B2B Upselling and Cross-selling 101

The surefire way to get more revenue from your existing client base is the magic of up and cross-selling. Let’s break down and unpack this beast so you can finally dip your toe into this never-ending pool of opportunity. Just so we’re all on the same page: Upselling is selling the something and making it better by selling something more with it. Like the cheese on the burger. Cross-selling is selling something plus adding on a something complementary to the product or service, like the fries with the burger. It makes it better, it makes sense and it serves the same purpose of easing the problem. Now let’s look at it closer.

Different Formats

There are several different ways you can structure upselling and cross-selling opportunities. Such as the Tiered Plan that represents varied levels of service. For example, I could upsell by offering my clients an additional Strategy Day to my largest package coaching clients. Equally, I could upsell a Sales Implementation lab for my smaller clients who have less time with me. Alternately, I could cross-sell VA services to my first Tier of clients and cross-sell an AI content creator software to my lower package clients. Another format is the Lifecycle one, where you create upsell and cross-sell opportunities as they come up within the customer journey of the client.


There is never a bad time to upsell or cross-sell. The timing can change from selling it in at the very start of the sales discussion, or at key milestones of client growth. You can upsell or cross-sell products or services ad hock, as a new program launch, or even as an ongoing ‘customer delight’ program. Lastly, you can do it as a time-limited offer during a promotion. The key is to just start thinking about the what and the how of doing up and cross-selling as soon as you can!

What to Sell

There are 2 sources of things you can upsell/cross-sell: Your own products and services or a partner’s. Either way, you’ll have to plan on which services can be bundled as upsells, which as cross-sells and what partner relationships and agreements do you need to create to be doing more upselling and cross-selling.

How to Start

I use the same process to figure out what to upsell/cross-sell as I do with finding super-niches in the market for my clients. You start with guessing at 3 of their most expensive, unaddressed industry or company challenges. Then you brainstorm as many products and services you or partners could have to help solve these issues. Next, you set up a series of short meetings with several key decision makers at the client end. The meetings will both serve as a status check up and to help you validate which of your 3 guessed pain points is the most top of mind one for them. The only thing left after that is to put together your upsell/cross-sell plan outlining what to sell and when to sell it to which customer.

You can wow your clients by showing them that you could be the solution to many of their unresolved issues, and you were right under their noses the whole time!

Want to reposition your messaging to grow your leads? Follow me on Twitter, friend me on Facebook, watch my Podcast on YouTube or connect with me on LinkedIn –and let’s talk.


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About Chala

Chala Dincoy is a Marketing Strategist who helps B2B service providers reposition their marketing message to successfully sell to corporate clients