Meet a Happiness Engineer: Ben Chilcote

Have you ever wondered what it’s like to be a Happiness Engineer? Can you really turn customer support into a career? We interviewed Ben Chilcote, a Happiness Engineer based in Dayton, Ohio (USA) who has been at Automattic for seven years to find out more about his experience helping customers with WordPress.com.

Q: Do you recall how you first heard about the job, and then what inspired you to apply?

I was doing websites for fun on the side so I began investigating the idea of freelancing in order to supplement my part-time hours. This exploration lead to discovering the podcast “Your Website Engineer”. The podcast host, Dustin Hartzler, mentioned working for a company called Automattic. It turned out that Dustin lived only a few miles from me at the time. He was gracious enough to meet with me and allow me to pick his brain about the job and the company.

In addition to this, around the same time, I went to a wedding where I was introduced to a friend of a friend who also works at Automattic. To make a long story short, these two happenings prompted me to check out the Happiness Engineer position which seemed to be a perfect fit for me.  A few weeks later I applied, and within a few months, I was in the Happiness Engineer trial. 

Q: Let’s focus on the post-trial period. Once you started working full-time, was there anything that surprised you about the job?

I recall feeling at home fairly quickly. Communicating solely through text was interesting, but was also comfortable for me. I felt like I was surrounded by a lot of people who were like me.  

There was a lot to learn and everyone kept talking about “the chaos” – and they were right. There was a lot to read and a lot to learn. Even so, everyone was patient. There was not a lot of pressure to be up and running quickly. I had a lot of space to take it all in.

I also remember feeling hesitant and a bit timid in this new work landscape. I found that there were a lot of freedoms given – autonomy, flexible schedule, leeway in how to approach and solve problems for users. Having that type of trust and freedom takes getting used to as you may not have as much experience or confidence in yourself. You constantly ask – “Am I doing this right?”. But over time, you do gain the confidence and learn that it is ok to make mistakes and learn from them.

Q: The daily tasks for a Happiness Engineer can vary a lot, depending on the division you’re in and which projects your contributing to. Could you share briefly what your work-day is like doing customer support exclusively for WordPress.com?

Generally, I start my day early, at 7 AM. I do work mostly weekdays, but all Happiness Engineers work two weekend days a month, so some weeks I work on Saturday and take off a weekday. I’m not in a guild or working on a project at the moment so all of my work is 100% centered on providing direct support to our customers. Like most people on my team, I have six hours of direct support work, either in live chat or email (tickets). The rest of my day is spent working on follow-ups, reporting bugs, attending team meetings or one on one’s with my team lead. I also take time to learn more about an area of our product. For example, I’m currently going through a course on CSS.

Q: Looking back at your seven years of experience, if you give your past self advice about being a Happiness Engineer, what would it be?

I would say that one of my biggest stumbling blocks has been imposter syndrome – having the feeling that I don’t belong here, or was hired by mistake. This still does come up time to time, but for the most part, I’m now very confident in what I’m doing. So, if I were to give my past self advice, I would affirm that I am qualified – that I have the skills and temperament, and am well suited for this type of work.

Happiness Engineers come in all shapes and sizes, and from all types of backgrounds. We have skills in all types of areas. But, what we all seem to have in common is the desire to help people, resourcefulness in finding answers, the love of learning, and empathy.

Q:  You’ve been working from home for a while now. Is your lifestyle different compared to what it would be in a typical office job?

I have never really had a typical “office” 9-5 type of job so I don’t have much to compare this to. But I can say for sure that I cannot imagine ever wanting to have one. I have 4 kids and my wife home-schools 3 of them. We are all at home together most of the time. Being able to have the flexibility to walk across the house to take a short break and see what they are up to is something that would be very hard to trade. For a family like ours, having this flexibility and proximity has been a huge benefit.

I know there are people who do need that space between work and home, and working from home can be tricky at times when both work and family are pulling for your attention at the same time – in the same space.  But that is something you can learn to manage.

Q:  What is your one piece of advice for someone who wants to be a Happiness Engineer?

My advice for someone interested in becoming an HE is to ask yourself if 1.) You love helping people, and 2.) You love learning new things. This is what we do day in and day out. Our product is ever-changing, the internet landscape is ever-changing. What stays the same is that we are helping people day in and day out to succeed in whatever they are creating with our products.


Interested in becoming a Happiness Engineer at Automattic? Visit the Work with Us page to learn more about how you can apply!

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