Why is Upsell/Cross-Sell Important

Cross-sell and upsell (collectively referred to as “expansion) are vital for CS teams to have a direct impact on net revenue retention. 

Many customer success teams today operate reactively. They fixate on tactical KPIs around onboarding, NPS, usage, support, and customer escalations. While these domains are important as leading indicators for a business’s revenues, they fail to directly impact key financial metrics of the business. 

A better approach for customer success teams is to prioritize retention as a primary driver of revenue. However, even that may fall short of maximizing growth potential. 

The best customer success teams go beyond retention and actively focus on expansion through upsell and cross-sell, aiming to increase the value derived from the existing customer base. Without considering expansion, a customer success team lacks critical impact on their revenue strategy, limiting their ability to achieve optimal customer outcomes and revenue outcomes.

Account expansion also has benefits beyond just increasing revenue:

• Expansion predicts long-term retention – In most businesses, customers who buy more stick around longer.
• Expansion offsets churn  – Expansion in good-fit customers allows teams the freedom to churn other, poorer fit customers, while maintaining strong NRR.
• Expansion supports building a large, robust post-sales team with efficient specializations – Healthy expansion helps justify hiring and maintaining a large, well-staffed and well-specialized team for CS, support, onboarding, and professional services.
• Expansion motivates CSMs, promoting long-term employee retention – Customer success as a field can be highly prone to burnout. CSM well-being is important not only an important goal in and of itself, but also for the finances of a business. The replacement costs on CSMs can be very high. Motivating CSMs with expansion gamifies the CS function in a way that can be quite motivating to a team.

Furthermore, “land and expand” models are among the most successful models today – Selling a dollar of upsell/cross-sell bookings is often much more efficient than selling a dollar of new logo bookings. This strategy can work for both small and large companies going to market with one product and then branching out into other products, creating a sustainable business in the long term.

What are common obstacles companies face when approaching expansion efforts? 

There’s a limited customer base to sell into – Given that CSMs are selling to a very limited addressable market, smaller, younger companies may quickly exhaust their pool of existing customers to upsell or cross-sell. This is especially true in early stage companies and enterprise B2B environments, where there are fewer logos to sell.

It risks burning existing customer relationships – Aggressively pushing for upsells or expansions may strain existing customer relationships, leading to negative revenue results in the form of increased churn. Correct, delicate messaging is essential to frame expansion to the customer’s benefit.

Insufficient skills and opportunities for practice among CS teams – Customer Success teams often lack dedicated resources and sales training from leadership, making it difficult for them to effectively sell new products or services. Effective expansion starts at the top.

Insufficient customer success bandwidth – Because they’re dealing with such a wide array of KPIs, CSMs often lack the time to rehearse and refine their sales skills. Adding more responsibilities to CS teams can lead to burnout, especially if these teams have already been reduced due to economic factors.

Building a Program

What are the phases of building an account expansion motion? 

Phase 1: Making the Case to Leadership – CS leaders should begin with a thoughtful, honest, and calculated reflection as to whether they are truly the best-equipped to own expansion. While there are clear reasons in favor of CS, the reasons listed above often impede building a scalable function. Sales may also make a compelling case to own expansion (which also comes with its own set of pros and cons – CS teams often report that Sales is more likely to hurt client relationships or conflict with CS initiatives).

If CS is the best fit, CS leaders should present a well-thought-out case to align with the broader leadership team, including C-level executives, to gain their support for CS ownership. This alignment is critical. If the leadership team is not on-board, expansion often fails. In making this case, CS leaders should use a quantitative, scientific approach to size the market and quantify conversion rates to optimal revenue outcomes. 

If CSMs are tied down with other obligations, consider creating a new “Commercial CSM” role in CS that’s entirely focused on revenue outcomes.

Phase 2: Preparing your CS team to sell – As a CS leader, training your Customer Success Managers (CSMs) to be effective salespeople is essential. While many CSMs haven’t had as many opportunities to handle sales, effective training can teach them how to handle objections and close deals. This phase involves iterating on your pitch and ensuring CSMs are comfortable and diligent in negotiating commercial terms with customers.

