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The economy has been turned upside down, and technology companies across multiple industries are feeling it. The customer success function is not immune. We are hearing more and more that people are questioning whether startups are committed to investing in customer success, and that it may make more sense to shift our customer success careers into larger companies. The question is valid, but the answer is not so obvious. 

Maranda Dziekonski, Vice President of Customer Success & People Operations at Swiftly and Irene Lefton, Customer Success Executive, co-chair of the Customer Success Leadership network (CSLN) and startup advisor, discussed this question with a group of customer success professionals on a live Zoom meeting in a recent session, part of a series of ongoing CSLN weekly helpline sessions.

Question: Should I change my career trajectory and transition from the wild west of startup life to a more established and stable life of a large technology company? If so, how can I do that?  

The best advice I’ve heard in a long time on this subject came from this session.  When evaluating a career change, or rather a change from working at small companies to large companies, be honest with yourself about who you are. This is important because working at a large company is much different than working at a startup. 


Not better.

Not worse. 


Irene goes on to say that at a large company, you will be much more specialized. You will no longer make the rules or be as influential or get to easily help out across numerous areas. Your job and responsibilities will be much more defined. You will be, as they say in Hollywood, “type-cast.” If you are a Customer Success Manager at a large company, but you used to be a VP of Customer Success at a startup or even a Marketing Manager at a startup, no one at a large company will know or care. They will know you only as a Customer Success Manager. 

Something else to consider. Because of being more specialized, you will have less variety in your work at a large company. Irene reminds us, “Just understand yourself. Go in with full knowledge of yourself and what you want”.  

The good news about life being more specialized and defined is that the job will likely be more organized and feel more mature. Processes are in place, reports are defined, and even though the customer success team will always strive to improve, there is a sense that the company knows what it wants to accomplish with customers. This maturity and organization does provide a sense of stability in the work. 

On the subject of moving to a large company because of the sense of stability, Maranda added that large companies are not necessarily more stable. It’s true that startups are riskier. They fail often. They get acquired and people get laid off. But at a large company, you can be more of a number. It can actually be easier for large companies to let people go. To downsize. To restructure. To absorb more work with smaller teams because often teams grow to become too big. 

Maranda reminds us to just be aware of that. 

“The bottom line,” says Maranda, “If you are making this change [to a large company] because of stability, you might want to go back to the drawing board.” There might be other (better) reasons to work at large companies: specialized roles, more training, mentorship, comprehensive benefits, etc. 

Finally, when you’ve decided you’d prefer to work for a large company, consider changing how you present your resume. Irene suggests, “Don’t sell your broad, influential, builder, startup experience. Sell your specialized customer success skills that match the skills required on the job description.” It’s important to match your resume with the language of the job description. Large companies are more likely to look for specialized skills. 


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