A Guide for CSMs Nervous About Selling

by | 2 Dec 23

A few months back, I got curious and decided to run a little survey on LinkedIn. It was a survey that focused on Customer Success Managers (CSMs)! And this blog is for you CSMs too. Yep, you! The super important folks who keep the wheels turning in our businesses.

In the survey, I was eager to know – what’s the toughest part of your job? Guess what? Out of 280 responses, just over 100 CSMs said it was “upselling and cross-selling.”

But here’s the good part – I’ve got something to share with you. If you’re a CSM that has a responsibility to generate revenue through upselling and/or cross-selling, I’ve found a way to make the act of selling more comfortable and believe it or not, the process of learning this is even quite fun.

Ready to get started? Let’s go!

Table of Contents

Use these links to jump straight to the part of the article that interests you most.

> A Brief History of The CSM Role
> How To Get Better And Feel Better
> What’s Good and Bad?
> To Summarise

A Brief History of The CSM Role

Over the years, I’ve had the pleasure of working with some truly amazing CSMs.
Over that time things have changed in the Customer Success world.

Let’s jump in the time machine and go back about a decade – remember when CSMs didn’t have to worry about hitting revenue targets? Ahh, those were the days, weren’t they? Hmm, not really.. a CSM job mostly involved putting out fires, dealing with customers on the brink of walking out the door, and doing their best to keep them onboard.

But then, something started to change. People began to notice that these hardworking CSMs were doing more than just keeping customers from leaving. They were building genuine relationships, and providing real value. And guess what? The customers noticed too. The customers were achieving more in their roles because of the products they bought and the help they were getting. That translated into higher retention rates, more referrals, and increased upsells and cross-sells. Happy times!

Now, here’s where it gets interesting. The upsell and cross-sell part usually kicked in when a savvy CSM spotted an opportunity to introduce a customer to a salesperson. This salesperson would then add even more value by showing an upsell or cross-sell product that could solve a problem the customer was facing.

But then, the game changed again. Businesses wanted to speed up the sales cycle and lower the cost of sales for these upsells and cross-sells. So, guess who got the sales targets? Yep, the CSMs. They were now expected to take the opportunity all the way to the finish line – from spotting the chance to closing the deal.

And this is where the challenge comes for some CSMs. Remember the 100+ CSMs from my survey who said upselling and cross-selling was the hardest part of their job? It’s because selling isn’t necessarily second nature for those in a CSM role.

But don’t worry, I’ve got your back. Here’s how you can tackle this head-on…

How To Get Better And Feel Better

Here’s an invaluable tip to help you conquer the fear of selling: get yourself more demos from other software suppliers. Sounds a bit strange? Stay with me, it really helps…

Perhaps you’ve heard about Monday.com but you’re not quite sure what all the excitement is about. Or maybe you’ve seen mentions of Jasper.ai and you’re curious to know what it actually offers. Or perhaps there’s a product you’re already using and you’re considering paying extra for additional features… My advice? Don’t hesitate – go and book that demo.

Of course, there’s a bit more to this process than just watching a demo (more on the ‘What’s Good and What’s Bad?’ section below). But your first step is to visit the websites of some impressive software you’d love to explore, and book a demo!
Now, a word of caution – you’ll likely find yourself in the salesperson’s pipeline, and they may follow up with you. And yes, you might have to say no. But trust me, it’s worth navigating this because you’ll gain a load of knowledge about overcoming the fear of selling.

And here are two amazing things about seeing these demos:

  1. You get an in-depth look at some really engaging pieces of software
  2. You experience, firsthand, the good and bad of a sales experience

I suggest you aim for about 6 to 10 demos. This gives you ample opportunity to witness the good, the bad, and everything in between.

The goal here is to identify what makes a salesperson effective and what doesn’t. And believe me – as a CSM, you’re better equipped for this task than you might think. Let’s dig deeper into that now…

What’s Good and What’s Bad?

This is actually quite simple. Once you get the hang of it, it’s a breeze to not just sell but to identify potential selling opportunities.

The key to a good sales experience is this: does the product fix a problem the customer is dealing with?

So, as you sit through these demos, keep an eye out for what an effective salesperson should be doing. They should:

  1. Take the time to truly understand your current challenges and difficulties.
  2. Dive deep into your ideal future scenario (essentially, if the above issues were resolved, how would things dramatically improve for you and what positive impact would it have?).
  3. Demonstrate in the demo that the product can solve your problem and lead you to that ‘perfect future’.

That’s all there is to it. Just these three points. It’s as simple as that.

So, when you’re on these demos, keep these three points handy and see if the salesperson ticks all the boxes. If they do, then they’re good! Hooray! But if they don’t… well, you know what that means… they end up in the not-so-good pile (eeeek).

Did you notice something? As a CSM, these three points directly relate to your daily tasks. You’re already helping customers overcome challenges and achieve success. The only difference here is that you’re usually discussing a product, feature, or service that they’re already using. Quite a revelation, isn’t it?

So, To Summarise

Go ahead and schedule 6 to 10 demos. Keep the 3 key points above in mind and evaluate if the salesperson is hitting them.

By repeating this process, you’ll get really good at judging – from a customer’s viewpoint – how it all feels to be ‘sold to’.

And believe me, when the person giving the demo is sincerely dedicated to solving a problem you have, it won’t feel like a sales pitch. Instead, it will feel like you’re collaborating to figure out how you can achieve greater success.

Now, that’s not something to be scared of or to worry about. In fact, it’s pretty much what you’re already doing every single day.

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