Customer success playbook

Customer Success Playbook: A Guide to Upselling & Cross-selling

The customer is always right, or so the phrase goes. But what’s interesting is the more you begin to play by the customer success playbook and reward your customer, the more they begin to think you are always right. It’s called brand loyalty. When the time comes for up-selling and cross-selling, loyal customers will be the first onboard.

By having a customer success playbook, your sales team can learn important sales skills and master the art of understanding customers.

When you focus on the hardened principles of customer success, you can get a much better gauge of your customer, their needs, and how to engage with them effectively. As customer success rapidly evolves, it’s important to keep up with the times and market trends. This article is your customer success playbook; let’s dive into the most essential methods to upsell and cross-sell effectively.

Firstly, let’s cut the jargon…

Table of Contents

Understanding the Terminology

A customer success playbook is already a bit of a mouthful, but what about upselling and cross-selling? What are we even talking about?

What is Upselling?

Upselling is the practice of trying to convince your prospect to upgrade their purchase to unlock more features. Upselling is designed to increase the value of a single purchase.

Companies with successful upselling strategies can experience a 75% increase in customer retention rates according to Gartner.

What is Cross-Selling?

Cross-selling, however, is the process of trying to sell additional items that are related to the current purchase they are making. Cross-selling can increase the lifetime value of a customer by up to 14%.

Both upselling and cross-selling are easily achieved when you empathize and relate on a human level with the prospect. So how do you do that?

Understanding Customer Needs

In any industry, understanding and knowing your customers’ needs is integral to success. Excellent customer service is something that all businesses should be striving for. Whatever sells the most sounds like the best strategy, but if you’re competing against numerous competitors, you need to stand out from the crowd.

Customer-centric companies are 60% more successful than those that don’t put a large amount of focus on the customer. If you can relate and empathize on a deep level, that will translate into sales. 

To achieve this, you need to figure out your customers’ pain points and understand their customer journey, right from when they first signed up. Then work with your customer in an effort to help them achieve their goals.

If you want some more guidance for getting a deeper understanding of your customer, check out our 14 customer-centric principles,

So which pain points are common with customers?

Customer Pain Points

Customer pain points are specific problems that your customer is having with your company or the service your company is providing. It’s usually thought of as a hurdle or something that causes irritation for the user, which may result in them ceasing to use your service in the future if left unchecked.

Pain points can be common among many or they can be highly specific to the individual. At the end of the day, every customer is different and so are their pain points. It’s your job to find out what they are, and remedy them.

“Your most unhappy customers are your greatest source of learning.”

When looking into customer pain points, the customer you are conversing with might not even realize they are struggling with another service or product. By asking open-ended questions and encouraging honesty, you can guide the customer to a realization that you could be the answer to their woes. 

Remember, you’re not forcing your product to be the solution to all pain points. You’re purposely prospecting people with pain points that your product alleviates. 

Let’s take a look at three specific pain points.

1. Support Pain Points

If your prospects or customers have a pain point relating to support, it means they haven’t been receiving the service or assistance needed during their customer lifecycle and general sales experience.

Make sure you have a customer support team in place to ensure a smooth customer lifecycle. A customer success team should also dedicate their energy to improving the lives of their customers as much as they possibly can. This means being open to criticism and listening to potential concerns with empathy.

Use power words that are inclusive like “We” and “Us” as it makes your potential customers feel like you are there for them. You’re in it together and you understand their problem just as much as they do. You’re not trying to sell them something, you’re trying to solve their problem. 

2. Financial Pain Points

If financial pain points arrive, it’s usually because your prospect is not getting enough value out of their current deal. It’s a common issue, and you’re likely to encounter it from time to time.

While offering deals and lowering your prices temporarily can be a good way to snag more customers, it’s not something that should become a go-to. You choose your price for a number of reasons. Ultimately, you should know the lowest possible offer that your sales reps will offer.

Having said that, a short-term loss can be a long-term gain. Assist your prospect by assuring them of the savings they can make with your company and back it up with figures to show how much they could save transferring over to you. If you come prepared like this with a full presentation, perhaps during one of the follow-up calls, you can be sure it’s going to attract attention.

3. Productivity Pain Points

If your prospect feels their precious time is being wasted, they’ll be quick to jump ship. 

