What Working in a Startup Teach Me Professionally and Personally

Darrel Monty
4 min readDec 21, 2019

Written by a Freshly Graduated Millennial

To work in a well-known and established company or in a start-up company was my first thought after leaving my college life in my 20’s. As the fate would have it, I end up working in a startup in service industry.

This decision was harshly criticised by my parents and friends, who thought that I was gambling to work in a not-so-stable startup company. But I decided to take the position anyway.

I work in a start-up called “YesBoss”, a company that provide a virtual personal assistant to help providing daily, legal, and on-demand needs. It was like “Magic” in the US. I become the client service representative (or CSR for short) and was one of the person in charge to replying these inquiries.

The inquiries ranging from ordering a transportation, food delivery, phone credit top-up, movie tickets, travel tickets, setting a reminder, and even when someone vent their frustration. Sounds simple, right?

It was not. All of the above inquiries are difficult since you’re ordering them for someone else and you have a time limit to do so, with a little room for error or sometimes not at all. But it taught me soft skills and hard skills to tackled real world. Being work in a service industry also helps you to understand people.

Here’s what working in YesBoss as a CSR brings me:

1. Knowledge of startups and what they does.

YesBoss was partnering with various other startup and as their client service representative, I need to have the knowledge of partners’ products and how to execute them, and to handle things when they gone bad. This provides me with information such as how to use these apps, that might be useful to me should the situation need it since it is a startup nature to “disrupt” things.

2. Respects of people’s unique personality.

Every person has different perspective, personalities, approach to problems, behaviors, the lists goes on. Many YesBoss’ clients had these traits and I’ve encountered every kind of person available, from a good ones to the scam and annoying ones as well. With my team’s help, I was able to overcame this kind of challenges and learn something new in the process about interpersonal communication. This also applicable in my office as well, since all of them also possess different behavior, interpersonal skills, and problems.

3. Education helps, but it’s not a game changer.

I have a bachelor degree in communication, which should provide me with an edge over my teammates who only hold high school, vocational school, or associate degree. However, I have been bested several times by those who actually have a lower education grade than mine. Even though I was always consistently stays as top 10 CSR officer for a straight 6 month and considered one of the best CSR, I was never in number 1 spot. It was they who actually hold vocational and associate degree does. Higher education helps you get your things done, but it was your work ethic and personality that counts.

4. Honing my soft skills.

CSR is a unique blend of service, sales, secretary, and consultant function. Freshly graduated with little to no practical skills, I need to learn all of these function as part of my job description. It was worth the effort though, I am now able to deliver service excellence to provide good customers’ experience, selling skills to achieve GMV, secretary skills that enhanced my attention to detail, and consultancy skills to increase my problem solving skills. All in one position: CSR.

5. Humility.

I was one of those ambitious young man with ego all over my head, ready to take on any challenges. CSR backgrounds did not require you to have a university degree at all, even some of us only hold senior high school. Knowing that, I feel superior and like I was being cheated, that I deserved better position and payment. However just like I said in point 3 where I was bested by those who only hold vocational and associate degree, I feel that I was thinking too high of myself and I started to think more about respecting and being humble. In work education provide you with skills but without humility to complete it, it will get you nowhere.

6. Future and retirement planning.

YesBoss laid off most of it’s employees at September 30th 2016, including myself. More than half of them are without university degree and prove to be a hindrance when applying for new jobs. Most of them are also over 30’s and already have families, which means they are desperately need jobs ASAP. When I saw this, I knew that not only I need to further increase my qualifications and skills, but also I better be ready with savings, emergency funds, and various source of income to prepare these kind of situation. I also considered taking master degree as well as many executive education, since I’m also interested to have careers as a lecturer or a business coach.

These are what I learned in my old company, which was pivoting and I got laid off as a result. I have a new position now and I hope everything that I learned will be of use in this new position.

This article was first published on LinkedIn on October 30th 2016. Thank you for spending your time to read this. Cheers!

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Darrel Monty

A virgo guy who currently writing to go outside of the box and get useful insights and perceptions