Becoming an Enterprise CSM

Becoming an Enterprise CSM

If you’re one of the many people who’ve entered Customer Success in the last 1-2 years, you probably have the itch to advance your career. The good news is, our domain continues to boom. However, industry growth and a crowded field can make it feel difficult to know how to stand out and, focus your time, and grow.

One potential area for growth is managing Enterprise accounts.

This article will cover the key differences between SMB and Enterprise Customer Success Manager (CSM) roles, how you should position yourself for a move, and what to expect when you get there.

The theme is to be strategic!

As an up-front disclaimer: a CSM role is an excellent launching pad into a variety of different roles. Working as a CSM can equip you to move into leadership, analytics or program management, and any one of many cross-functional careers. Also, managing an Enterprise segment isn’t necessarily a promotion over managing an SMB segment (although in most company hierarchies, it’s defined as such).

The truth is, managing different segments calls for different skill sets. While moving from SMB to Enterprise might be career growth on paper, it might also remove you from a position that caters to the best of your abilities.

With that said, let’s walk through some differences and how you can plan your next move.


As a CSM serving an SMB market, your customer list is probably too large for you to give personal attention to everyone. Your customers probably interact with your company digitally, and you supplement with a human touch when needed. Here, you’re playing a numbers game: your leadership designs the best program they can, you run it, and you see what the results look like along the way.

At the Enterprise level, you’ll have a much smaller customer list - probably somewhere between 1-20. You should expect to interact with your customers on a personal level most of the time, whether that means in-person, by phone, or with individual emails sent manually. You can supplement your outreach with a digital program, but even those messages will likely require personal follow-through. This is not a numbers game. Losing one customer can be devastating to you and your company, whereas meeting NRR goals can secure a future for you both.

If you’re looking to make the jump from SMB to Enterprise and want to prepare yourself, focus on how you think, strategize, and communicate when you interact one-on-one with an SMB customer. Practice asking open-ended follow-up questions to gain a deeper understanding of the client’s wants and needs.

If you don’t carry a retention or expansion goal in SMB but Enterprise CSMs in your company do, you can still practice your skills in your current role. Getting someone to adopt an idea or take a certain action is a great way to “sell” to your current customers even if you don’t carry commercial responsibility.

Contacts and multi-threading

At the SMB level, a sole proprietorship legitimately has 1 contact; even a mid-market customer may only have 1-2 people for you to know in the department your solution serves. Often, these contacts aren’t experts in your company’s domain, or in using your solution - consequently, your challenge is often to educate them.

On the other hand, Enterprise customers typically have many people you need to cultivate close relationships with. Why? Because they all play a role in your ability to retain and grow the customer. You’ll have decision-makers, coaches, promoters, detractors, end-users, front-line managers, and so on. You must know who they are and how to manage their perception of you as a vendor. You’ll also need to understand what kind of internal politics they may be engaging in with each other!

Because Enterprise customers employ so many people, there are often specialists who use your solution every day. Those individuals may know their way around better than you do or are more in touch with industry news than you are.

To prepare yourself at the SMB level for the next step, be curious about new contacts who might be involved with your product - even mom-and-pop shops have external IT consultants, graphic designers, and finance vendors who might affect your ability to retain and grow. Take advantage of every webinar, lunch-and-learn, or internal LMS track you can in order to keep familiar with your product’s UI. Think about what success means for each contact and use that as the north star for each contact relationship.


You’ve probably heard the phrase “be more strategic” at some point before reading this article. Here’s where the real difference between SMB CSM and Enterprise CSM work is... between your ears.

As an SMB CSM, you’re monitoring your customers as a group, and your personal interactions with customers tend to be tactical and transactional. Escalate the tickets, run the reports, generate the renewal quote, and so on.

An Enterprise CSM who spends more time in the weeds is almost certainly not spending enough time being not busy. Specifically, in order to “be strategic”, you must listen and reflect. Listen and get the most out of your conversations with your customers. It may take time and practice, but you’ll become comfortable with asking for and surfacing their true pain points. Then, reflect on the bigger picture. How will your next action play out in reality? Will it truly support your executive sponsor’s desired outcome? Are you prioritizing it appropriately? Spend time on what matters. The rest is noise.

There’s no magic practice tip for this one - it’s a mindset and you can have it no matter what your role is today.

Final thoughts

Overall, Customer Success is about delivering desired outcomes to customer contacts regardless of their segment or revenue level. The only thing that changes as you move across segments is the “how”. Having a CSM mindset is most of the battle, and switching from an SMB mindset to an Enterprise one is the home stretch.

Latest Posts