Please introduce yourself. 

My name is Kenny Liao, and I’m the Director of Retention & Experience on the Supply Team at Wonolo. We’re known internally as the REx team, and I’m located in the San Francisco office. My team leads Wonolo’s efforts to improve the experience for all the in-demand workers that find work on the Wonolo platform. We do this through the implementation of things like Flex Time Off, portable health benefits, recognition campaigns, skill pathing, and a variety of other perks, programs, and policies.

What events in your life have brought you to your current role today?

I graduated from The University of Texas (hook’em!) and started out my career in consulting with the Boston Consulting Group. However, I’ve always had a passion for marketplace technologies. Early in the days of TaskRabbit, I picked up random delivery, rishesharing, and tech-related gigs, and I also did some driving on Sidecar, Lyft, and Uber during grad school at UCLA. After grad school, I got a job with a marketplace startup called Shift, and I’ve primarily worked at mobility-related startups since, spending time at companies like Uber, Chariot, and Cargo. However, I always felt like these marketplace companies could do more to truly help the underserved workers that flocked to them for gig work, so when I learned about this role at Wonolo and heard how committed leadership was to improving the lives of 1099 workers, I knew it was the right place for me.

When you have to make a difficult decision, what do you lean on?

When making a difficult decision, I lean on three things: 1) the information I have available, 2) other stakeholders in the decision, and 3) my gut instinct. At the end of the day, it’s better to commit to a decision and move forward with it; dragging out a painful decision-making process can paralyze a team, and you often won’t know whether there is a “right” or “wrong” answer until much further down the road. I ultimately have to trust my gut instinct after processing the information available and the thoughts of other stakeholders, and then continue to learn from any poor decisions that were made.

What is one life advice you can give to anyone?

My life advice is to optimize for your happiness (and if you’re married, the happiness of your family). Sure, you can probably always find a job that pays more money, but what if the cost is your workplace happiness? If you’re not happy with something, life is too short to delay making a change. Also, if you’re earlier in your career, take a calculated risk or two (assuming that’s what will make you happy); the older you get, the more responsibilities you have, and the less likely you’ll be able to make a high-risk, high-reward bet on yourself.

If you really knew me, you would know that… 

Most people know that I love a well-organized spreadsheet. But if you really knew me, you would know that I’m a weird combination of packrat and OCD. I get a kick out of collecting things like ticket stubs, concert posters, sports memorabilia, and more, but I’m a little crazy about cataloging them and keeping everything organized in binders and other protective containers. A few other examples of how my OCD-ness comes out: 1) I organize my shirts by color and match the hanger color to the color of the shirt, 2) I keep business cards of restaurants I’ve eaten at and sort them by date of visit, and 3) I keep all of my physical receipts filed by month and year in boxes and keep them for 5 years (because, you know, in case the IRS decides to audit me).