This article was transcribed from a presentation given at our virtual Customer Success Festival in October 2022.


Hey, my name is Mark and I’m the Chief Customer Officer Roster. I’m going to talk you through some methodologies and best practices to help you make sales skills part of the customer success toolkit.

I’m going to help you make sure that everyone in your organization is communicating the same way, so you can establish the real uses and capabilities of your product and create greater success.

Without further ado, shall we?

Three fun things to remember

Before we get into how you can integrate sales skills into your toolkit, I’m going to go over some key principles that I want you to keep in mind.

Perfect the journey (there can only be one!)

We need to make sure there is one, unified customer journey. Marketing, business development, sales, implementation, customer success, customer service, and technical support all need to be part of the same journey, the same message, and the same story.

Sales and customer success need to be unified

Whatever sales are trying to establish when they’re selling, we need to back that up as Customer Success Managers. We need to make sure that we are exposing any new goals that customers have and making sure that throughout every step of the journey, customers see where they are in relation to the goal they established when they first came to us.

Sales skills are universal and essential

Sales does the same things that customer success does every day: they identify goals, align them with our company’s goals, and form a mutually beneficial partnership. The skills that allow them to do this transcend all departments. Let’s take a closer look.

Sales skill #1: The shrink

We call this skill the shrink just because it involves going five levels deep to discover what our customers are actually trying to accomplish and the real crux of what they’re doing.

There’s usually a deeper meaning behind why they're looking for a solution. We need to get down into the ‘why’. We can do this by asking the following questions:

  • Why are you doing it this way?
  • What is the goal here?
  • What department is driving this?
  • Is it for you personally?
  • Is it for you to do X, Y, or Z?

Once you ask those questions, you can usually get down to the real heart of why they are looking for a solution and their ultimate goal.

Sales skill #2: Connecting customers’ goals with your capabilities

In my opinion, this is the most important sales skill. We have to connect the dots. Customer success does this every day. This is what sales is all about too. You have something; they need something. They have a goal; you have a goal. Let's match those up and see if it works.

Why you should align customer success, marketing and sales
Customer success is preoccupied with nurturing its current customers, rather than seeking out new customers. While being distinct with different objectives, there is an intersection between customer success, marketing and sales: they’re all customer-centric fields.

One unified message

What frustrates me more than anything else is when marketing tells a story that is completely different from what is being sold.

Ask yourself, when sales development are making cold calls or following up on requests for demos, what message are they communicating? When the customer talks to sales, is it still a unified message? Look at your CRM – does it allow you to document clients’ original asks? Is it facilitating unified messaging across functions?

If that message is not unified, customer success needs to take the reins. Go to each department, go to marketing, go to the exec team, and make sure all of the messaging is consistent from pre-awareness all the way through to renewal.

Typically, the biggest cause of unhealthy relationships between sales and customer success is sales promising things that customer success just can’t deliver. That impacts every part of the customer journey, starting with implementation and continuing through to customer support. There's usually a reason behind this misrepresentation of what our product or service can do, and to find it, we need to go upstream.

Real-world example

When my Customer Success Managers are having an issue or somebody is wanting to cancel, a lot of times they'll take care of it, but sometimes they'll introduce the customer to me. Let’s dig into how I go about solving these issues.

Shrink: Go deep; ask, then ask more

I recently had a customer who wanted to cancel. They said, “We can't do this right now. It's not going to help us. We don't have the bandwidth or the time to put into this.” Going deep, I was able to ask several questions and get to the heart of the issue: the person who ran our solution in their company had left, and they didn't have the budget to replace them at that moment.

Guide: Our capabilities will allow you to do X with Y to get to Z

Once I understood the reality of the situation, I put on my guide hat and re-established their original goals. Luckily, we had their original goals documented and our Customer Success Managers had documented their subsequent goals too. Once I had confirmed those with the customer, I was able to discover whether they had changed.

Negotiator: Why don’t we try this instead of that?

With the customer’s goals re-established, I could start to negotiate. In this instance, as the customer had lost somebody, we were able to take a little bit of extra work on ourselves – call it a professional service. We ran the software for them, which didn't require much effort on our part, and gave them the breathing room to hire somebody new.

