How to Transition Into Customer Success

Diana De Jesus
Customer Success Manager

Interview Highlights:

  • If you don’t have the relevant experience to land a job, create your own.
  • Creating content is a great way for recruiters to find and approach you. 
  • It’s not the size of your network that counts, it’s how much value you bring to it (and how much value they bring you).

Can you please introduce yourself and what you do for Catalyst?

I’m Diana De Jesus, full-time mom, CEO of my house, content creator, and Customer Success Manager at Catalyst.

What were you doing before you got into CS?

I did a number of things before going into Customer Success. I worked at a law firm straight out of college and stayed there for two years, and then spent some time in the restaurant industry. 

When I became a mom, my husband and I started a property preservation company. This was right after the housing crisis, so there were a lot of “zombie homes,” and plenty of work to do. But what that really meant was I stayed at home doing a lot of paperwork while he did the fun stuff - fixing up the houses. 

I created a website for our business but it was so plain! I wanted to make some tweaks, so I started tinkering with HTML and CSS. That’s when I discovered coding and was immediately drawn to tech. 

I joined a local tech community and found my first tech role, which was an internship as a mobile app developer. I was there for three months, and also blogged on the side about my learnings and all the different programs I was using. I landed my first “customer success” job that way. 

Why didn’t you consider it to be truly customer success?

It wasn’t Customer Success for a number of reasons. The job had some elements of CS, but it definitely wasn’t how we define CS now. 

There was a bit of onboarding and conversations around renewal, but it wasn’t a structured way of looking at the post-purchase journey. It was ad hoc and about 50% Customer Support. I was still madly in love with the technical side so I transitioned to a technical Support role in the same organization. I had the opportunity to dig more into my technical things like HTML, CSS and JavaScript and I also built the Support team from the ground up. That included hiring the team, building the resources, and structuring the team.

When did you discover you liked Customer Success better than Technical Support?

I took a Reforge course back in the Fall of 2018 on adoption and expansion. The reality is that the course wasn’t really meant for someone in a Support role, but my company at the time had an initiative around churn reduction so there I was :) 

By the time I finished the course, I was madly in love with the idea of retention. I wondered, “How can I do that? How can I help with retention?”

So I looked at roles like Product Marketing Manager and Growth Manager among others  until I finally stumbled on Customer Success. I loved the idea of having so much influence on helping a customer get the most value out of a tool/service and stick around.

And did you get the first CS job you applied to, or did you have to go through several applications?

The first CS job I applied to was a disaster. At that moment, I wish I was cool enough to play it all off like I had a wifi problem and just end it prematurely. That entire experience still gives me nightmares. 

I didn’t know any of the things that were asked of me in that interview. That’s when I realized I had a long way to go to learn about Customer Success. I had to go through so many interviews to land a job.

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How did you make yourself a more attractive CS candidate?

When I was in the pits, I explained my situation to some friends from marketing. I told them how I couldn’t get a job in CS because I didn’t have the experience, yet didn’t have a way to get the experience that I needed. 

Then they said something that blew my mind. They told me to create my own experience. When I looked around, I realized that that was exactly what they had done. They created podcasts and had guests talk about their experiences, and in so doing absorbed it and made it their own. 

I knew that’s what I had to do, too. I started putting out lots of content; I wrote a ridiculously long blog post about Nir Eyal’s book Hooked among other things. I learned what made people decide to buy, what makes them return to a product, and more.  

As I wrote these massive blog articles, I realized just how much I love writing. So I came up with the idea of recapping podcast episodes. As a mom, I don’t have 45 minutes to an hour to listen to a podcast episode, but I do have five minutes to read a quick article. 

So I started Keep the Customer, which was a blog that recapped podcast episodes by CS professionals. As I did this, I gained the experiences of the people I was listening to and then used that knowledge when I interviewed for CS roles. 

The best part? It worked! I got the job I wanted!

Do you recommend other job hunters follow the same path?

