dteam: dote’s Lead iOS Engineer on Being Scared and Taking Leaps

If you feel prepared for your next challenge, it’s not a big enough challenge, says Ivy Xing.

dteam: dote’s Lead iOS Engineer on Being Scared and Taking Leaps

Welcome to dteam, a series on the crown where we introduce you to members of the dote team to highlight the perspectives of the people who work behind the scenes to make dote a great product for our community. In the post below, dote’s Lead iOS Engineer, Ivy Xing, shares her story of joining dote. She outlines what made it an intimidating career leap and why two years in, she views it as one of the most positively transformational decisions of her life.    

After spending two years as an iOS engineer at Edmodo, an educational technology company, I was ready for my next professional challenge. I started to line up meetings with companies I found interesting and dote was the first one I interviewed with. Before hopping on a call with dote’s CTO, who was soon departing for maternity leave, I played around with the app. From the beginning, I appreciated the complexity of all the features of the app.

During my first interview, I learned that dote’s CTO was solely responsible for the app and the entire company was made up of a core team of nine people. I paused. With so many features and complexities in the app, such a small team was surprising to me. As feelings of disbelief balanced with admiration started to subside, I pressed on to learn more about the opportunity with caution. Was I interviewing for a role that could land me in a position of being in over my head?

I asked about the role’s responsibilities. dote’s CTO told me they were looking for one person to own the entire app, just like she’d been doing for some time. This is when I started to really doubt myself. My internal dialogue went something like this:  

I’m two years into my career. My current job is the first full time position I’ve had since college. I have 2 mentors who held my hand until I completed the transition from a noob college grad to a self-sufficient engineer. How can I possibly be the solo frontend engineer for the core platform of an entire company?

I loved the product and much enjoyed our conversation, but I did not feel ready to be who they were looking for at this stage of my career. I tried to end the conversation with the intent of following up later via email to remove myself as a candidate, but was met with a scheduling request to meet more people on the team. I decided to go for it. Worst case, it was just more interview practice, right?

I asked a bit more about the team and learned that dote is more than 50 percent female, with two female co-founders, and a leadership team made up almost entirely of women. For those who are unaware, this is unheard of in the male-dominated startup scene in Silicon Valley. Although I still had doubts about whether this was the right opportunity for me, I was now more intrigued than ever.

Two days later, I arrived at the dote office for a full day of interviews. I met with many members of the team, from engineers and designers, to company leaders. Hours of conversations with the team showed me a wide array of experience and personalities. I was particularly impressed with how dote’s Founder and CEO, Lauren Farleigh, had built an entire company from zero.

Slowly, what started as anxiety, started to turn into excitement as I imagined all the ways I could rewrite the core user experience. The energy and passion from such a talented team sparked something deep within me.

After my last interview for the day, I sat in a conference room trying to juggle everything I was feeling: excitement and trepidation. The door opened, dote’s CTO came into the room, and made me an offer. It was clear she was hoping for me to give an answer on the spot, but said she could give me a few days as needed. Again, my internal dialogue started to breed doubt within me.

In a moment, what I thought was interview practice became a formal offer with real numbers. What were hesitations about hypotheticals suddenly transformed into actual decisions with real stakes. While I loved the team and understood the urgency of the situation, it was a significant and almost unfathomable career move for me. I bid my time on the offer.

Modcloth dress2

In the next few days, I squeezed in three onsite interviews with other companies and was fortunate enough to receive offers from all of them. One of the offers came from what I’d decided was my top choice at the beginning of my job search. It was what one could call the safe choice. The first engineer I spoke with was a world class architect who I admired and the other team members I met were just the kind of mentors I was looking for. With great resources and growth opportunities, the company was a natural next move from my current job. I envisioned a clear path of success—I knew exactly what my role would be and how to shine in it.

And yet, I couldn’t stop thinking about how I felt with the team at dote. In fact, the more I interviewed, the more the sameness of other companies proved how unique the dote opportunity was. The diversity in gender, ethnicity, and backgrounds combined with the passion and drive of the team were not things on an equal playing field with mentorship.

The spark I felt on the day of my interviews at dote stayed with me. It was a spark of passion to build something great with an entire team on the same shaky boat. It was a spark of longing to take unthinkable risks regardless of what made sense to the rest of the world. I closed my eyes to envision my path at dote. There would be so much responsibility expected of me with no one else’s plans to rely on. As I tried to envision a path of taking on the challenges, I couldn’t even imagine what the specific challenges would be. I was scared.

I decided to think about the last time I made such a difficult decision, which brought me back to when I chose what college I went to. I turned down Berkeley for Bowdoin to pursue Math and Computer Science. If you haven’t heard of Bowdoin, then you know what made this a tough decision. Choosing which college to attend felt like a relevant comparison because of how important and difficult it was. When I landed on Bowdoin, everyone thought I was out of my mind, but I knew deep down it was what was best for me.

My four years at Bowdoin were the best time of my life. I saw tremendous intellectual and personal growth. I know I would make that same decision a thousand times over. I started to think, any time you take a leap, it’s going to make you feel a little crazy, right? Deep down I started to feel like dote was “the Bowdoin” for me—the less obvious yet right decision.

With reborn enthusiasm, I started to gather as much information as possible. I talked with dote’s investors and met with leadership a few more times. I learned that startups battle uncertainty every day to achieve miraculous heights, and dote wouldn’t have gotten this far without conquering the fear of failure time after time. I learned that while I may not have entirely believed in myself, dote believed in me, and that’s what mattered.

The more I learned about the company and culture, the more I was attracted to the passion of the team, the promise of the company, and the extraordinary potential for personal and career growth at dote. The only thing stopping me was what I saw as my own limitations.

Even then, how could I let my own thoughts limit my future? The spark within me grew too strong to leave any regrets. I wanted a decision that I could look back on and say, I would make that same decision a thousand times over. Many companies have great mentors, resources, and enticing compensation, but every team is different. What is uniquely crazy and uncertain is sometimes exactly what would be worth building. I knew that at dote I couldn’t just survive, I would have to fight to thrive. So, I lit the spark of passion and took the leap.

I accepted the offer and had one week to learn about the codebase before dote’s CTO left for maternity leave. I was terrified, but I started the journey anyway, quickly learning how to keep going even when I was scared. I would proceed to rewrite most of the codebase, build an endless stream of complex features, and learn a multitude of communication and leadership skills over the next 2 years, which brings me to where I am today.

It was a journey of tremendous personal and career growth. And I’m now more sure than ever that joining dote is one of the best decisions I’ve ever made that’s changed my life for the better. Looking back, I’m proud that I listened to the voice inside of me that encouraged me to take the leap. After all, if you feel fully prepared for your next challenge, it’s probably not a big enough challenge to begin with.