Factors such as internal communication and complex operating systems contribute to these pain points in particular. Something that should be a run-of-the-mill process could take way longer if there’s a lack of organization. This is something to always remain vigilant of.

Virtually demonstrate any complex systems to flatten out any steep learning curves. Show the amount of time you saved due to efficient and effective software. You can also gather testimonials and feedback from existing customers to present success stories that the prospect can relate to. 

When it comes to up-selling and cross-selling, this is arguably even easier. The customer will already have first-hand experience with your product and they’re automatically more likely to listen to what you have to say. 

Customer Persona Development

Another step in understanding customer needs is developing a customer persona. You need to know who your target audience is before you start trying to sell to any Tom, Dick, and Harry.

All customers are different. Building customer personas prepares you to deal with a wide variety of different people, and still find a core nugget they have in common: they are looking for a solution to their problem. Your brand is the solution. 

When used correctly, customer personas can guide you to the best way to approach up-selling. It allows you to tailor your service to specific demographics.

Customer personas can be developed in four easy-to-follow steps:

  1. Collect and research customer data. Understand what drives prospects: their goals but also their pain points.
  2. Segment your customer portfolio. Split your customer portfolio into sections based on similarities and shared characteristics. The groups can be based on factors such as the demographics of your prospect, behavior, or their values/interests.
  3. Create detailed sales profiles. Manufacture detailed sales profiles and customer personas using the following information: 
    • Demographics: Gender, age, location, education, job, income…
    • Goals. What are they trying to achieve?
    • Values. What are their core values? What do they firmly believe in? Think also in terms of interests and hobbies.
    • Behavioral traits. How does the customer act in regards to their sales lifecycle? Do they have preferences with software and media, or do they have specific buying patterns?
    • Pain points. What grinds your prospect’s gears? Discover what stands in between your prospect and their goal.
    • Customers’ lifecycle and strategy. Create different personas that have unique customer journeys. What would customer success look like to them?
  4. Integration. Integrate your customer personas into the relevant processes, optimizing different buyer journeys and experiences.

For further reference, below is an example of a customer development persona.

Customer Persona Profile

Name: Michelle

Demographics: Female, 35, urban, high earner.

Behavioral Traits: Loves to try out new technology. She’s passionate about streamlining her workload and earning herself some more free time. She’s an avid hiker.

Goals: She wants to save herself an extra 5 hours per week that she will use for her hobbies and downtime.

Pain Points: Hates ineffective communication. She’s always looking at increasing efficiency as time is valuable to her.

Customer Lifecycle: She values companies that make an effort to keep her in the loop and those that offer services that will save her time.

Timing Is Everything

We’ve all heard about The Tortoise and the Hare; it’s not always the quickest that wins the race. That’s why the timing of an approach to up-sell and cross-sell is essential. Don’t jump the gun once you have that initial commitment. Sometimes it’s better to slow down and take your time. Of course, it all depends on the customer, and with your in-depth customer research, you’ll know what will work best on a person-to-person basis. 

Building trust and offering as much support as possible can be the difference between gaining a sale and losing a deal. Again, the timing is everything; too much information in relation to a product you’re trying to up-sell can be overwhelming and cause your prospect to disengage. Waiting too long, however, could also be a hindrance as your prospect could get impatient and look elsewhere.

“Either you run the day or the day runs you.”

Touch points, when broken down simply, are interactions between customers and businesses during the customer lifecycle. By prioritizing customer touch points and maximizing their potential, you’ll improve your customer experience and leave them ready to come back for more.

Touch points are mapped out to exemplify how the average customer journey looks and when it would be appropriate to suggest up-selling and cross-selling.

5 Key Touchpoints

Touchpoints can happen at many different stages of the customer’s journey. From the moment they first hear about your brand to the time they consider it and actually decide to use it, all the way to when they double down their desires and continue to use your product or service, or even advocate for others to use it.

If you’re looking to upsell or cross-sell, you’re in stages 3 or 4. Our five touchpoints will be focused on the “decision” and “retention” stages of the customer journey.

Customer touchpoints for your success journey.

Here are five examples of key touchpoints.

