8 Strategies for Cross-Selling and Upselling Your Current Clients

| By: Geoffrey Willison

One of the most effective ways to grow your business is by expanding your services with your current clients. They know you, so the cost of upselling or cross-selling an existing client is much lower than acquiring net new business. In adopting this strategy, you can expect a much higher response rate because you've already established a relationship with these decision makers. And since they already understand and buy into the value of your managed IT services, it’s a much shorter sales cycle!

If you're looking for quick wins and easy growth, here are some strategies that will help you cross-sell and upsell your clients.

Just to make sure we’re on the same page, let’s define cross-sell and upsell.

Upsell: Selling a higher level of service to customer or prospect. For example, you have tickets to a football game and they send you an offer to upgrade your seats to the club level for a discounted price. That would be an upsell offer.

Cross-sell: Selling a different service of yours to a customer or prospect. For example, you have tickets to a football game and they send you a notice that jerseys are on sale for that game day only. That would be a cross-sell offer.

With these terms more clearly defined, let’s talk about some strategies for effective cross-selling and upselling.

8 Cross-Selling and Upselling Strategies

1. Start With Your Best Customers

It’s never easy to roll out a new service to everyone at the same time. There’s a learning curve and adjustments need to be made to your strategy before you approach all of your clients.

Try it out on a few of your most loyal clients first. Ask them what they think of the service, how it will impact their business, what they’d be willing to pay for it, etc. This is valuable feedback that you can then use when approaching other clients.

It’s always nice to have friendlies on your side that can provide honest input. Starting with your most loyal clients is a good way to get that feedback.

2. Perform Quarterly Business Reviews

We’ve talked about the importance of performing quarterly business reviews (QBRs) frequently on our blog. One of the reasons they’re so crucial for the profitability of your business is because they offer the perfect opportunity to cross-sell and upsell current clients.

Any salesperson will tell you that the key to selling is understanding the client’s needs. Cross-selling and upselling are no exception.

Understanding a client’s needs will help you appropriately position the new/additional service. Since you already discuss their business pain points and desires in QBRs so as to plan ahead for the upcoming quarter, these frequent business reviews naturally lead to cross-selling and upselling conversations.

You don’t need to close the deal during these meetings, but they should allow you to begin a sales dialogue. Don’t miss out on that opportunity.

3. Create a Customer Case Study

If you have a customer that is successfully using one of your products or a higher service level, capture their story in a case study. It’s always more effective to show real-life examples than to speak in theory. Gathering testimonials and repurposing them into customer case studies is a great way to do this.

Once you have completed your case study (let’s say for a client who just implemented your MDM solution), send it around to a few other clients who you think would also benefit from MDM. This could be done in a simple email offering a link to the case study, like this:

Hi [First Name],

One of my other clients, Bob’s Doctor Office, just rolled out mobile device management to help them maintain HIPAA compliance. You can read their case study here.

I think this would be a good solution for you to think about as well. Let me know if you’d like to chat further.

Best, [Your Name]

The email messaging doesn’t have to be too detailed, but it’s important to feature that case study as an asset. It comes across as helpful, rather than sales-y, which can make all the difference.

If you can’t get a full case study together, at least try to get a quote from your client or ask if you can use them as a reference. Their positive review will go a long way in helping you cross-sell and upsell other clients.

4. Write a Blog Post on the Topic

Writing a blog post on a topic related to the cross-sell or upsell can help re-emphasize the need for you solution. For example, using the above scenario, perhaps you create a blog post titled, "Why Every Doctor’s Office Needs Mobile Device Management," in which you explain specific reasons why MDM is so essential in healthcare IT.

If I’m a medical professional and after reading this post realize I don’t have a BYOD policy in place, I’m most likely going to explore your website and blog, browsing more of your helpful content. Pro tip: Offer the case study described above as a follow-up call to action for the post.

Just like the case study, you can share your blog post with some of your healthcare clients and see if they’d be interested in chatting with you further about MDM and the implications of not having a BYOD policy. Again, this comes across as helpful, rather than a sales pitch and people are much more likely to engage with you.

5. Offer a Trial

Sometimes all your client needs is to test your solution out, and offering a trial is an easy way for them to do that.

Let’s take Bob’s Doctor Office again. Say Bob’s secretary, we’ll call her Janice, is always calling you because she forgot the Wi-Fi password or just can’t seem to figure out how to use Outlook the right way. I know Janice is the sweetest lady and bakes you delicious double chocolate chunk cookies for the Holidays, but frankly, you’re just sick of her calling every other day with an issue.

Instead of fielding each of these noisy requests, why not offload Janice’s support calls to an outsourced help desk? However, what if Janice adores you as her IT guy and may not want to call someone else for help? Letting her try out your help desk allows her to overcome her initial resistance and become comfortable before fully committing.

Trials may cause you to eat some cost up-front, but will ultimately make you money in the long run and can be a very effective upsell and/or cross-sell strategy.

6. Offer a Discount or Incentive Program

If a trial isn’t applicable or reasonable, try out a discount or incentive program. Perhaps you offer clients three months of service free if they commit to a year of mobile device management. Or maybe you throw in MDM for free if they upgrade to a higher service level.

Obviously, you’ll need to figure out the ROI of the offer, both for your client and for your own business. Make sure the numbers make sense then test some of the offers out with your clients. See which ones get responses, start the best conversations and ultimately lead to deals.

7. Tell Them They Need

It Sounds simple enough, huh? While it may not be as easy as calling up a client, telling them they need your new business continuity solution and then rolling it out the next day, confidence does go a long way in these situations.

Your clients have trusted you to handle their IT needs because you are the expert. You need to tell them what they need.

If a CIO were to say, “I need more budget so that we can implement a backup and disaster recovery (BDR) strategy” and he/she could clearly articulate why a business continuity solution was important, there’s a much better chance they'd secure the budget vs. asking, “Could I have more budget for a BDR tool?”

This approach establishes a need instead of a want. Be confident, clear and articulate in your argument, instead of asking if they’d be interested in learning more. When you tell your client what they need directly, you stand a higher chance of closing the upsell or cross-sell, while establishing yourself as their “Virtual CIO.”

8. Sales Team Incentive Plan

This might not be applicable for all MSPs, but those with a few salespeople or a full sales team need to make sure those individuals are incentivized to upsell/cross-sell. Most sales people are driven by competition and compensation; use these as motivators to increase your sales.

For example, run a competition for who can sell the most MDM licenses in a quarter and give the winner a bonus and/or a prize. Start a leaderboard in your office that shows exactly how team members stack up against each other, or one that measures the team’s progress towards the quarterly goal.

There are many ways to incentivize sales people; however, many people forget about sales incentives when running their upsell/cross-sell campaigns.


Don’t miss out on the opportunity to cross-sell/upsell your current clients. It can be one of the easiest ways to increase revenue and grow your business. While there’s no one-size-fits-all strategy for doing this, the above guidance should help get you thinking about how you can start building campaigns for your current clients.