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From One-and-Done to Cross-Sell: Train Your Reps to Sell More

Sales leaders: Use AI-powered tools to help reps stay updated, conduct deep discovery, and follow your playbook to boost cross-sells and advance deals.
SKO done, adoption none!
Sanchit Garg
Sanchit Garg
Cofounder & CEO, Zime
Published Sep 11, 2024

Intro

Cross-selling—sounds tough and serious, right? But it doesn’t have to be! In fact, when done right, it can be one of the most rewarding (and fun) parts of sales. The problem? Too many sales teams misunderstand it or find it tricky, which means missed opportunities and customers who might not be getting the full experience they deserve.

In this blog, we’re going to flip the script on cross-selling. We’ll bust some myths, tackle the common challenges head-on, and introduce you to Zime—a nifty AI tool that’s here to make cross-selling as smooth and straightforward as possible. Whether you’re a sales leader or a sales rep, you’ll walk away with a fresh perspective and some great tips to boost your sales game with AI.

Ready to make cross-selling not just effective, but actually enjoyable? Let’s dive in!

Difference between cross sell and upsell
Difference between cross sell and upsell

2 misconceptions about cross selling & upselling

Cross-selling and upselling is often misunderstood or underestimated by sales teams, leading to missed opportunities and untapped revenue potential. Two common misconceptions about cross-selling are:

Cross selling or upselling is pushy and annoys customers

Many salespeople believe that cross-selling comes across as aggressive or manipulative, potentially damaging customer relationships. However, when done correctly, cross-selling demonstrates a deep understanding of the customer's needs and provides solutions that genuinely add value to their business.

It’s only for certain industries or products

Some sales teams assume that cross-selling is only relevant for specific industries or product lines. In reality, every business has the potential to cross-sell complementary products or services that enhance the customer's experience and drive additional revenue.

Contrary to these misconceptions, cross-selling is a crucial strategy for sales teams to maximize customer lifetime value and foster long-term relationships. By offering tailored solutions that address the customer's evolving needs, sales teams can position themselves as trusted advisors, leading to increased customer satisfaction, loyalty, and revenue growth.

What’s the biggest challenge in getting your reps to cross-sell and upsell more effectively, and how can you train them to do it successfully?

The cross sell and upsell challenge

Sales reps often hit some speed bumps when it comes to cross-selling and upselling. Even with all the company’s product knowledge at their fingertips, some deals still end up as one-and-done, leaving a lot of potential revenue just hanging out there, untouched. Why does this happen? Well, it could be anything from not fully knowing the products, to missing out on key discovery moments, or just not having the right strategic playbook in hand.

One of the biggest challenges? Not digging deep enough with prospects! When sales reps miss out on those rich, meaningful discovery conversations, it’s like trying to solve a puzzle with missing pieces. Without truly understanding the customer’s needs, pain points, and long-term goals, spotting those golden cross-selling opportunities becomes a real uphill battle. It’s easy to overlook potential connections or stumble when explaining the added value of extra offerings.

Keeping up with ever-changing product lines and feature updates can feel like trying to catch a train that's always speeding up! If sales teams rely on outdated or incomplete product knowledge, it can hurt their credibility and make it tough to position cross-selling opportunities with confidence.

And let’s be honest—nobody likes feeling lost, especially in the middle of a sales cycle. Without a well-defined sales playbook and actionable guidance, sales reps can feel like they’re navigating a maze without a map. That means they might miss those perfect moments to introduce complementary solutions.

When this happens, companies miss out on maximizing their product portfolio's potential, leaving a ton of revenue on the table. To truly drive sustainable growth and boost customer lifetime value, tackling these cross-selling challenges head-on is key!

