Let’s meet Jason!

Hi! I’m Jason, and I’ve been at Wonolo since 2017. My role is the Director of Supply Operations. My team and I are responsible for ensuring that Wonoloers are set up for success from the minute that they enter the Wonolo platform, which includes onboarding, screening, job success, and earning badges that empower them to be able to open themselves up to more opportunities on the platform. In a nutshell, we ensure that Wonoloers are able to find and access the jobs they are interested in, so they are set up to be successful for each and every Requestor they work with.

What are you grateful for today?

I am grateful to be happy, and that might sound cliche but it took me a long time to get here. I have built an amazing career, network, and reputation. I have friends and family all over the world. I am also newly married to my husband Scott. We just celebrated our one year anniversary together! We purchased a home, have two dogs and a lizard. Even though it’s not the most traditional family, I finally feel like I’m exactly who I am and where I need to be. There’s no better feeling than that!

When you were in high school, what did you dream of becoming?

I wanted to be a trauma surgeon following in the footsteps of my grandfather who was an orthopedic surgeon – this quickly changed after my first semester in college. I always said that I would not have a “normal” job and that I would do something different and exciting. Nothing scared me more than having a boring, repetitive, mundane job.

What events in your life have led you to your current role/job today?

For me, being in tech was not a part of my career plan. After my first college semester of being pre-med, I quickly realized that was not the path for me. I switched my major to criminal justice and wanted to be in the Federal Law Enforcement – something like the CIA or FBI.

In 2013 after I moved to San Diego from Ohio, I was in the process to be accepted to work in Homeland Security and the San Diego PD when I got an opportunity to work on a temp project as a contractor at Uber. I had zero experience in tech, operations, or working in a startup. I just found a unique opportunity and a bit of luck with a connection that worked at Uber.

I saw this as an opportunity to get my foot in the door and try something different. Once I started contracting with Uber, I immediately applied for a full-time position in Los Angeles and worked my butt off to prove that I could do it even without having the experience or education to support it. Long story short, I interviewed and was hired full-time to join the local operations team.

I dropped out of both the San Diego PD and the Homeland Security process. At the time it may have seemed a bit crazy as I was taking a big risk to leave something I had worked so hard for, but I really felt strongly that Uber was going to be a once in a lifetime opportunity. I thought, “Well I could always go back to law enforcement if it didn’t work out.” I went on to spend 3 years at Uber working on exciting projects across the U.S. and then running an operation across six countries in Southeast Asia.

Seven years, four startups, and eight countries later, I am here at Wonolo as the Director of Supply Operations and I could not be happier with how my career has developed and changed over time.

When things do not turn out the way you planned, what is the first thing you do?

This is a hard question – for me, it really depends on the situation. For someone who has ADHD, one of the things I have to constantly work and improve on is how I react to certain situations.

For anyone who has or truly knows someone with ADHD, you know it’s not as cut and dry as “having trouble focusing”, “unorganized”, “hyper”, “scattered thoughts”, or any of the other stereotypical things that are associated with someone who has ADD/ADHD. It’s much deeper and complex- just as the individual who has it.

Getting back to the question, I will answer it with what are the things I do when something does not turn out as planned. Usually, (if I am being 100% honest here) I react. I will not try and spin it any other way. I react and then I usually try to take a step back and look at the bigger picture and situation at hand to dissect it. For me, I need to understand why something is not working or not going as planned, so I can reset, reboot and try again. I have learned, and still, am trying to perfect this skill. If I can remove myself from the situation at that moment and take a step back, I will be able to figure it out.

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

My gut is always my go-to. 99% of the time, that inner feeling is right, and I always trust my gut. I never look back and regret a decision because I know that in that specific stage of my life, I did what I felt was right for me. Obsessing on what could have been will not let you move forward.

Additionally, I lean on my husband, Scott. There is no one else who knows me the way he does. He is always supportive, patient, and understanding when it comes to the big decisions, even when it takes me a long time to land on the actual decision I end up making.

What is one life advice you can give to anyone?

Take your shot – whether it works out or not, you will go through life much happier! Do not be scared to take a chance on something that you really want personally or professionally, because the world has a crazy way of leading you down a path that is best for you. I am not a religious person at all, but I do believe everything happens for a reason, the good and the bad.

I look back at my life and think about every single decision I have made, and I wouldn’t change a thing. Some of those decisions may be tough ones to experience. They could make you feel sad, angry, stressed, or disappointed. That’s okay. You get to pick yourself up, move on, and choose what happens next!

I will continue to take risks and challenge myself by answering the tough questions, because I know that in five, ten, and fifteen years when I look back at where I am, I will know that I am exactly where I should be. Don’t give up! Recognize that you may not be in control of all the steps along the way, but that you are in control of the final outcome. Avoid comparing yourself to others, because some people take the elevator and others need to use the stairs.

Please finish this sentence: If you really knew me, you would know that ______. 

I am extremely passionate about anything that I do. I work very hard for everything I have in my life and I do not take the things I care about lightly. I might come off as aggressive, abrasive, or that I lack empathy, but that could not be further from the truth! In fact, I would hope, that the majority of people who know me would say the opposite of that when asked the type of person that I am.

My entire life I have struggled with my words. I tend to have what you may call “word vomit,” and this is something I will always have to work on in my personal and professional life.

The people who really know me and understand me – know that I am coming from a place of deeply caring and that I have a huge heart. 

The people who know me and my story know that I did not get to where I am today by playing it safe, holding back, or most importantly, by not making a ton of mistakes along the way.

To me, life personal or professional is about being authentic and being yourself. It may not be everyone’s way of doing things and it certainly does not appease everyone 100% of the time, BUT if I can go through life knowing that I did what I felt was right – I know I will be living the way I want and not by anyone else’s standards. 

So the people who really know me will read the above and say to themselves “Yup, That’s Jason!”