How to Upsell to Existing Customers

Are you looking for ways to grow your revenue? Not sure when the best times are to upsell your customers? Then stick with me until the end of this article, because I’m going to outline three great times that I’ve learned from my experience to upsell your customers and do it successfully.

Good Time #1: Check-in calls with clients.

The first great time to upsell your customers is whenever you’re checking in with them. This can happen on whatever cadence you already do in your business, but most often it happens either on a quarterly basis, a biannual or an annual basis. It kind of depends on your particular niche. It can also occur though, on any set cadence that you and your customers have already established as good times to check in their goals with your product or service.

As you learn more about how they’re doing, what you’re going to want to do is come prepared with the data that you have about how they feel been using your particular product or service. And from there, you’re going to want to ask them if they’ve explored XYZ feature or ABC new thing that you have potentially been launching.

From here, we’ll begin to understand if there’s potentially an additional use case or an additional point of value that we can provide for our existing customers that may not be being delivered right now.

For example, let’s say that we had 50% of the users that our customer intended to be using our site, actually using our site. And there was another 50% that wasn’t yet onboarded on our site. So as a result, we might ask our customer, “Hey, what’s going on with that X, Y, Z users that haven’t yet activated?”

From there they might share with you that XYZ users are a little bit more hesitant with technology and they don’t really feel comfortable learning all these new things at once. So from this conversation, we could pick up that these XYZ users could really benefit from potentially some training or some formal time with our trainers to help teach them about all the benefits of our platform and specifically how our platform could help them save time in their day to day.

Oftentimes when you’re selling a SaaS tool or platform, you’re going to have a bucket of users that falls into users that are simply a little bit more hesitant when it comes to new technology. So from this conversation, there are two big benefits to our customer.

The first one is that we’ll take some of the stress off of them to train this group of lagging users, to get more educated and get more engaged with our service. And the second thing is we’re going to give them them even more value because once we activate this group of lagging users, we’re going to have even more happy users at this particular organization using our service.

It’s super important that as you have these conversations, you’re setting clear goals with your client as to what success would be measured by, by whatever the additional service is. In this situation, it might be something like, 25% more users on the site by the end of the year.

What gets measured gets managed. And so ultimately by helping our customers, think about the different ways that they can improve the results they’re seeing with our product or service, and then providing the options for them to make that actually happen. We are giving them a runway to achieve their particular goal.

Check in calls are one of the most natural ways to assess whether or not your company is delivering all the value that it can be delivering to your client.

Good Time #2: Key moments of customer momentum.

Another great time to upsell your customers is whenever they’ve experienced a key moment of customer momentum. What I mean by that is, it’s when your customers have experienced a major milestone in your respective customer journey.

Let’s say for example, that you’re a fitness instructor and that your client hired you for weekly training sessions, because they wanted to lose 20 pounds. Maybe they just hit 10 pounds loss and you only have two or three sessions left with them.

Well, it’s clear that they’re not going to hit their goal, but it could be an opportunity for you in your next session to pitch them on a bundle of training sessions in the next two months, because they just hit their halfway mark towards their goal. It creates a perfect storm, because your customer has already invested at this point in getting to their particular goal.  And they’re halfway to their particular goal.

So maybe this is a time for you as that instructor to pitch twice a week workouts, as opposed to just once a week and so on. The same thing applies regardless of whatever you’re selling. So you’re going to have these key moments in time where your customer has done something noteworthy that you can capitalize on in order to help them see even more value out of your product or service.

An example in the SaaS world is, whenever your customer actually reaches their cap in the number of users that are using the site. And so you can pitch them on more users or you might pitch them on a higher plan. It gives them more users. What’s clear in these moments is that the reason why your customers decide to work with you is no longer the extent of their actual need. So this is a supernatural way for you to upsell them.

What I want you to do is take a few minutes and think about what makes a super awesome user with your particular site. Or if you’re a product or service, what makes a super user or super customer for you?

This could be answered by thinking about what are the best actions that you always like your customers to do take, or what are the sorts of things that lead your customers to always ask you about additional training or services and different things that you sell? These are the moments that you want to capitalize on when it comes to upselling your customers.

Good Time #3: Ahead of major budgetary deadlines.

The third time that it’s really good to upsell your customer is way ahead of any budgetary deadline. Every single buyer has a timeline. So it’s on you to figure out when that timeline is. For example, in the public sector, some budgets open and close at particular points in time in a year.

And what that means is that if you’re coming into the conversation for a renewal with your customer, with an upsell, and they’ve got a week before they have to make a deal decision, otherwise their budget closes. They’re probably not going to actually buy it from your upsell. By taking a step back and trying to understand your customer and what their budgetary timeline looks like throughout the nature of your relationship with them, you can potentially identify better times to actually present your ideas for upselling with them.

For example, if you have a customer that has a deadline in December, you might want to reach out to them as early as September, because it might take a month or two to actually loop in all the relevant stakeholders to pitch the upsell idea that you have for your customer.

Making sure that you have enough breathing room for everybody to go back and forth with your proposal is crucial, especially when it comes to closing bigger deals. Too often, people don’t give their customers enough time to contemplate everything, and the best options for them in the following year.

And so, by taking a step back and understanding the timeline, we avoid the situation altogether, and again, create a situation in which we can have an upsell conversation in a more productive manner.

Big takeaways

There are two big takeaways from this article.

  1. The first one is that upselling is always easiest and low stakes conversations. If you wait until the last minute to make an upsell, you’re not going to have that many upsells be successful.
  2. The second thing is that upselling is really most successful when you’re focusing on bringing as much value as possible for your customer. If you’re just thinking about upselling, because you have to hit your quota or something selfish, then your client is going to see right through that.

And instead, what you need to do is ground yourself around, what value is my company giving my customer right now, and specifically how much more value can I exchange with my customer? Those are the opportunities where you’re going to find upsells are most natural, as well as most lucrative for you.

If you found this article helpful, be sure to check out my YouTube channel to get new videos every single week I’ll help take you from zero to self-starter as you grow your business, get more customers, and hone your business acumen. Also, feel free to share this article with anybody that you think might benefit from learning about better times to upsell their customers.

In the next article, I’m going to go over the five mistakes that I wish I had it made as a first time founder.

Get new videos

2X/week sent to your inbox!