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How to Upsell without Feeling Like a Pushy Salesman

by | Marketing, Sales Process

You got your business off the ground, and you have a steady stream of new customers coming in.

Congratulations! That’s an awesome start to building a solid business you love.

But the work doesn’t stop with the first sale. In fact, it’s just that sale is just beginning.

Your next job is to continue to make offers (and get sales) to your loyal customers. Remember, it’s much easier to sell to your current customers than to earn a new one, so don’t ignore those who have already shown they trust you.

So how do you make more offers without coming off feeling like a slimy salesman?  How do you get more sales without being pesky or pushy?

Never fear my friend, here are three stellar ways to offer an upsell product magically:

1. Create Step-by-Step Offers

For each of your services or products, create the “next logical step” for those who buy. If the first product was an eBook, then perhaps the next step is a video tutorial. If she’s already purchased your video tutorial, a multi-day workshop might be next on her agenda. And if that multi-day workshop was a hit, private, one-on-one coaching may be what she wants next.

By thoughtfully including “next step” recommendations in your emails and even in your products themselves, you can easily move your clients further into your sales funnel with timely upsells without feeling creepy or pushy.

You have to remember people will want to work more with you once they have bought from you, they want to go further, so you have to give them that opportunity. And they can’t buy what they don’t know about so don’t feel pushy about letting them know what else you have to offer them.

2. Automate Your Follow-Ups

Of course, it can be tricky to manage multiple products and services, so create an autoresponder series to follow every product purchase. You’ll want to include emails that encourage your buyer to use the products she’s already purchased, plus tips to help her progress even further once she’s done.

As she buys your next offer, make sure you make use of automation tools in your email software to move her from the “sales” list to the “buyers” list for that next product. When you manage this well, your clients will progress easily from one offer to the next.

3. Segment Your List

Be careful not to force buyers to make too big of a leap. The woman who bought your $47 eBook is not likely to sign on for a $1997 coaching program—at least not yet.

By segmenting your mailing lists, you can avoid making overly aggressive offers, and instead send your buyers precisely what they need when they need it.

Upselling your buyers is the key to higher income without more work. Don’t be afraid to make offers, and remember, a happy buyer is primed and ready to make another purchase. She’s counting on you to show her what’s next, so don’t make the mistake of thinking you’re bothering or annoying her by making offers.

Do it thoughtfully, and she’ll actually thank you for it.

Here’s to creating the life you LOVE!


Torie Mathis helps entrepreneurs get from where they are to where they want to be by working smart.  She is a best-selling author, Army veteran, speaker + trainer, and your mentor to creating the business+ life you love. She has cracked the code for creating a lucrative, independent business + an amazing lifestyle. She can help you with your marketing and business growth, your clarity and purpose and help you reach your vision of success. 🙂

Torie hosts SMART AF, a show for non-techy, non-marketers looking to grow their business, with her husband Sean and is the creator of SMART AF Magazine.


Best Small Business Marketing PodcastWhere underdog entrepreneurs go to get SMART AF about growing their business without wasting time, money, or sanity hosted by Torie Mathis.