Customer Success Career Advice: Stop Blindly Following Traditional CS Paths

CLICK PLAY TO HEAR WHY YOUR CUSTOMER SUCCESS CAREER FEELS STUCK WHEN YOU FOLLOW THE DEFAULT PATH:

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Here’s what you can expect from this episode:

What if the reason your Customer Success career feels harder than it should has nothing to do with your skills, your effort, or your results and everything to do with the path you’re blindly following?

In this episode, I’m challenging one of the most common (and costly) mistakes I see CSMs make — assuming the next step on the traditional career ladder is automatically the right one. Enterprise. Management. Bigger accounts. Bigger titles. More money. On paper, it all sounds like progress. But in reality, following a path just because it’s familiar or expected can quietly lead you into roles that drain your energy, stall your growth, and cap your long-term earning potential.

I break down why so many high-performing CSMs end up bored, frustrated, or stuck after a promotion they thought they wanted. We talk about the hidden downside of chasing titles without thinking about the day-to-day work, the false belief that there’s only one definition of success in Customer Success, and how “doing what everyone else does” can pull you further away from the work you’re actually good at. I also share personal stories from my own career (including a role that looked like a win but felt like a mismatch) and patterns I see over and over again in CSMs who come to me feeling lost or disillusioned.

This episode is also about possibility. Customer Success is one of the few roles that touches nearly every function inside a company (product, sales, marketing, support, enablement, leadership) which means your career options are far wider than you’ve probably been told. We explore what it looks like to define success on your own terms, whether that means staying an individual contributor long-term, specializing in a specific part of the customer journey, moving into enablement or product, or leaning into newer paths like tech-touch customer success. Instead of asking “what’s the next step,” I’ll show you how to start asking a better question — where do I actually want this path to take me?

By the end of this episode, you’ll have a clearer framework for making intentional career decisions. Ones that align with what you enjoy, what you’re good at, and how you want your life and career to feel. If you’ve ever said yes to a role because it felt like the only option, questioned whether you really had a choice, or wondered why success doesn’t feel as satisfying as you expected, this conversation will help you reconnect with your agency and take control of your career direction. Press play now because the most important career move you make might be deciding to stop following the path you never chose in the first place.

Topics covered on why your Customer Success Career feels stuck when you follow the default path:

• Why blindly following a traditional career path in customer success can leave you stuck and unsatisfied (and what to do instead)
• How to identify if you’re on autopilot and three stories of CSMs who realized too late they made a move they didn’t actually want 
• The power of intentionally defining your own version of success in customer success (and why no, you don't have to become a manager or move to enterprise) 
• Why your exposure to every team as a CSM is a secret weapon and how to leverage it to pivot in almost any direction, from product to enablement to brand-new roles
• A breakdown of Tech Touch Customer Success, why it’s the most exciting up-and-coming career path, and how you can become a thought leader fast in this space 
• The one interview question you should ask a future manager to spot red flags before you accept an offer

When you’re ready, here’s how I can help you land a job in Customer Success despite all the competition:

• 1:1 Career Coaching Program – Get personalized support to land your first Customer Success role or finally step into your dream CS job.
• Free Training: Optimize Your Resume for Customer Success Jobs – Transform your resume so it gets noticed and starts bringing in consistent interviews.
• Free Training: Sell Yourself in Interviews – Learn exactly how to position yourself as the top candidate and walk into every CS interview with confidence.
• Free Training: Master Behavioral Interviews – Discover a proven method to answer every “tell me about a time” question and impress any interviewer.

Connect with Carly:

• Connect with me on LinkedIn 
• Email me at [email protected]

Want more on this topic? Here’s your next listen:

• Episode 31: 4 Exciting Customer Success Career Paths To Consider
• Episode 20: How to avoid a bad fit role (PART ONE)

More about Customer Success Career Coach:

Customer Success Career Coach is the must-listen podcast for current and aspiring Customer Success pros. Join Carly and her guests as they spill the secret strategies and tips for building your Customer Success career. This isn't your typical snooze-fest – they’re diving deep into the world of Customer Success careers. Whether you're starting from scratch (hey career transitioners!) or eyeing that next big promotion, they’ve got the playbook for you. Every Wednesday, join Carly and her amazing guests as they dish out practical advice and real-life steps you can actually use. No fluff, just stuff you can apply ASAP to score that dream job, snag that promotion, or become the team rockstar.