5 Easy Steps to Teach CSMs to Sell – Without Selling Their Souls

By Rachel Provan
Teach CSMs to Sell

Want to teach CSMs to sell? It might not be that easy. Here’s why:

Most customer success managers hate sales. They see it as sleazy and manipulative, and not in line with what Customer Success is there to do.  

CS tends to see itself as virtuous. We’re here to help the CUSTOMER! Not ourselves. When they win – we win. Being told we have to sell can feel like we’re being asked to compromise our integrity.  

Good news – what we’re thinking of is BAD sales. There’s a way to sell that is completely in line with the spirit of customer success.  

Now is the time to teach CSMs to sell. Because it doesn’t help your customer if your company goes under…

Come on. Let’s save the day! 

The line between sales and customer success is getting blurry

Customer success has always been on a pendulum.  

It started out as high-touch consulting for large enterprise customers. Over time, it swung all the way over to the other end to the scale customer success model. Valuation was high, and companies were growing so rapidly, they needed to be able to make more customers successful – fast.  

Suddenly, new business screeched to a halt.

And now there’s a new focus – stay afloat at all costs.  

Roles that were once focused on the customer relationship are now focused on the bottom line.

Whether we like it or not, it’s time to get revenue focused.

Protect your CS department from layoffs

CSMs are getting laid off left and right. It’s heartbreaking. The issue is that they are either seen as a cost center, or a “nice to have”.  

The value of customer success is not always understood. Most companies believe that if a customer bought the product and we showed them how to use it, the customer should stay. That’s just logical.

And it is… if you weren’t dealing with humans. Humans don’t behave predictably, nor do we know what is going on in their lives and businesses to affect their behavior. That’s why “set it and forget it” doesn’t work.  

Not only do you have to teach CSMs to sell… as their leader, you’ve got to do some selling yourself! But of the internal variety…

If you want the C-suite to pay attention, calculate how much of your revenue is made up of returning customers, vs. new logos who are in their first year with your company? Who generates more year over year? Or you could send them this article which gets in even deeper about why expansion revenue matters for long-term growth.

CS is usually responsible for approximately 90% of revenue at most SaaS companies. Once you point that out to the C-Suite, they suddenly realize how important your team is!

In this market, Sales teams can’t sell. Customer Success can.

It’s not their fault. Sales is out there killing themselves trying to bring in new clients right now. But with a looming recession, inflation, and all that other fun stuff, most companies have locked down their spending on new tools.

The name of the game right now is consolidation. Do as much as you can on a few tools, rather than having a lot of tools that just do one thing.  

If your product can do multiple things, using your platform to do them all might actually save the customer money since they will be able to pay for one tool vs many. So if you’re worried about asking your customer to pay more in this economic climate, that’s not what you’re asking them to do at all. You’re right in line with what they’re being tasked with – whether they’ll admit it to you or not.

Retention is Harder

Don’t think retention goes out the window! Right now every single saas tool on the budget has a question mark next to it. Unless you’re Salesforce or SAP… you’re at risk. You MUST have a way to ensure you’re delivering major value – and that your customers know it! Find little ways to remind them of the value they’ve realized over regular intervals. I’ve had huge success using the tactic below:

If you don’t steal this you’re a fool

Figure out the value of common actions customers perform in your product. Figure out money saved, time saved, attacks blocked, etc.  

Then have a banner or email every quarter that says “Hey [customer]! You saved [61] hours this quarter by using [Company]! “

Then in small print – (“You’ve [completed X action] 562 times in the last quarter. Our studies show that averages out to around 6.5 minutes saved per use. Amazing!) ”

Expanding the Customer Base From Within

It’s often said that it’s easier to sell to an existing customer than a new one. This makes a certain amount of sense because, if your customer success manager has done a decent job, the customer knows and trusts them, and knows your product delivers value.

There are many different ways you can add to the company’s bottom line

Cross-selling best practices

Learn how different verticals use your product.  Find their specific use cases and cross-sell them. It will be a lot clearer how else your product can help! You’ll be surprised how many cross selling opportunities there are just based on different use cases!

Upselling best practices

Increase the number of customers you can reach. 

Can different departments in the same company use your product?  

Don’t be afraid to ask upsell questions! Identifying up-sell opportunities doesn’t have to feel awkward. Ask about what other problems the company is trying to solve. Even if it has nothing to do with your product. There might be ways it can be tied in that the customer hasn’t thought of yet.