Phase 3: Scaling Your Team – Incorporating sales into every facet of the customer interaction can take your expansion efforts to the next level. Starting with onboarding, introduce customers to the full ecosystem of products you offer from the start. In support, train support reps to keep an open eye for other ways your company can help its customers with the addition of more products. Finally, revisit staffing and hiring career AEs with years of experience who can help drive the closing process. While most CSMs haven’t held high quota-bearing roles, AEs have this experience in spades.

Phase 4: Iteration and Scale – At scale, managing expansion involves learning how to work with sales data, manage pipelines, and improve the customer journey in a scalable fashion. Continuously refine your approach to ensure ongoing success and growth. 

As a rule of thumb, managers should regularly run themselves through the process of being sold on upsells and cross-sells and ask themselves: “If I were a customer, would I enjoy this experience?”

What does the CS leader owning account expansion need to do before launching the program? 

Learn to speak fluently in the language and metrics of sales – Before building an expansion program, it’s crucial for leaders to be able to speak the language of sales. Many young CS leaders have to learn not just the concepts of sales efficiency, customer acquisition costs, LTV to CAC ratios, and payback period, but be able to model them analytically as well.

Build efficient expansion playbooks – Understanding sales workflows and being able to build automated sales cadences is essential. This involves tracking metrics like dials and sets, knowing how to segment the market, prioritizing between segments, and tracking conversion rates through different parts of the sales funnel.

Have conversations with Sales and the C-Suite – When CS owns expansion, proactively engaging in regular conversations with sales and C-Suite members is vital to maintain executive alignment. This helps in understanding their perspectives, collaborating over common sales collateral and documentation, and aligning your expansion program with the company’s goals and objectives.

Earn your position to sell by doing it yourself – As a CS leader looking to own expansion, you must win the trust of your team by doing initial sales yourself – and proving it works. This means putting yourself out in front of prospects and demonstrating your skills in closing deals before hiring and scaling a team. Without this track record, it’s difficult to gain internal alignment around your ownership of expansion.

Upsell opportunity sizing – Size the customer base, identify opportunities, and analyze market segments to build a successful expansion program. This involves understanding the market landscape and prioritizing segments based on their potential for growth and profitability.

Who should own account expansion at scale? Introducing the role of the Commercial CSM

While CS and Sales teams often debate about ownership of expansion, having a commercial function within the CS team is generally the optimal model – Many companies disagree on who is best to own upsell and cross-sell, pitting sales versus CS as the two options. In reality, the choice may be less binary. An ideal hybrid is often a commercial CSM – a CSM who knows how to sell, but sits within the CS team. 

The reason this model is effective is two-fold:

First, selling to existing customers requires correct timing and collaboration with CS – a surefire way to ruin a deal is when a customer is hit with conflicting initiatives. For instance, if a CSM is working a renewal and a sales AE swoops in for an upsell, customers may not only have a poor experience, but may also leverage different company initiatives against each other. Unlike sales AEs, commercial CSMs will be in all the meetings with CS, developing rapport and coordination within the team, and reducing the odds of interdepartmental miscommunication and friction.

Second, expansion selling requires a deep understanding of customers, and sitting within the customer success organization develops unmatched customer empathy – unlike sales AEs, commercial CSMs monitor customers closely and build ongoing rapport throughout the customer journey. They learn to pitch their product in a way that’s congruent with CS verbiage and in sync with CS initiatives, resulting in a seamless experience for the customer. This model also reduces the chance of oversell. Because the commercial CSM resides in the CS team, they are responsible for ensuring delivery on customer promises.

Very small companies may have to choose for CS or sales own account expansion – These are suboptimal models, but in the beginning, you might not have the resources to have separate commercial CSM.It’s fine to have sales or CSM own account expansion at first, but most companies will outgrow this model very quickly. 

Other hybrid models where CS and sales share responsibility aren’t generally recommended – The below models often get too messy for the customer and company to be operable.

How do you set Commercial CSMs up for success?

A salesperson within your CSM function can be either a seasoned AE trained on CS or a CSM trained on sales. Finding a hire with Sales and CSM experience can be rare, but it’s certainly not impossible. If there is a CSM on your team with sales interest or experience, you can train them to prepare them for the specifics of the role. Alternatively, you can hire an experienced salesperson and train them on the nuances of being a CSM.

