Sep 16, 2021

Read Time 4 min

Getting Customer Success Comfortable with Sales Conversations


When asked to sell to customers, Customer Success Managers (CSMs) are often scared of coming off as too pushy or getting a “no.” There’s a common (albeit misplaced) fear among CSMs that sales talk will tarnish their customer’s trust and set fire to the relationships they’ve worked so hard to build.  

But nothing could be further from the truth so long as you handle your sales conversations with tact, understanding, and integrity.  

As the world’s most well-known salesperson Zig Ziglar once said “If you believe your product or service can fulfill a true need, it’s your moral obligation to sell it.” 

If your customer can benefit from a product upgrade or feature upsell, then it’s your duty to make your customer aware of the opportunity. You do your customer a disservice by using your fear of selling as an excuse to not present them with solutions that would benefit them. 

When you practice honest selling, you have nothing to fear. If a customer tells you “no,” then it’s because the circumstance isn’t right – not because they feel suspect of your motivations. 

Once you adopt this mindset, selling simply becomes a matter of practice.  

Of course, it’s easy to claim you’re not good at something if you never practice, but that doesn’t mean you’re not capable. For many CSMs, selling and negotiating are new skills. As with learning anything new, you need to spend a little time getting comfortable with being uncomfortable, at least initially. All progress takes place outside of your comfort zone; and practice is how you progress.  

Many of the skills that make Customer Success professionals successful – relationship building, problem solving, empathizing – are also what make a great salesperson. The core abilities are there, you just need to reframe them in a new context.   

So, before you write yourself off as a “not good at sales” person, read this advice from Sales and Customer Success leaders on how to make Customer Success professionals comfortable – or dare we say confident – with selling.  

Have Good Intentions When Selling

There’s no way around this one. If you sell from a place of dishonesty or indifference, your customers will know. As Bryan Neale, Founder of Blind Zebra, said in our webinar on selling for people who don’t love sales: “If you don’t want to come off as pushy, if you don’t love selling, you need to carry really strong intentions to be helpful to others.” 

To give an example, Bryan outlined the hypothetical scenario of a CSM whose customer accounts for one division of a company that’s comprised of three divisions. If your product makes a huge impact on that one division’s savings or productivity, then you have an obligation to introduce your product to the other divisions because your intention (to increase the efficiency and cost savings of your customer’s company) is pure. But if you solely act out of a desire to make your bonus or commission, then you’re out of integrity with your intentions. Your mindset always matters. 


Set the Context to Begin Sales Conversations  

During the webinar, Bryan also shared how to use a language framework to approach sales conversations. To feel comfortable setting up a sales call, you need to set the context by creating a statement of intention and giving the customer space. 

To give an example using this framework, Bryan says you could begin the conversation by telling the customer you want to talk to them about something you don’t typically discuss. You state you’ve been watching what’s been happening at the customer’s company and you see a few opportunities where you believe your product could help. You acknowledge that you know the customer hasn’t raised this as a need, but that you’re acting from a place of wanting to help. You tell the customer you want to share your ideas with them, get their feedback, and then they can decide if/when to move forward. 

In this scenario, you’ve stated your intentions out loud (you’ve identified areas for improvement to optimize the customer’s performance), which allows you to enter the sales conversation with space and safety. After you present your ideas, you must give the customer space to either say, “Yes, I’m interested. Let’s keep talking,” “Maybe, let me think about it,” or “No, thanks.” Because you’ve kept your intentions clean, whatever answer your customer gives is OK. You’ve stayed honest and done all that you can do.  


Involve Your Sales Team in Training  

Teaching CSMs to be comfortable with selling can be a challenge, especially for Customer Success professionals who are early on in their careers and might not have many customer-facing interactions or negotiations under their belt.  

As Jason Noble, Global VP of Customer Success at Vinli shared during one of our recent virtual RYG meetups: “Make sure that you’re giving your team guidance and support around commercial negotiations. What I’ve seen happen successfully multiple times is getting your Sales team involved. Get your Sales team to do coaching/training. Sit in on sales calls. Understand who your customers are, how you’re selling, and what that proposition is. Understand the blockers that your Sales team [encounters]. That can really help instill that confidence in your Customer Success team to start having those more commercial conversations.” 

With busy schedules, it can be hard to coordinate a time between teams to sit in on calls. But using a tool like (a conversation intelligence platform), you can record and share important snippets of customer conversations across teams – allowing people to listen to calls at a time that’s conducive to them. 

Bryan also shares a simple yet effective exercise that requires no software, only a smartphone: “There’s no better tool, in my opinion, to prepare you as a CS person for a sales-oriented call that you might be uncomfortable with, than to practice into your phone [using Voice Memos] and listen back to yourself.”  


Customer Success Is in the Business of Selling 

If you’ve done Customer Success right, sales or expansion conversations should be a natural extension of your customer relationship. When you’re selling to solve a legitimate customer need, it shouldn’t feel contrived or disingenuous. The more comfortable you become with selling, the better you can serve your customers.  

“Customer Success involves sales, whether we want to call it sales or not,” says Jason. “We’re there to drive value and outcomes. There’s inevitably a monetary component to the value that our customers are getting from us as Customer Success professionals and leaders […] Once you accept that Customer Success is commercial, the conversations about cross-sells and upsells become a lot easier.” 

And if you still think you’re not in sales if you work in Customer Success – or any field – Zig Ziglar would disagree: “Maybe you don’t hold the title of salesperson, but if the business you are in requires you to deal with people, you my friend, are in sales.” 


Additional resources: 
  • Should CSMs earn sales commissions? Do you need to hire CSMs with sales experience? To hear the thoughts from CS leaders on these matters, listen to our on-demand virtual RYG 
  • Want to make sure your customers never ghost you again during sales conversations, or any conversation? Check out our webinar on selling for people who don’t love sales. 
  • Should Customer Success own the renewal and/or upsell? Hear arguments from both sides of the aisle in our great SaaS debate. 

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Fighting Churn is a newsletter of inspiration, ideas and news on customer success, churn, renewal and other stuff and is curated by ChurnZero



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