Increase the customer base through renewal and advocacy programs

Social capital matters. If you have a customer who truly loves your product and has benefitted from it, they’re probably happy to recommend it! But rather than just being a reference for sales – have an incentive program.  

Make it worth their while to tell a friend about your product. Whether that’s a month free for them and the new client, an additional service, or something else that might benefit them.  There has to be something in it for them!

Selling new products to existing customers

If your product team has come out with a new product, make sure every one of your clients knows about it. You don’t have to get pushy with them – just make them aware that the product now exists, and what the benefits are

Selling professional services 

Not everyone has a professional services team, but if you are lucky enough to, don’t skip it just because it’s not recurring revenue. It still contributes to the lifetime value of the account.

If clients complain about being stressed (and they all do!) have the customer success manager say “I know you’re swamped. If you want, we can take X off your plate for you so that you can handle XYZ…”

Why Most CSMs Hate Sales

It’s not complicated. Most CSMs hate sales because… they’re not salespeople!

People generally don’t like doing things they are bad at.

Just as someone from marketing wouldn’t do very well if you threw them into the engineering department, a CSM with no sales training is probably going to crash and burn.

CSMs are people pleasers. They want to make their customers happy and they don’t want to rock the boat. They’re afraid of being pushy or making key stakeholders uncomfortable.

That’s because they’re thinking of bad sales…

Bad Sales 

Unfortunately, too many sales trainings today still focus on “bad sales”. We’ve all had negative experiences when interacting with a pushy salesperson. That’s because they’re been taught to focus on things like:

White space

This is a way to look at accounts to see what they have and haven’t bought yet from your suite of projects, and angling in to fill in the “white space”.  

Guess what? Not all customers need every single thing you sell. And if you try to sell them on everything, they’ll get annoyed. Focus on what would truly benefit your customers and work with only those offerings.

Objection Handling

This one tends to make CSMs squirm – and for good reason. No one wants to be “handled”. They want their thoughts to be respected. It sounds manipulative.


Much of objection handling (or sometimes the whole process) is done through scripts. Pre-written answers to common objections. These are so generic, it’s no wonder they never quite hit right. There’s nothing authentic about them.

Closing techniques

Even those who haven’t seen the movie Glengarry Glen Ross still know the scene where Alec Baldwin struts around a dingy sales room telling all the salesmen to “ALWAYS BE CLOSING!”  

So what is closing? Asking for the sale. Usually in a way that would make anyone cringe.  

It’s asking “So did you want to start the implementation Thursday or Friday?” When the customer hasn’t even indicated they wanted to buy yet.

Good Sales

Good sales is not far off from traditional customer success. It’s about listening and understanding the customer’s needs – sometimes even more than they do.  It’s not about taking advantage of your relationship.

It’s about proactively helping customers avoid mistakes. It’s looking out for them and showing them their blind spots. 

You know how people call CSMs strategic advisors? Good sales is exactly how we can embody that. 

When you use the method outlined below, the customer will come to the conclusion themselves that they need to solve their problem with the solution you provide, and they’ll feel taken care of.

How to Teach CSMs to Sell

The method I use below is stolen shamelessly from Neil Rackham. Go read his book SPIN Selling. It changed everything for me. I have some influence from a couple of other books too, but here’s how I sell today – and how I teach CSMs to sell:

1. What’s the problem?

When the customer mentions a problem an upsell can solve, STAY CALM! Do not jump in with “We have a product that can help with that!” It’s unlikely they think it’s that big of a problem. Use your superpower:

2. Empathize 

Let them know you get it. Understand their frustration.

3. Pull that Thread – (Implication questions)

Most of the time, your client will think of the problem as fairly minor. That’s because they’re looking at it in isolation. They haven’t realized the dominos it will set in motion.

Ask questions that point to other problems that might arise from the issue. I like to think of this as “What other problems is that causing you?” asked a few different ways. You can ask things like:

  • Is that impacting anything else?
  • Is that causing bottlenecks?
  • How much time is that taking up?
  • Has that happened in the past?
  • How long did it take to solve it?
  • Do you think it will happen again?
  • How much will it cost to fix it?
  • How is that affecting your team?
  • Is that affecting your commitments to your stakeholders?
  • Are you still able to reach your goals while you have to deal with all of that?

