How Do I Break Into Customer Success?

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By Steve Schwartz

Building on what Ashley brought us in her 3-part series on Searching for Success, I frequently get asked by job seekers early in their careers “how do I break into Customer Success for the first time if I’ve never done it before?” While I may have taken one of the more straightforward routes to find myself here, I know that there are many possible ways to find your first job in the field. I’ve heard a lot of common themes about why people feel they aren’t qualified to even apply to certain Customer Success jobs. I offer the following advice to those who are struggling to break through and I hope it can help you find your way.


This is one of the biggest misconceptions people have about themselves when it comes to Customer Success. Have you ever worked as a server or bartender in a restaurant or in a retail store of any kind? Then you’ve done what I’ll term real-time Customer Success. So how do you show that with a resume and cover letter?

Construct a master resume with as many bullet points about each job as you can, including metrics and milestones you’ve hit, KPIs you’ve been measured against and how you delivered, new skills you’ve acquired, projects you’ve led and delivered, and anything else you might ever want to highlight. For each job you apply to, take the specific job requirements and skills they are asking for and pare down that resume to one page, with the bullet points focused on matching your experience with those requirements. Then use the cover letter to get into more detail about how those things align and make sure you show what you know about, and are interested in, the company (“do your research” as Ashley says!).


Don’t let this stop you from applying to a job that says it’s required or preferred. If you can show me that you can learn new technology or a new industry through your experience and passion, I’m listening. If you back that up with the key skills that I’m looking for like, strong and empathetic communicator, analytical and critical thinker, and self-motivated learner, I’ll believe we can teach you the product and industry. In my experience, bringing a new hire with customer skills up-to-speed on a product is far less risky than trying to turn an industry expert into a customer-facing professional.


You’ve applied to companies that you’re passionate about, but haven’t been able to break into the Customer Success team directly. What do you do next? Do you broaden your search or is there another option? Are there entry-level roles at the company such as support, sales development, or lead generation? Because these roles are typically fast learning and have high turnover, they will give you an opportunity to gain valuable product and industry knowledge, exhibit your customer-facing skills, and showcase your analytical abilities in a very short period of time. Good managers of these teams will recognize that they won’t be able to keep you for long and should be empowering advocates for your transition into another team, whether that be Customer Success or anywhere else that your passion and knowledge can benefit the company.

If you’ve made it this far and you’re passionate about electric vehicles, electrification, or energy storage, I’m hiring a Customer Success Manager to join my team at FreeWire.

Are you a new CSM or looking to break into the field? The Success League offers a complete CSM Training Program that can provide you with practical tools to strengthen your professional toolkit.  For more information on this program and our other classes and workshops, please visit

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Steve Schwartz - Steve is a customer success leader who enjoys starting and building high-performance teams at early-stage startups. He has worked in energy startups for the past 10+ years in a variety of customer-facing roles. By engaging with customers during the sales cycle, he ensures customer expectations are fully understood and can be exceeded. When not writing for The Success League, Steve is leading Customer Success at FreeWire Technologies. He holds a BS from Tufts University and an MS from Virginia Commonwealth University, and spends his free time with his wife and two kids exploring the Bay Area.