When you talk to potential clients, give them data and educate them. Tell them about the specific successes you’ve had with previous clients using specific strategies and tactics. If you’re a web designer, point to case studies that show the value of having a video on the homepage. If you’re doing website optimization, give them data about the value of having a blazing fast website.

You’re not trying to push them into anything they don’t want. You’re not trying to bamboozle them or confuse them with smoke and mirrors. You’re upselling by way of education. You’re planting a seed in their mind which will fully bloom when it’s time for the actual proposal.




This is my FAVORITE method of upselling. Once you start doing this, you’ll really be upselling like a boss.

Your clients will, obviously, be very happy when you start hitting benchmarks for them. After all, if they see a spike in traffic or their business ranking higher in search results, they know that you can deliver results.




It’s then, when they’re happy with the results you’ve delivered, that you can most effectively upsell. Sending reports to clients is a great way of doing this. For example, you could send something like this:


Hey XXX,

Here’s your monthly report for the SEO work we’ve been doing for you. I think you’ll be really happy with the results! Not only are you ranking higher, but your web traffic is up 20%

I also wanted to let you know about some of the incredible success we’ve been having using Google Adwords to boost web traffic. Here’s a simple case study of how we doubled the traffic to Michelle Victor’s Dog Kennel website for only $500. If this is something you want to discuss, I’d love to talk further!



It’s crucial to map out your core services and your upsells. Your core services is the first, primary gear that turns. Once you hit a benchmark, you move to upsell them. You then fulfill the upsell, and which becomes a core service. This cycle repeats again and again.

Think, for a second, what this could do for your business. What if you did this with every client?


What would this do for your bottom line? An extra $40,000 maybe? Now are you seeing the power of upselling like a boss?




Sometimes upselling gets a bit of a bad rap. It’s considered a bit slimy or spammy, like a used car salesman’s trick.

But it’s possible to do upselling in a way that doesn’t manipulate your clients and creates significant extra revenue for you. It’s possible to have clients coming to you saying, “What can we do to spend more money with you?”

That, my friends, is what Michael Scott would call a win-win-win.




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