December 3, 2019

Career Path: Huan Lai, Director Of Engineering at Hopper

What do the career path and the day-in-the-life look like for a Director of Engineering at Hopper?

We connected with Huan Lai to find out!

Click here for a list of job openings at Hopper, or check out the right side of this page!

Where did you grow up?  What did your parents do for work?  

My parents and I emigrated to the US when I was still a toddler. I grew up in Dorchester, a neighborhood of Boston, MA. My father was a blue-collar worker for a local manufacturing company. My mother was a homemaker, taking care of my three sisters and me.

Where did you go to college?  What did you study and what were some of your initial jobs out of school?

I went to WPI (Worcester Polytechnic Institute) to study Computer Science. I actually started my career during high school, doing an internship at IBM. It was more of a community outreach program, but it made me really interested in software development. My first real job writing code was for a startup in Woonsocket, RI during my Freshman summer and first semester of my Sophomore year. That experience was definitely Type 2 fun. Crazy hours, nights, weekends, only to see the company go under in the end, but that was one of the best learning experiences I could have asked for. I spent the rest of my time in College working for Constant Contact, where they hired me as the designated “young guy” to build out their “Labs” group, a forward technology research team that played around with crazy concepts (in 2009) like mobile apps. 

After college, I had a couple of different jobs as a Software Engineer - I wrote manufacturing optimization software at Vistaprint for a little while, did spam detection SaaS at Acquia for a little while, and did some robotic pathfinding optimization at Kiva Systems (now Amazon Robotics). I switched over to engineering management during my tenure at Amazon, and that leads me to my current role as Director of Engineering (Air) at Hopper.

Huan Lai Hopper

What has attributed to your success thus far and has helped propel you to the position you have now?

I consider myself very lucky to get to where I am today. I was lucky enough to discover something that I love doing (and people are willing to pay me to do it) really early on in my life, which gave me a bit of a head start compared to my peers. And along the way, I stumbled upon a couple of mentors who really took me under their wing and taught me everything I know.

But the thing that I attribute my success to the most is having a passion, not for the destination, but the road to get there. There is a famous Mark Twain quote that I live by: “Find a job you enjoy doing, and you will never have to work a day in your life.” Growing up, I loved building things. Software is one of the lowest barrier-to-entry mediums for instant satisfaction building you can imagine, and I fell in love the moment I got my hands on it. I stumbled into management by accident and quickly discovered that building teams weren’t actually all that different from building software, but also gave me the personal satisfaction of supporting newer engineers and managers and watching them grow.

Can you share the high-level responsibilities of your current position as Director of Engineering at Hopper?

I am responsible for the teams building Hopper’s Flights product. When I joined Hopper 1.5 years ago, the entire engineering organization was around 20 people. Now there are over 30 working on the Flights side of the shop alone, and our rate of growth isn’t slowing down. Much of my job is around figuring out how to scale the people, processes, and technology to not only keep up with the growth, but accelerate it. 

Huan Lai Hopper

Any tips for someone considering a career in Engineering?

If you don’t love what you do, do something else. Our line of work is not easy, and you will run into your fair share of failures along the way. Loving what you do provides that extra push of motivation needed to get across the finish line.

Day in the Life

Coffee, tea, or nothing?

Nothing. I drink a lot of sparkling water, but nothing caffeinated. 

What time do you get into the office? 

Usually around 8:30

What are three things that motivate you in your role?

  • Since last year, revenue is up 4x and conversion is up almost 2x, while the team has grown by 3x and retention is still well above industry averages. The data shows that we’re doing something right, and thinking about the future excites me.
  • The level of responsibility and autonomy that we expect from our engineers and managers is outside of many of their comfort zones (intentionally). Despite this, and probably because of this, they are thriving. Observing the personal growth of the people on my team is one of the most gratifying parts of the gig.

  • Our company's mission is to help everyone discover the planet we live on by making it cheaper and easier to travel. As an avid traveler, this resonates with me.

Every day is different, but can you outline what a typical day looks like for you?

  • I spend a lot of my day in 1on1s. I have weekly 1on1s with all of my direct reports, monthly 1on1s with my skip-level reports, and weekly/bi-weekly 1on1s with many of my stakeholders. 

  • Because of the importance of hiring, I usually spend at least 2 hours a day doing interviews and calls with potential candidates.

  • Because the teams spend a lot of their time focused on their team’s objectives for this quarter, I focus a lot of my time on figuring out roadmaps, and organizational strategy/processes to hit that roadmap for the next quarter.

What time do you head out of the office? 

I try to leave by 5:00 sharp so that I can spend time with my wife and son before bedtime.

Huan Lai Hopper

Do you log back in at night or do you shut it down completely?  

I have Slack on my phone, so I never truly shut down completely. That said, outside of business hours I’m usually in read-only mode. I have a rule to never respond to messages unless it is an emergency, and simply flag messages to respond to the next morning. Between 8:30 am and 9:30 am before my meetings start is a good time to respond to messages.

Any productivity hacks?

There will always be an infinite amount of work. No one will throttle the firehose of work for you. A big part of being successful is learning to say no and hard prioritizing your tasks. You can theoretically work more and more hours, but you’ll eventually burn out and quit. 

What are the 3 apps that you can’t live without?

  • Slack - I always joke that 50% of my job is sending Slack messages

  • Netflix/HBO - I have a 1hr commute on the train each way and streaming keeps me sane

  • Amazon - I hate going to the store, so I buy everything on Amazon. 

What professional accomplishment are you proudest of?

During my time at Amazon, there was an engineer that we were on the fence with during the interview loop and I ultimately decided to take a risk and hire him. He was inexperienced and had a non-traditional background, but was one of the most motivated and passionate people I’ve ever worked with. He eventually grew to my most trusted engineer and stepped up to a team lead role. After I left, he eventually grew into my old position.