Don’t ask ALL of these in the same selling interaction. Pick a few relevant ones or ones like them. You just want to keep the customer from shooting themself in the foot by thinking things will be fine. You’re not being manipulative here. You’re protecting them.

Now let them know you might have something that can help them, but you have a few more questions.

4. How could it help if you solved this?

Realizing the extent of the problem can make people a little anxious. Make this a positive conversation by not only exploring the problems but highlighting the benefits of fixing them.

Just as the questions above highlighted how additional problems happen if the first one isn’t fixed — ask similar ones about benefits:

  • What would you do with the time you got back from fixing this?
  • How would fixing this problem impact your bottom line over time?
  • Would fixing this improve team morale?
  • Would it be easier to collaborate?
  • How much easier would it be to achieve your goals?

5. Do you think this needs to be fixed NOW?

Everything action we take has consequences – including NOT taking action.  

Would a small problem grow into a big one? What opportunities are you leaving on the table by not fixing it?

Once the customer has stopped saying they “should” fix it, and has started saying they “need to fix it now”, offer them the chance to do that with your product. 

Want CSMs to Sell? Pay them for it.

This shouldn’t come as a surprise. CSM-ing is hard enough. Asking CS to do all the legwork of setting up the sale – only to let an account manager earn the commission for filling out the paperwork – doesn’t incentivize the CSM at all. If you want CSMs to add selling to their already long list – there needs to be a financial motivation. 

I’m a fan of an 80/20 split of base pay plus variable – with the variable being based on renewal and additional commissions for upselling/cross-selling.

This makes sure the CSMs focus on KEEPING the clients and feel driven to increase their sales to increase their paychecks.  

Another thing to keep in mind here as an extra incentive – (in the USA at least), bonuses are taxed at around 50%. But commission is considered salary and is taxed generally around 25%. That’s not hard math to understand.  

Developing a New Skill Doesn’t Happen Overnight.

Don’t expect instant results. No matter how clear it may seem to them the moment they learn it, when it comes to putting these tactics into practice, they will stumble all over themselves. This is normal. Make sure they know that.  Keep encouraging them.

Their best bet is to work on one area at once. Think of 3 new problem questions to ask and try them out on a couple of clients. Get comfortable with one step before moving to implication questions.

Don’t expect the same results from everyone. People learn at their own pace. This is a new skill, and it’s an art form that can always be refined. It’s not a race.

Practice Together

The best way to learn something new is by doing it, and the same applies to selling. The best way for your CSMs to become better salespeople is for them to practice in low-pressure situations.  

Pair them up and have them practice with each other 1:1 and give feedback about what worked well and what could use improvement. Do this round-robin style. Over time, patterns will emerge for each of them about what their strengths and weaknesses are, so your training can become more targeted.  


This method of selling is based on two things cobbled together:

 Neil Rackham’s “SPIN Selling”, and

Never Split the Difference by Chris Voss.  

I recommend every CS leader and CSM read them at least once. SPIN is a quick read, and completely changed my views on selling – and my close rates – practically overnight. It’s the ultimate guide!

Never Split the Difference is absolutely riveting on audiobook. Plus it’s about hostage negotiation… hopefully your client calls never come to that, but better safe than sorry…

This article from Gainsight on upselling is a great read too!

Cheat sheet:

In case it’s helpful, here is what I used as my cheat sheet during client calls. These aren’t to be used verbatim – it’s more to remember the order of the conversation and the types of questions to ask:

  • What’s the situation?
  • What’s the problem?
  • How else is it a problem?
  • What else might that affect?
  • How would fixing it help?
  • What other benefits are there to fixing it?
  • What happens if you do nothing?

This Challenge is an Opportunity

While it may feel like unreasonable pressure, it’s important to have a growth mindset here.  

When done well, this cements your seat at the table with the Executive Leadership Team.

You have the chance to save your company right now. This is not an exaggeration.  

This is Customer Success’ moment to shine. Not by doing someone else’s job – but by doing what we do best: helping our customers.

Whenever you’re ready, there are 3 ways I can help you:

1. Move from CSM to Management with my proven success map here.

2. Land your dream job in Customer Success here.

3. Establish yourself as a world-class customer success leader— Hone your strategy, lead with heart, and create work-life balance here.

This post contains affiliate links. If you use these links to buy something I may earn a small commission. Thanks.

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