That customer is still with us to this day because we were able to use the sales skills I described to get to the crux of the issue.

What makes a good Customer Success Manager great?
At Customer Success Collective, we love hearing from Customer Success Managers. In fact, we’re obsessed with them and the work they do; our small contribution is to create a hub of educational resources for global CS enthusiasts.

Organization-wide methodology

Without a goal, you can't establish success. Now, a goal is one thing, but if you don't have metrics surrounding that, how are you going to measure that success?

In our organization, sales will not progress a deal until they have established a quantifiable goal from the customer. Maybe they want our product to save them X number of dollars, generate Y amount of revenue, or save Z amount of time. Without that measurable goal and the relevant metrics, we don’t sell.

That’s just one of the ways that we ensure that we can align with the customer’s needs. Now I’ll walk you through five questions that will help you to do the same and get your whole organization singing from the same sheet.

What are your capabilities?

As I mentioned earlier, a major part of our role in CS and in sales is aligning our capabilities with the client’s problems. We're not solving their problems; we're facilitating the solution. The client is solving their problems using our tools or capabilities.

Do you know and have listed all of the capabilities of your product or your offering? If you don’t have an established list for customer success, sales, marketing, and every function that touches the client, you cannot do a good job of aligning your capabilities with the potential needs of the client.

You’re looking to create a consistent message, beginning with marketing and continuing throughout the customer journey, so those capabilities need to be very clearly identified. This is going to help you not get those handoffs where somebody is sold on something that's completely different from what you actually do.

What problem is your client trying to solve?

If the client is trying to solve a specific issue, you need a way to document this in your CRM, so that implementation, customer success, support, and everybody who comes into contact with the client knows what that issue is.

If that's not documented, it's going to be tough to know what assistance you can provide and to help them understand how to match your capabilities with their goal. If you don't have a way of documenting this, and it's not consistent across the board and reaffirmed to the client every step of the way, I’d recommend getting that done.

Does your client have a goal specific to this problem?

With your client, you need to establish a measurable goal. That will make life so much better down the line. If your client doesn't have a number, how are they going to get the budget for it? More importantly for CS, how are they going to justify keeping the budget for it?

Sometimes people purchase solutions on a wing and a prayer and they have no idea if they're going to generate any savings or revenue or save any time. That’s when you hear, “We just don't think it's working out,” and you have nothing to measure that against.

If you’re not actively getting that goal and the metrics surrounding it, you're doing your future self a disservice. Establishing a goal right at the beginning of the journey is the only way you can measure whether or not your client is truly successful using your capabilities.

How does your capability help the client solve their problem?

We provide an offering to help the client do their job. That's why they're willing to pay us. Now we have a clear vision of our capabilities and the client’s goals, we can hopefully match them together and help the client to solve the problem they’re coming to us for help with.

Say it out loud: Would having X capability, which allows you to do Y, help you to solve your problem and meet your goal of Z?

Throughout the sales cycle at Roster, we use this very simple question to ensure that our capability can help customers to solve their problems and meet their goals.

The answer is: typically, yes, so long as you've followed the first four steps correctly. That is such a powerful statement for the client to agree to. "Yes, that capability is exactly what I'm looking for, and I do believe having that capability will help me to solve my problem and meet my goal."

We've built our entire business on this methodology, from marketing to sales to business development to pre-sales, and even pre-awareness. We make sure that we are very clearly communicating the full scope of what we do so that the client can make an informed decision and be very clear every step of the way that yes, they want what we can offer.

Final thoughts

In my opinion, sales and customer success are so closely aligned there's almost no gap there at all, and there shouldn't be. A good salesperson is just using the same philosophies that a good customer success person is using: making sure that we understand the true needs of that client and our true capabilities, matching those up, and making sure that they can be successful.

I urge you to establish a unified message via the chain. If marketing isn't telling a story that matches the way you see clients using your product, you have got to be that voice in the executive team making sure that everybody's on the same page.

Sales, we love you. Customer success, we love you. We're all working towards the same goal: making sure that the client is getting out of the solution what they need.


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