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How Long Does it Take To Transition To Customer Success?

Updated: Jan 23

I often get the question:

“How long does it take to transition to a Customer Success job?”

And at the risk of sounding vague, my answer is always the same: It depends.

Every scenario is different. Things like experience, networking skills, and effort will influence your timeline significantly, which is why there is no clear timeline.

However, some things are within your control to help you advance your transition. After speaking with hundreds of people looking to make the switch over to CS, I’ve seen just about everything. The mistakes that cost people interviews to the strategies implemented to secure the bag.

In this post, I’m going to share with you the four things you can do to get closer to landing the job. Let’s get into it 👇

Get Clear On Your Game Plan

If this sounds familiar, it’s because I’ve beaten this drum before (several times). If you don’t know what you’re looking for, it’s challenging to find it. Whatever “it” is.

That’s like looking for someone in Central Park in the middle of August, but you don’t know who that “someone” is.


I’ll never forget when I reached out to a friend of mine to say that I was ready for my next move. Their reply was something along the lines of “Great! Tell me exactly what field, company size, and role.” Before then, I hadn’t considered that I was the one in control and that I needed to know what I wanted.

Why is this important? Because when we say we want to work in Customer Success, we’re talking about an entire tech space that within it has a lot of fields, and even within those fields, you’ll find sub-fields and other criteria. The whole thing is like a Russian nesting doll.

But the challenge I see people face is that they don’t even know where to start when searching for this clarity.

My advice is to start with what you already know. If you’re an educator, stick to edtech. If you’re a bartender, stick to tools that are all about customer/user experience. If you’re a real estate agent, lean on property management tech.

You have what’s known as “subject matter expertise,” and that’s very important to these tech companies. Customer Success is still relatively new. There is no Customer Success major in college (except for that one university), so naturally, not every company is hiring veteran CS professionals, and apparently, nor do they all want to.

If you’re starting from scratch, that’s okay too. Think about things you enjoy doing, like maybe you’re super organized, so try Googling “tech companies that help organize.” Sounds silly, but you’ll get some hits back.

After you’ve gotten clear on what you’d like to do in CS, it’s time to take it one step further — doubling down.

Target One Area Only

You have to convince the recruiter that YOU are the right person for the job. If your resume or LinkedIn spotlights five positions, you’re open to like:

  1. Customer Success

  2. Project Management

  3. Scrum Master

  4. Product Manager

  5. UI/UX

You have lost the attention of the recruiter.

These are five different disciplines that surely overlap in some ways, but they are five different jobs.

Tough love moment: You’re not increasing the number of jobs by putting all of these areas on your resume. You’re hurting your chances in each of these fields.

It’s hard to stick to one or two when you’re unsure what to do. But it’ll never do what you think it’s doing. You’re not a one-size-fits-all person.

If you identify with this point, I recommend doing thorough research into each role you have listed on your resume/LinkedIn. Here’s how to do that:

  1. Watch day-in-the-life videos for each role on YouTube to get some insights into what it’s like to do the role

  2. Understand what are the requirements for each role, and assess whether you meet at least the majority of those requirements (or if you’ll need additional learning)

  3. Truly ask yourself if you actually want to do that job

Go The Extra Mile

I don’t want you to burn out, so we’re only going to go the extra mile once we have clarity 😉

I’m not asking you to send your resume on a cake, but we’re going to have to do a little more than just the “spray and pray” method.

Learning the CS basics

Customer Success is hard. There’s a lot of jargon. You have to understand the business-to-business Software as a Service model AND how to work effectively with customers. Some companies provide extensive training that covers these areas.

Your job is to educate yourself as much as possible, and luckily we live in an era where information is everywhere. You can take a quick course on Udemy, watch a YouTube video, read a book, subscribe to a blog, listen to podcasts, attend events, etc.

Full disclosure: it’s going to take some time.

Where do you start?

You have so many options for learning about Customer Success, and A LOT of them are free.

I recommend starting with podcasts. It’s a lot more digestible, and the commitment is low (you can listen to an episode while you’re washing dishes). I recommend the following:

As you’re listening to episodes, some things will go over your head. Keep a doc handy to jot down the words/acronyms and processes that you’re not familiar with. This will serve as your ad-hoc curriculum. If you're looking for a Customer Success Curriculum that's already structured for you, check out this resource.

There are also blogs, books, Customer Success content creators on LinkedIn, and so much more. Do your homework or use this resource to help you get started.

Sidenote: this shouldn’t even be under “going the extra mile.” You can’t wing this! Learning the basics is a MUST.

So now you hopefully know the terms, and have a good understanding of what Customer Success is and what you’d be doing, so you’re likely ready to start applying.

The application process itself can be extensive and, at times, mysterious. That’s why I put together a comprehensive course that walks you through the basics of customer success AND the entire application process. In it, you’ll find a complete overview of prepping for the interview, standing out throughout the interview process, and navigating things like the presentation and salary conversations.

While the guide will steer you in the right direction, I want you also to flex your self-awareness muscles. You will get rejected – It’s part of the journey. But what you do with those rejections will define your success.

Believe In Yourself

I seriously should’ve started with this point.

Hear me out. If you don’t believe in yourself, why should the recruiter and/or hiring managers believe in you? #toughlove

Of course, I know that simply telling you to believe in yourself is easier said than done. I’ve been there before. When the “I’m not good enough” voice starts to take control and “who do I think I am?” gets louder and louder each time.

It takes a lot to silence these negative thoughts – I’m looking at you, therapy – but you can do some things to help build your confidence. We’ve already covered it at length here, so it should come as no surprise: LEARN.

If you want to become unstoppable, replace an hour of scrolling on TikTok #myguitlypleasure with a podcast episode or book. Then, pretend you’re back in school and jot down a quick summary. Ready to take it to the next level? Sign up for a Customer Success event (check out if you’re in a big city). Leave a comment on someone’s LinkedIn post or write your own post on a platform like Medium.

Get out of your comfort zone! You got this, and you just need to challenge yourself.

"Diana, you haven't talked about how long it'll take to break into CS!"

I know. That's because that answer will depend on YOU. Your experience, your background, your level of effort, how well you interview, how polished you come across, the networking you do, how you market yourself, and how you build relationships throughout the interview process.

There's no clear timeline. It took me a solid 6-8 months to make the switch and I was already working at a B2B SaaS company.

If this post is giving off “it’s hard to break into CS,” that’s because it is.

BUT, it’s not impossible.

Many people have made this switch from a wide range of industries (hospitality, medical, education), and I know because I’ve helped them make it happen. Maybe one day, I’ll be highlighting your success story :)


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