1. Starting a Subscription

Once your customer makes their first purchase with you, the rapport is already built and they are already engaged. It’s a prime time to upsell. Prospects are likely happier to explore other services and products that you provide during this touch point.

2. Onboarding

When your customers are in the process of learning how to use your product, there is an opportunity to offer additional services that could upgrade their experience. This can get intrusive quickly, so be careful not to overuse it here. You don’t want to appear like you’re gatekeeping certain features of your product as soon as the customer has started paying.

3. Follow-Up

After the purchase of your product or subscription has been completed, a routine email follow-up or phone call could be an opportune time to suggest further services to aid their needs.

4. Customer Support

If your clients reach out for help or support, it may be appropriate to suggest additional services to address their problems. Use this with caution. A general rule of thumb is that if you can solve it without up-selling, then offer the free solution first and foremost.

5. Subscription Management

If your business has a subscription model, whenever a renewal is due, approach customers and offer them upgrades to their current plan. It’s an effective touch point to initiate up-selling dialogue.

When you plan accordingly and use each touch point to the best of its ability, you can capitalize on up-selling opportunities and increase customer satisfaction.

Leverage Customer Signals

Judging your prospect’s intent can be difficult when assessing upselling opportunities. But by understanding common buying signals, you can gauge whether your prospect or customer is ready to actually go ahead with the purchase of the subscription or software.

You should delve deeper into the intentions behind buying signals by assessing and interpreting each customer differently. Active listening is essential. You can understand cues verbally that indicate the prospect or customer’s intentions to move the conversation or process forward. Let the prospect do the talking and they’ll often help you out.

As mentioned before, open-ended questions are a great way to encourage your prospect or customer to be more specific and explain in detail what they’re seeking from this business relationship.

It’s essential to pay attention to the feedback provided during interactions. Buying signals can be indicated through customer surveys, interviews, or reviews, all of which could give you ample opportunity to upsell.

Furthermore, analyzing your customer engagement such as response rates, click-through rates, and whether marketing emails have been opened, can give you an idea about whether specific marketing campaigns are having their desired effects or if you need to change your strategy. If they are disengaged, the chances of upselling are increasingly slim.

Check this article for ways to boost your sales performance metrics.

Personalizing Your Approach

Personalized marketing campaigns help businesses to aim for a particular demographic and propose upselling and cross-selling opportunities. If your customer feels like you’re specifically focused on them, they’ll be more open to ideas and upgrades. 

Below you can delve deeper into the benefits of personalizing recommendations.

Customer Satisfaction

When you personally tailor your sales approach to an individual customer or business, they’re going to feel like you actually give a sh*t. This enhances customer satisfaction and instills loyalty. A loyal customer means more money spent on your product.

Increased Revenue and Conversions

Personalized recommendations targeted to the right people at the right time can increase your conversion rate and revenue. If customers receive promotions that are tailor-made to their needs, they’re more likely to be influenced to make additional purchases and upgrades.

Customer Retention

Match the right marketing campaign to the right individual and you will build a much stronger relationship with your customers. When the connection is there, customers don’t feel the need to jump ship on every wave. They are here for the long-haul.

Data and Insights

Collect customer data to optimize strategies and campaigns. You can do this by analyzing the data to get a more comprehensive view of the customer’s wants, needs, and pain points. 

If you want a good place to start, check out a customer’s browsing behavior, demographics, and purchase history. 

1. Demographics

For a retailer in clothing, you can segment your audience into male and female, personalizing emails to provide a look into your brand’s new range.

2. Browsing Behavior

If your customer has been looking at going on a spa weekend and browsing through the different packages on your website, you can personalize your recommendations by sending offers and exclusive deals to them with discounts.

3. Purchase History

Do you have a customer that’s previously made a subscription to your basic plan for your software? Suggest an upgrade to a premium plan, with extra features and integrations to enhance their experience.

“Don’t find customers for your products, find products for your customers.”

Educating Customers on Value

In a customer success playbook, you need to understand what value your proposition has for your customer. They will have an abundance of choices, fighting it out to secure their subscription or purchase. What makes your product/company special?

Helping your customers understand the benefits of what your service provides compared to your competitors will make their life easier. You have to clearly articulate the values of your service, not just with short snappy sentences, but with cold hard facts. Talking the talk is no good unless you can also walk the walk.