Tip: Teaching CS to Sales is often easier than teaching Sales to CS – Because sales workflows are often more routine and driven toward a single revenue KPI, it’s often easier to train CS on Sales than Sales on CS. That said, CS often needs ample coaching and guidance.

CS needs the right tooling to succeed – Successful commercial CSMs need the different software tools that support your typical sales processes—there are a lot of automation tools like Salesloft, Outreach.io, etc.

Provide Commercial CSMs with the right comp structures – Commercial CSMs should have their financial outcomes aligned with those of the business. A commercial CSM should be compensated not like a CSM, but like a traditional salesperson—often with half their compensation composed of variable commission and with on-target earnings that exceed that of a typical CSM. 

Expansion Selling Best Practices

What kind of sales practices can help your CS organization conduct cross-sells and upsells? 

Prepare CSMs mentally to sell – A lot of CSMs don’t identify as salespeople and have to purposefully adopt a sales mindset to set demos or close deals. But ironically, the most successful salespeople are often the ones that don’t identify as salespeople. For instance, it’s often a hurdle for CSMs to get over a fear of rejection, but leaders can ask CSMs to remind themselves: “What’s the worst thing that could happen on this call?” CSMs may fare better if they don’t “try” to sell, but rather adopt an approach that disclaims to the customer that it’s part of their job to ensure customers are at least aware of all product lines you offer as a company.

Build talk tracks with this disclaimer – CSMs ought to create and rehearse a comfortable talk track to explain the context of their sale from a CS perspective to customers. This talk track might look something like:

 “I’m not on the sales team; I’m on customer success. What that means is that my responsibility is making sure you adopt and see value from all parts of our product across all lines of business. So part of my job is walking you through all the products and pricing plans in our catalog and determining if they’re a good fit. 

If not, no worries. If all I leave this conversation with is your feedback, I consider that a win. That said, I really think there’s a potential fit here for you to buy and use our additional products.” 

Prepare for selling by practicing with low-stress situations – If you’re in customer success, try the talk track on customers where you have little to lose. That might be customers who you have such a good bond with that they’re not going anywhere, such as the customers on your customer advisory board. Or it may even be customers on the other end of the spectrum who are already disqualified, so you have nothing to lose. You might also practice on low-dollar-value customers, or with gatekeepers who aren’t actual decision makers. Regardless, it’s important for CSMs to get their reps in before approaching economic buyers.

Learn how to earn a seat at the table with the economic buyer – Often, economic buyers are top officers who have very little time on their hands to sit through demos. They may have 30 different providers, and you can be confident that they’re not spending 30 hours a month having meetings with all their different vendors. As an effective seller, you have to become important to them by identifying the pain they experience and its urgency. Effective commercial CSMs should make clear to the economic buyer that it’s not just a matter of why the VITO should sign up for this expansion, but why now.

Developing customer research skills – One area where CS often has an advantage over sales in expansion is conducting deep customer research. CS has access to a ton of customer data at their fingertips and are learning a lot about their customer industries as well. The research about a customer’s product usage or their industry can give a lot of ground to earn a seat at the table with the economic buyer.

Maintain a 50/50 talk time with the customer when selling – Many deals go sour when a salesperson goes into “telling mode,” not asking the customer about their use case and deepening understanding of their “why.” To this end, there’s been a lot of research done about talk time – the ratio of time your team is talking versus your customer is talking. A 50/50 balance is a good bar to aim for, where your team is speaking at most half the time in the conversation. 

This can often be achieved when commercial CSMs adopt a socratic, question-oriented approach to sales, where they get the customer talking more than they are. Aspirationally, CSMs ought to remember the advice that “You have two ears and one mouth, and you should use them in that proportion.” 

Many often also have to learn when to stop talking when they get the answer they want. In the words of some experienced salespeople, “When you get the answer you want, shut up!”

To sell effectively, CS often needs to learn to sell value, not features – One of the most common mistakes that inexperienced CS employees make is to sell features and functionality – the “F words” – rather than selling value after deep discovery of pain points. Effective CS salespeople uncover the customer’s “why” and understand the journey that brought them to this point. Only then do they show how you provide value and can alleviate their pain. Ironically, some of the most effective sales barely even demonstrate the product. The formula for a pitch starts with pain discovery. 

