How I Jumped From Hospitality to Customer Success

Tiana Crosbie
Customer Success Agent
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Interview Highlights:

  • Don’t let your self-doubt block your way forward
  • Focus on promoting your transferable skills
  • When filling out an application, put yourself in the hiring managers shoes

Can you please introduce yourself and what you do?

I’m Tiana Crosbie, and I’m working in the financial tech industry as a bilingual customer success agent for KOHO Financial Inc.

What was your early career like, and how did you get into CS?

My early career consisted of quite a few years in customer-facing environments. Most of them were varied enough to be challenging every time I entered the new environment, so I had the opportunity to increase my skills in a few different fields like retail, administration, hospitality, food and beverage, and even sales. 

Because of this variety of sectors, I gained insight into the different kinds of clientele that you can come across and was able to learn how to build rapport with each of them in my different roles. This worked with both international and local clientele, as well as budget-conscious versus luxury clientele. And this experience translates very well into CS. 

What attracted you to your current position?

Being able to interact with users and customers through a different lens than what I’d become accustomed to in my previous customer-facing roles. I was really in awe of the concept of being proactive. Customer service tends to be more reactive.

One other aspect that attracted me was how I was empowered to follow up with people about the concerns or inquiries that they brought forward, and having the ability to build rapport with them even further through that follow-up. My past roles weren’t really customer-centered--not in the way that CS is. 

What challenges did you face job hunting?

There’s smaller ones, and there’s bigger ones. 

One of the smaller challenges was when I would look at a job application for a CS role, the post asked for experience with ZenDesk or some other real-time messaging system or software tool. I had not had as much experience in tech as other candidates, so that was a bit daunting. I created a bit of internal uncertainty for myself. 

And on that point, the work industry that I had been in so far were always with very well-established companies with thousands of employees. Quite a few of the CS roles I was seeing were with startups and scale-ups. It was a smaller work environment that I was accustomed to, which was also a bit daunting. 

Looking back now, I can see that my limitations were mostly self-imposed. It wasn’t the CS role itself that was difficult--rather, it was my uncertainty. 

One real challenge though was that because I had been in hospitality for so long, most of my network worked in the same field. This was a gap in my network that I felt as I tried to introduce myself into the tech world. 

My limiting self-belief really was the biggest challenge. I was having a lot of trouble getting past the mental hurdle of not ever having been in tech or customer success before. I had a massive amount of transferable skills, but I suffered from impostor syndrome.

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How did you overcome those mental hurdles?

I relied on my support system. Specifically friends and family, and chatting with people that had also made a big career change but were initially uncertain about their pivot. 

Hearing that from other people, I was like, “oh my gosh, that’s exactly what’s going on for me, too!”

It was nice to have that reassurance and that I wasn’t alone. 

Which transferable skills or traits carried over to what you’re doing now?

Embracing a sense of urgency when it comes to certain work tasks and responsibilities. Being aware of how time-sensitive certain inquiries or concerns can be helps me tackle them at faster pace.

Being flexible and adaptable. Recognizing when the path you had assumed to be the right one is not actually going to be beneficial for the customer. How to make that change gracefully is very important for getting the problem solved.

A big one is empathy. That comes naturally to me, and I’m able to use it at work in a genuine way. 

Persistence and resilience, for sure. Hospitality industry hours are insane. The clientele can be very demanding depending on what environment you’re in. 

An understanding of the conflict resolution process and how it can come full circle. An angry customer can leave more loyal to the company than before if you’re able to prove that you care and that you’ll be with them along the way. 

What do you think helped you stand out as a CS candidate?

My bilingualism really helped increase the amount of roles that I was eligible for. That was a godsend. 

But I think people that may not have the advantage of being fluent in a second language can benefit from learning about how I approached my cover letter. I ripped my old one to shreds and rebuilt it from scratch. 

Instead of the usual format where you say a blurb about yourself and then end with “looking forward to hearing from you,” I took a different approach. 

I took the job description for the role that I was interested in. And then I went through my resume and cover letter and reviewed them based on their needs. “Oh, they want someone with experience in different kinds of software. I did that when I worked as a front desk agent and had to learn different booking and messaging systems.”

So just being able to link what they were looking for and what I had experience with in the past was super valuable. Not only to help me get rid of that impostor syndrome, but also for the hiring manager and employer to look past my lack of CS experience, and to see all of my transferable skills. 

What advice would you give to candidates who want to jump careers?

In general, you need to take the time and think about what you would bring to the table that not only comes naturally to you, but others may not be able to do as effectively or consistently. An example that comes to mind is that I’m naturally positive and enthusiastic. I am energized by social interaction and I gravitate towards it. So I just need to bring the best version of myself to the interaction. 

In CS, my days are filled with people chatting or calling in with feelings of confusion about a feature or a product, or they have a concern or an issue they’re facing. I’m constantly able to utilize my positivity and remain upbeat throughout the entire interaction and resolution process because I’m optimistic about the outcome. Even when people express anger, I recognize that their anger doesn’t sit with me; it sits with the obstacle that they’re facing. 

So I think that differentiation and playing to your strengths are key. But of course, you want to make sure that the special “something” that comes naturally to you is related to the field you want to enter. 

For specific roles, you have to put yourself in the hiring manager’s shoes and pay attention to how they list the responsibilities of the position--which ones say preferred or optional. Find what they really want and wrack your brain for any related incidents you’ve been in that can showcase your work ethic and positive traits.


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