The interview

I landed my first job interview at a start-up in San Francisco in 2014. I had been working at an insurance broker at the time, and when I heard about the up and coming space of “insurtech”, I immediately knew I wanted in. After a bit of research, I found a company that was “disrupting the insurance space” and applied for an entry level role. Just a few days later I walked into what would be one of the most important job interviews of my career.

The interview was going great when I had my final round with one of the VPs at the company. During the interview, she asked me to tell her what I had learned about employee benefits while at my current company. Confidently, I explained a project that I had worked on which taught me all about FSAs and HSAs (or so I thought). She listened carefully and then hit me with a very specific question about FSAs, asking: “If my FSA plan starts on January 1st and I needed to use all of the money allocated on January 2nd, could I?” I didn’t know. I got very nervous and tried to come up with something before finally admitting, “I don’t know”. We moved on with the interview. When it was over, they told me “we will follow up with you” and I left feeling defeated.

When I got home, I couldn’t stop thinking about her question. I decided to do some research, and it didn’t take me long before I found the correct answer and knew I needed to follow up. I asked the recruiter if I could have the email addresses of my interviewers so I could send them thank you notes. When writing my thank you note to this specific interviewer, I added an extra paragraph with the answer to her question. She never replied but I felt proud of my email.

The next day, I ended up getting a call back and was offered the job. I was stunned and couldn’t accept their offer quickly enough. On my first day, I ran into the VP who interviewed me and nervously said hello. She said “thanks for the email” and gave me a smile. It took a few months before I finally had the courage to ask her about the interview. She told me that my follow up email confirmed her decision to hire me. This was my first lesson on embracing the unknown and one that would help shape my career in pivotal ways.

First week on the job

During my first week as a customer service agent, I was handed an iPhone which answered our customer support line. I was given a brief overview of how it all worked and then my manager left - it was just me and the phone. A few minutes later, the phone rang. I answered the call, listened to the customer’s question, and didn’t know the answer. The feeling was familiar; but this time, I took a different approach. I asked the customer if I could have a few minutes to look into their question (to which they happily agreed) and put them on a brief hold. I resourced internally until I had the correct response, got back on the phone, and provided them the information. Their appreciation fulfilled me.

My interview experience helped me understand a few important things:

• People don’t expect you to know everything

• People understand when you admit you don’t know something

• People appreciate a thorough and timely follow up

When I came to realize the above, I was truly able to embrace the unknown on the other end of that phone line. I soon became exhilarated every time the phone rang and took every opportunity to learn more and build trust with our customers. I became a relentless advocate for our customers - breaking down walls (professionally and reasonably, of course) to get them answers. I wasn’t afraid to ask questions and soaked up every ounce of knowledge that was coming my way. I embraced it and I loved it. I started realizing that every time I didn’t know the answer was an opportunity for me to learn, grow, and become a more valuable asset to this company. Instead of being defeated by the constant not knowing, I developed the courage to face it.

Of course, customer service is hard – there are many moments of frustration, feeling defeated, and dealing with some very unpleasant customers. However, as soon as I molded my mindset to be open and fearless towards what might be coming my way, I was able to find passion and purpose in my career that opened more doors than I ever thought possible.

Growing in my career

This mindset and curiosity to learn was crucial as I grew into management. My team became my customer and my day was filled with questions and problems that I didn’t know how to answer. I embraced this with the same eagerness and resilience that I had learned over the years and became their biggest advocate and resource.

As I started bringing on new team members, I would often sense their frustration and sense of defeat within those first few weeks as they stepped into their new customer-facing roles.

I always give three powerful pieces of advice from my own learnings over the years:

Embrace the unknown

Be humble and brave to admit you don’t know. Be open minded and have the courage to ask questions. Realize that your most important growth will come from new situations that arise and how you handle them.

Own your follow through

Let go of trying to control the other end of that phone line and focus on controlling your reaction to the situation. Be attentive, timely, and thorough in your follow up and do work that you can feel proud of.

Allocate time to reflect on your growth

Dedicate time to realizing your growth. Your days will only continue to be filled with not knowing but don’t let that get in the way of recognizing your milestones and how far you’ve come along the way.

I have found that this advice can truly help individuals get over those initial hurdles and help them find their own excitement, passion, and purpose in the hard work they do every day.

Joining Shepherd

About 4 months ago, Justin (our CEO) approached me about joining Shepherd to help build out the customer experience organization. The role entailed building and executing a customer experience strategy that would help change the way commercial contractors feel about their insurance providers - this was big. My mind immediately flooded with all the things I wouldn’t know how to do (and I’ll admit, I was nervous). However, as I took the time to get to know the team and mission, I knew I wanted in.

This became a crucial moment for me to take my own advice. This was a moment for me to truly embrace what was coming my way - with excitement, curiosity, and resilience. It was a time to reflect on everything I had learned over the years that led me to this point and have the confidence that I can help build and lead this team with success. So, I accepted the role.

As I begin my journey here at Shepherd, I couldn’t be more grateful for that first interview experience I had over 8 years ago that helped prepare me for this exact moment. In a few short months, my days have been filled with endless energy and inspiration as I work with an incredible team who is trying to make a true impact - and I’m ready to take on whatever is about to come our way.