When should you approach current customers about expansion? How can you approach upselling and cross-selling as early as customer onboarding?

You actually have a better chance of upselling and cross-selling during onboarding – Many companies hesitate to talk about expansion during onboarding given the novelty of the relationship. However, in onboarding, you actually have a natural and controlled rationale for introducing new products to the customer. You can say that a core responsibility of the onboarding process is to demonstrate the whole ecosystem of products you have, since your most successful customers are at least aware of all you offer. Educating customers on your full offering is just part of what you do to create educated successful customers.

This can be similar to the experience of getting your oil changed at a professional mechanic shop. When you bring your car in, the most effective mechanics educate you as the consumer about risks to your car, purely as a matter of client education. You as a customer don’t mind and don’t feel like you’re being sold to. If an upsell happens as a result of this education, that’s great! If not, there’s no hard feelings.

Selling becomes more nuanced post-onboarding – The customer lifecycle post-onboarding becomes far less structured and more like the wild west. As a seller, you no longer have a captive audience and customers may feel less urgency to expand. While CSMs should still broach account expansion during QBRs or during renewals, the onboarding process is a way to sell early and consistently.

Take an honest look at your customer journey – It’s important to role play the customer journey with yourself as the customer and ask if you would enjoy the experience you have created. Look at where you broach upsells/cross-sells and consider whether that’s the right timing.

What kind of objections can you expect from current customers? How should you counter these?

Some of the most common objections include:  

• I have to get approval 
• I need to think on this
• I don’t have budget
• I don’t have time 

Get ahead of objections during your onboarding process – Prevent yourself from being thwarted by unforeseen obstacles by asking how decisions get made as an organization during your kickoff process. Ask the customer from the jump: “What is your internal approval process when it comes to renewals and expansions?” This should be an important required question in onboarding because it gives you foresight into what you’ll deal with down the road. Selling without this information is like not studying film as an athlete. You’re not setting yourself up for success.

Use the “Feel, Felt, Found” approach to difficult conversations – This is a simple methodology to navigate customer objections. When a customer says something you disagree with, you’ll be inclined to argue why it’s not true. Even if you’re nice about it, it can sound like you’re debating them and that’s not the beginning of a successful outcome. 

When you feel the need to rebut, instead use this framework: 

• Feel – Prove that you feel what the customer is feeling. This wins customer trust. While this may feel counterintuitive, sellers should lean hard into this, mirroring customer verbiage and going as far as to elaborate on what the customer feels. This shows the customer you empathize them and earns their trust.
• Felt – Inform customers that you have dealt with people who have felt this way before. This shows your experience as a trusted industry advisor.
• Found – Share success stories and statistics that support your finding/point of view.

How do you manage the pipeline of cross-sell and upsell opportunities? How is it different from managing your pipeline of new opportunities? 

The main difference is that every relationship is very precious – Because of how limited the total addressable market is for expansion (considering that it’s just your current customers), every relationship and touchpoint is important to maximize. 

Start CS meetings by talking about lost deals – Developing a sales culture can be tricky. Sales teams often get the reputation of being overly confident and macho. As a result, many sales pipeline meetings get lost in fantasy projections of deals that will close. When building a sales culture within CS, what can be more effective is flipping that culture on its head and starting meetings with reps talking about what deals were lost that week, and create a blameless post-mortem atmosphere. You’re all there to support each other.

Managers ought to maintain an open dialogue about the scope and bandwidth of the CSM job – If you don’t have a commercial CSM, and regular CSMs work on sales, they’re probably also responsible for NPS, usage monitoring, onboarding, support, etc. It’s important to have an open dialogue about the tradeoffs you may be asking CSMs to make when diverting their attention to sales.

What are the most important pieces to get right?

Hiring the right people – if you’re going to ask CSMs to sell, you need to have talented CSMS that can handle the upsell and cross-sell conversations—particularly if they’re also going to handle customer success activities.

Having the right interdepartmental relationships – you need to be able to build alliances with your sales team, your marketing team, and your product teams so that you’re not stepping on each other’s toes and getting angry with each other during the account expansion motion. 

Having the right tooling – Building in the right automation is crucial to keep your team efficient and organized. Commercial CSMs need to have the tooling to succeed. Ensure you get this buy-in from leadership, as sales tools are often quite an investment.