A CSM’s Guide to a Career in Sales: Why the Switch Might Be Worth It.

Change can be scary, but often it’s a necessary step for growth.

My journey from Customer Success (CS) to an Account Executive at Planhat is a testament to this.

Until my current role as an Account Executive at Planhat, I spent my whole career in Customer Success. I joined as the first Customer Success team member, built the team to ten people strong, and got a series B under our belt.

I love CS, the community that’s been built, and every customer I’ve worked with (even the challenging ones!), but I knew it was time for a new challenge.

Why Transition from CS to Sales?

There are many reasons why a CSM would want to move into sales.

1. For those aiming to become revenue leaders, sales experience provides a comprehensive understanding of the company's Go-To-Market (GTM) strategy, from the initial cold calls to the customer renewal process. This experience builds a new skill set and broadens your understanding of the business.
2. If your goal is to work your way into CS leadership, even a Chief Customer Officer position, having exposure to both the CS and the sales process can be a significant advantage. This can round out your skill set, making you more versatile and equipped to handle revenue responsibility, whether you stay in sales long-term or return. As Customer Success roles increasingly involve revenue responsibilities, having a background in both areas could give you a unique edge.
3. Of course, there are also many financial reasons you may want to transition into sales. If you hit or exceed your targets, you can make more than a typical CS role. This comes with the risk of a large portion of your salary being tied to a commission. Some thrive in this environment.

For me, all three reasons above contributed to why I made the shift. I’ve always had an entrepreneurial drive to create. Customer Success has become my passion throughout my career, so I knew a transition to sales, while getting to talk about Customer Success every day, would be perfect. That way, I could get the necessary experience and skill set to one day become a revenue leader, customer advocate, and founder.

How Do You Know if You’ll Be Successful in Sales?

Moving from a CSM to a BDR (Business Development Representative) or AE (Account Executive) comes with challenges and many advantages. First, let’s start with a few qualities that make a great CS professional. The best CSMs have:

• A strong sense of empathy for their customers
• A knack for solving difficult problems with creative solutions
• An obsession with customer outcomes

Guess what? The best Account Executives excel in these traits as well.

Being a transactional AE or CSM doesn't cut it anymore. You need to understand the problems your customers are trying to solve, map out the path to success, and ensure you track progress toward that success even after the deal closes. Stay involved, even if that means just checking in occasionally. Both the customer and the CSM will appreciate it.

I’d define the major difference between sales and CS by your relationship with your customer/lead. In Customer Success, for the most part, you will be the “good cop.” You’ll be the Voice of the Customer and relay feedback and will generally do what you can to make their experience as great as possible.

In sales, you have to be prepared to push back on objections. You can’t sell complex B2B software on relationships alone, there is more nuance than that. It requires creative thinking and the ability to change old ways of thinking. You are there to be their friend, but at the same time, it’s important to get your prospect to buy into why your new solution is better than their current way of doing business.

If you’re wondering if this is something you’d be up for, I’d highly recommend reading The Challenger Sale by Matthew Dixon and Brent Adamson before accepting a new role. You'll learn quickly if you are comfortable with this, but I promise you can. Take control of the conversation and be that trusted guide.

The Reality of Working in Sales

With any career change, you’ll face new challenges and be expected to move fast and learn even faster. Whether you’re starting as a Business Development Representative (BDR) or Account Executive (AE) or moving straight into an AE position, here are a few realities you have to come to terms with:

Reality #1: You Control Your Schedule

Customer Success Managers, especially ones at full capacity, are bound by customer engagement requirements and a heap of internal meetings with product, support, and sales…you get the idea. CSMs juggle 100 priorities with many different internal and external stakeholders.

However, when you move into sales, your calendar will open up much more. This brings the need for excellent time management, discipline, and accountability. Block out time on your calendar every day to prospect, update your deal statuses, and send agendas for the next day of meetings. The rest of your time outside meetings should be spent generating pipeline coverage for the current and next quarters.

Reality #2: Your Performance is Constantly Monitored

Don’t get me wrong, Customer Success is also metric-driven. However, in the history of SaaS, CS is the new kid on the block. Selling has existed for thousands of years, and there have been tried and tested KPIs that result in predictable pipeline and revenue.

Be prepared to have a plan on how you’ll reach these metrics consistently and generate enough pipeline that you have multiple routes to reach your quota.

Even if you’re not closing deals from day 1, show that you can book meetings, run demos, and move stalled deals forward. If you can do that well, things will fall into place eventually. Your team will know who is working hard to improve, even if the closed deals aren’t there yet.

Reality #3: You Decide When to Pursue or Move On From Deals

When you’re in CS, you try your best to enable and guide your customers to be successful with your product.

In sales, it’s about the art and science of knowing when to persist with a deal and when it's more strategic to move on. You will have a quota to hit and a pipeline to generate, so using your limited resources on a deal with a low chance of closing will stop you from reaching your targets.

This isn’t an easy mindset shift for CSMs because it’s our DNA to want to sell a solution that will fully work for our customers. In sales, this is important too, but you will feel the pressure to get the contract signed.

Reality #4: Your Income May Fluctuate Month to Month

You might be accustomed to a steady base salary with predictable monthly earnings in Customer Success. However, your income can vary significantly in sales from one month to the next. This is because a large portion of a salesperson's compensation is often based on commissions directly tied to your sales performance.

While this can mean the potential for higher earnings when you exceed your sales targets, it also means that your income could decrease in months when sales are lower. This requires mental adjustment and financial planning to manage the ebb and flow of a commission-based income.

Ready to Make the Transition?

There are plenty of similarities between CS and sales, but it comes with many differences. If you’re going to make the transition, you have to get used to a few things, including:

• A change in team culture
• Commercial negotiations
• Multi-tasking top-of-funnel lead generation and closing deals
• Cold-calling hundreds of strangers
• Irregular income streams based on when you’re closing
• Loads of rejection

If you’ve read this far, you’ve already checked off the biggest box: the interest and willingness to dive in! I promise if you work hard, learn fast, and are willing to fail, you’ll be successful.