Businesses that implement AI-driven cross-selling strategies have experienced a significant increase in their sales by up to 20%
Source: Success.ai

Essential ingredients for cross selling and upselling

To truly master cross-selling and unlock more revenue, sales teams need to shine in three key areas:

  1. Getting to the heart of what customers need: Nailing cross-selling starts with truly understanding what makes your customers tick. It’s all about asking the right questions, really listening to their answers, and uncovering the real reasons behind their decisions. When you know their needs, pain points, and goals inside out, you can offer them exactly what they’re looking for.
  2. Knowing your product’s superpowers: It’s not just about knowing the bells and whistles; it’s about understanding the real magic behind your products. Sales reps need to clearly explain how their solutions tackle the customer’s challenges, bring real benefits, and deliver a fantastic return on investment.
  3. Highlighting what makes your product a rockstar: In a crowded market, standing out is everything. Sales teams need to spotlight what makes their products or services the absolute best choice. Whether it’s unique features, unbeatable advantages, or something that makes your offering truly special, it’s crucial to make sure customers see why your product is the perfect fit for them.

By mastering these 3 areas, sales reps can position themselves in a confident way on calls and increase the no. of cross sells and/or upsells along with the existing product.

How Zime drives cross-sell opportunities
How Zime drives cross-sell opportunities

How to solve this with Behavioral Science and AI

Zime keeps everything organized by capturing your company's tribal knowledge, including past sales calls and customer responses. It then generates a clear action checklist for your reps, ensuring they’re fully prepared for each call. Say goodbye to last-minute scrambling and missed opportunities for cross-selling or upselling.

In-depth discovery to boost cross-selling opportunities

With Zime, your AI-powered sidekick, you can leave the stress of juggling a million details behind, especially during those crucial discovery calls. Zime’s got your back with a handy pre-call action checklist that pops up right in your messaging channel. This nifty feature ensures your reps are fully prepped, knowing all about the client, the product, and exactly where the deal stands. When it comes to discovery calls, they’ll have all the right questions lined up and ready to go. Armed with the latest info, your reps can dive into meaningful conversations, getting to the heart of what the client really needs. This deeper understanding sets them up perfectly to cross-sell and upsell, whether it’s right after the initial purchase or down the road when the timing’s just right.

Sounds like a nightmare, doesn’t it?
Checklist delivered right into your messaging app one hour before the call

From features to benefits: keeping reps updated for stronger pitches

Apart from the features of the product, sales teams must be updated with it’s benefits too so they can convey what it’s like to use this product. How it incorporates the customer’s lifestyle and how it can benefit them. To be able to purchase, customers will see the value and positioning first. This is also where Zime chimes in and does its magic. All the information once created in the sales playbook (that is now shelf-ware) is updated and reps know the latest info on how to talk about the product, its features and benefits.

Product differentiation so your reps can be more confident

In a highly competitive market, there has to be a product that stands out from the rest. Having this info alone can increase sales by the sales reps on the sales calls or proceed further than the discovery call. This also enables cross sell and upsell further because of how different the existing product is and how the customer would highly think of buying something else alongside too or have an upgrade of the existing product. Zime helps with keeping you updated with all of this through your communication channel (Teams, Slack, or Zoom) so that you know exactly what to say, to whom and how.

By providing these just-in-time actions, Zime ensures that sales reps are well-prepared, knowledgeable, and focused during each sales call. This level of preparedness not only enhances the overall customer experience but also increases the likelihood of successful cross-selling and upselling opportunities. And this is not just for yourself or account executives, this is also for the sales manager.

For sales reps/AEs: Zime spots unresolved pain points that can be tackled with cross-selling, guiding you through the process with a handy cross-sell checklist to close those deals.

For sales managers: Zime gives you a clear view of how your team is seizing cross-sell opportunities and how well they're adopting the cross-sell playbook.

For sales leaders: Zime offers insights into how your team is handling cross-sell opportunities, suggests the next best actions to boost performance, and shares customer feedback on how they're enjoying the cross-sell products.

How Bureau increased their average deal size by 30% on the back of improved discovery

Bureau is a no-code, identity decisioning platform that offers businesses the complete range of risk, compliance and ongoing fraud monitoring solutions innovated with AI.