You don’t have to follow in my exact footsteps, but I do recommend creating content. There was one consistent thread throughout my entire career - I always created content before I did something big. 

I started that blog about learning how to code, I created Keep the Customer (which is how I got this job at Catalyst), and I created the Open Book of Customer Success with my friend Elizabeth Cortland, which was over 200 CS resources in one place. 

Creating content is a great way to create conversation pieces, and is also a way for recruiters to find you and help you lock in that job. 

What kind of person would work best in CS?

Curious people do well in Customer Success. 

I’m not the only one who thinks this way. I was on a panel the other day, and two separate CS leaders that are actively hiring said the same thing. When you get on these customer calls, you have to dive deep into what they need. You don’t just go with the high-level answer. 

This can be seen during job interviews. If you’re curious in the job interview and ask a lot of questions, then you’re going to be curious with your customer. 

Empathy is another important quality for customer success. You want to put yourself in your customer’s shoes so that you can be an effective champion for the customer during internal conversations - like with product, for example. 

Let’s talk about resumes and cover letters. What was your process for building them?

I don’t miss those days at all. There are many articles out there that talk about cover letters and resumes and they do it better than I can.

What I can say, however, is that having referrals makes a difference. I recently wrote an article about the three mistakes I made while I was looking for a job, and one of those mistakes was not having referrals. 

I found this little graphic that said 7% of all applications coming in are from referrals, and yet of the 7%, 40% account for the jobs that are actually filled. That blew my mind!

It’s not about the cover letter and the resume anymore. You are the cover letter and resume. You have to be your own walking billboard. That’s why I place such a big emphasis on branding. You have to go out and talk to people. 

Now, when I say talk to people, I don’t mean reach out to a hiring manager and say, “Hey, I need that job!” You gotta go in there and court them a little bit. You need to attend the events and chat with them at the event. Start building that relationship until you get to the application process. It’s a very long-term strategy. 

If you don’t have a personal network, start going to events and joining communities. Find people and talk to them. Go online and find the people you want to work for. Comment on people’s posts and start the conversation from there. It’s not the size of your network; it’s what you end up using your network for. 

Slide into their DMs with value. People love getting words of affirmation, so go in there and tell them you saw their post, heard their podcast, or read that article that they wrote and you loved it. Don’t lie about it, of course. You have to actually read and like the content they put out. 

What would you do differently if you had to do it all over?

The first thing I would do is narrow down my search. We all fall into this trap where you’re so desperate for a job you basically take anything. And the reality is, that doesn’t work. You’ll do something for a couple of months, and then finally admit it was a mistake and look for something else. And the cycle begins again.  

You have to narrow down the search based on your desired goals. What size company do you want to work for? Do you want to work for a startup? A bootstrap company? A corporate place? And so on. 

Customer Success is so vast. There’s CS pretty much everywhere in every industry. So deciding what you want to do and the place where you want to work is the first thing I would do if I had to do it again. 

Another thing I would’ve done is find a mentor. I could’ve moved a lot faster if I actually had someone that I could discuss my problems with. I had to be scrappy and figure it out myself, but if I had someone in my corner helping me out, things would’ve moved a lot faster.

Do you have any last-minute messages for our readers?

Once you finally get to the other side and become a Customer Success manager, you have to remember that there will be a learning curve and there are a lot of skills you’ll have to develop. 

You’re not going to be able to build those skills overnight. It takes a long time. It’ll feel all over the place at first, but it’s worth it. Customer Success is a great career path, it just takes patience and time to get in there and learn the ropes.


Catalyst is the world's most intuitive Customer Success Platform (CSP), built by an experienced group of industry leaders. Previously, our founder built an effective Customer Success organization for one of the fastest growing cloud companies in the world. Catalyst integrates with all the tools you’re already using to provide one centralized view of customer data. Customer Success Managers can proactively take the right actions to prevent churn, such as receiving automated alerts when a customer is not using certain features that are critical to their success.

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