Get it into the mind of all your sales reps: an educated customer is a valuable customer. When a customer fully understands the value of your upsells, it’s critical to your business health, not just a singular sales pitch. It’s the victory in a single battle that contributes towards the victory of the entire war. 

To emphasize: it’s not just a before-sale job, educating your customers should be a continuous strategy. Knowledge is wealth. The more knowledge your customer has in relation to why they should upgrade, the more inclined they will be to go ahead with your suggestions.

There’s a variety of tricks you can pull from your customer success playbook. Here are some of them.

Use infographics or Visuals

Visual information is processed a lot quicker by the brain. People remember visuals more too. It’s a quick, easy way to drill your value proposition into the customer’s skull.

Social Media and Channels

The internet is full to the brim of different communication channels that can share information in various formats. Find out which corner of the internet your customers hang out in. Be present there. By providing engaging content for relevant platforms, you can convey your message directly to the hearts of your future customer.

Clear and Concise Communication

Ensure your communication is easy to understand. Be clear and concise. Express the value of your product as clearly as possible. How does it benefit the user?

Tailor-Made Messaging

Create messages that are tailor-made to each customer’s specific requirements based on previous sales history and future intentions. A personal and direct approach will amplify your customers’ experience with your company.

Training and Onboarding Workshops

Provide your customers with the information and tools needed to succeed with your product. Give them tutorials, walkthroughs, and quality customer support when they need it. This ensures your customers get the best bang for their buck. 

It’s your job to make the onboarding experience as seamless as possible. You can use tl;dv for this exact reason, getting all your employees on the same page of your customer success playbook near-instantly. Just record your meetings and merge them into bite-sized clips and reels to demonstrate real-life examples.

Overcoming Objections

Confidence. If you’re confident in your knowledge of the product then you’re already on to a winner. With the opportunity to offer solutions to customer pain points through upselling, you should pre-emptively prepare for objections. They are inevitable and successful sales teams take them in their stride rather than view them as setbacks.

Once again, active listening is essential when dealing with objections. One of the most important but underrated skills to ensure maximum customer success is just shutting up and listening. When you listen, empathize, and understand the objection, rather than immediately dismiss it, the customer will trust you more and your relationship will grow stronger. 

You may need to use statistics to address the objection. This can be done preemptively by including graphs, charts, and other visually-pleasing statistics in the sales pitch itself. You can always keep more detailed stats on hand for when objections are brought forward.

Once you have listened and emphasized, your next step is to address the objections.

Every objection is different. Some are related to a lack of understanding of the product. Sometimes the timing is off. Other times, it might just be a tad too pricey. Let’s take a look at these specific objections and how to deal with them in your pitches.

Lack of Understanding

When a prospect fails to understand your product, you haven’t explained it well enough.

Offer free guidance, videos, infographics, demos, and more to help guide your customer. Be clear and concise with your explanations. Don’t use too much jargon and don’t ramble. Remember, let the prospect do most of the talking. 


It’s not hard to understand or empathize with the customers’ concern that it might not be the right time. However, ensure you follow-up at pre-arranged times to keep the lead warm. Be ready to offer further assistance down the line when they are ready to take the next step.

On the other hand, you could induce FOMO by making time-sensitive offers. It’s possible to twist a prospect’s arm into taking the plunge when this is their only objection, but you don’t want to come across too pushy.


If your customer objects to your pricing structure, you can offer more flexible payments or perhaps a discount to make the purchase more affordable.

However, if you feel like your prospect is trying to pull a fast one on you and you’re confident that your pricing is reasonable, highlight the return on investment that your service offers. Pull up statistics and testimonials to back up your statement. You may even want to reveal a competitor analysis if your pricing is in line with the market.

Start Using Your Customer Success Playbook 

Upselling and cross-selling effectively is not just about using your everyday sales jargon and charming your way to a sale. You have to understand the timing, how to personalize your sales approach, and how to accurately educate your customers on your value proposition.

If you stick to the principles of this customer success playbook, you can provide your team with a 101 into customer success.

It’s not about forcing upgrades down your customer’s throats at any given opportunity, it’s about a perfect amalgamation of timing and execution. With enough practice, you can master the arts of upselling and cross-selling and take your business to the next level.

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