Before working with us, one of the big hurdles Bureau faced was getting their sales team to really embrace sales plays—especially during the discovery stage. Let’s face it, discovery calls are the MVPs of the sales game. It’s where you really get to know your potential clients, and it sets the stage for everything that follows. Nailing this part can:

1. Open doors for cross-selling and upselling.

2. Help you truly understand your clients and build rock-solid relationships.

3. Naturally boost sales because your clients can see the real value in your product.

After partnering with us, Bureau saw a 9% bump in quarterly revenue, all thanks to a sharper focus on discovery. The deeper the discovery, the better your chances for selling, cross-selling, and upselling. It’s all connected!

So, how did we help them pull this off?

Enter: Just-in-Time Actions Checklist

Zime’s Just-in-Time Actions Checklist comes to the rescue with a pre-call checklist that slides right into a rep’s communication channel an hour before their call. This handy info ensures they’re fully prepped—knowing their client inside out, reviewing past call info (if there is any), brushing up on product details, and readying the right questions to ask.

With this level of prep, the reps felt super confident going into discovery calls. They weren’t just there to sell—they were there to really understand their clients on a deeper level. And guess what? Their chances to cross-sell and upsell? Through the roof!

To know more about how we solved other challenges, read here.

"Average deal size increased by 30% on the back of improved discovery."
Kapil Bhagat
Kapil Bhagat
AVP, Sales Strategy at Bureau Inc.

Start your Zime journey with a 21-day pilot

If you’re ready to improve your sales playbook adoption, here’s what your next steps would look like:

Pilot for 21 days - no fees, no training till you see results.

No more shelf-ware playbook or a graveyard of call recordings!

Sounds like a nightmare, doesn’t it?
That's exactly how our customers feel when they use Zime.
Tags: cross sell, upsell, cross sell and upsell, AI sales tool, sales rep, sales leader.
Sanchit Garg
Sanchit Garg
Cofounder & CEO, Zime
Meaningful goals drive me. My goal is to empower everyone to be a top-performer with accurate nudges in the workflow. Before InnerFit, I founded TravelTriangle for "Holiday Experience," which achieved market leadership with $42mn+ ARR and a team size of 700+ go-getters.
In this Blog

Frequently asked questions
What is upsell and cross sell?
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Upselling and cross-selling are sales techniques used to increase the value of a sale:

Upselling: This involves encouraging a customer to purchase a more expensive version of a product or service they’re already considering. For example, if a customer is looking at a basic software package, an upsell would involve offering them a premium version with additional features.

Cross-selling: This entails suggesting complementary products or services to a customer based on what they’re already buying. For instance, if a customer is buying a laptop, a cross-sell would be to recommend accessories like a laptop bag or a wireless mouse.

Both techniques aim to enhance the customer’s overall experience and increase the total revenue from a sale.

How does AI sales coaching help in advancing a deal?
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Reps benefit from cross-selling alongside existing products for several reasons:

1. Increased Revenue: By recommending complementary products, reps can boost the total value of each sale, enhancing overall revenue without needing to acquire new customers.

2. Stronger Customer Relationships: By providing valuable recommendations, reps build trust and demonstrate their understanding of the customer’s needs, fostering long-term relationships.

3. Improved Product Utilization: Customers who use complementary products are more likely to realize the full potential of their initial purchase, which can lead to better outcomes and increased likelihood of future purchases.

4. Competitive Advantage: Offering tailored solutions and additional value can differentiate a company from competitors, helping to retain customers and attract new ones.

How does AI help with cross selling?
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AI enhances upselling and cross-selling by personalizing recommendations based on customer data, analyzing behavior to identify trends, and providing real-time insights during interactions. It automates suggestions, uses predictive modeling to forecast responses, improves customer segmentation for targeted offers, and delivers deeper insights for more strategic sales approaches.

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