A Conversation With Jay Wright
We had a great chat with Jay Wright, dad, entrepreneur, real estate mogul, and expert in talent acquisition. Read on to learn about his amazing story!
Tell us about yourself and how you got to where you are today.
I actually started my recruiting career in college, working in a call center and reaching out to UC Berkeley alumni to donate to the school. It was a tough job because you constantly get rejected, but I figured out a way to get people to talk to me instead of immediately hanging up. My pitch was, “Hey, we’re doing alumni outreach. Do you have a minute to talk to a Cal student about their future?”
I got really good at it — to the point where they asked me to find more people like me to join the call center. They didn’t call it recruiting at the time, but I ended up recruiting students to reach out to alumni for donations. I had an agreement with the school that I would get a bonus for every person I brought on board. I remember I ended up staffing the call center with a lot of student callers.
I graduated college during a recession and no one was hiring. I remember applying for jobs and not getting any call backs. I was trying everything to get noticed by employers. I made one tweak that changed that.
I used to put my full name on my resume (Jermon Wright) and wasn’t getting any traction. I then updated my resume with Jay Wright instead, and applied to the same jobs. I started getting call backs. It made me realize for the first time how much bias there is in the job hunting process.
I ended up taking a job at a healthcare recruiting agency in Sonoma. Living in San Francisco at the time, the hour-long commute one way wasn’t easy and the pay wasn’t ideal, but this was a company that was willing to give me a shot, so I took it. I worked hard and crushed my performance goals, and ended up getting recruited into another staffing agency firm, Randstad, and stayed there for a couple of years rising in the ranks to Assistant Branch Manager, responsible for building a branch focused on office administration placements within the agency. I traveled a lot and did a lot of old school business development like going business door to business door, passing out business cards and dropping off marketing materials and cookies. My branch ended up being ranked in the top five in the U.S. at the time.
How did you transition into working in the technology industry?
I wanted to get into tech because I saw where the wind was blowing as I kept up with the latest news and trends. This was really exciting to me and I ended up going to another agency focused on technology placements for large Fortune 500 technology companies. This really helped me learn the lingo and understand the tech industry.
In 2011, we were getting a lot of calls from startup technology companies, but they weren’t the typical client profile my agency would work on, because they were too small with no brand name recognition. I really thought the company was missing out because there was something special about these startup companies and I wanted to explore that. I trusted my gut and took a recruiting job with a startup.
I remember I was experiencing imposter syndrome when I started working for this startup company. My colleagues were extremely smart engineers and seasoned operations experts that I’d never worked around before. It was a different experience from the environments I’d been in before.
To help me get through the feeling of not being able to keep up, I took engineering classes and read whatever I could get my hands on to try to understand what these engineers were building and how they were building it. Not only did I become more comfortable, it helped me better recruit other engineers to the company.
How did your journey as an entrepreneur begin?
I met another fellow recruiter and we started an embedded recruiting company where we would be an extension of a company’s recruiting team to quickly hire amazing engineering talent. It was a really busy time for us. It was just the two of us, juggling half a dozen clients at a time. I remember having so many office key fobs because we would rotate visiting a client office every day. It was such a rush and a great experience.
We parted ways after a couple of years to pursue other interests though we’re still good friends today. I took all that I made from my recruiting partnership and invested in real estate. I was introduced to real estate from a family friend and at the time, I wanted to build passive income and physically own what I was building. Investments like a 401K aren’t tangible and the stock market fluctuated too much, so I thought real estate is the way to go.
While I was building my real estate portfolio in California’s Central Valley area, I also got back into talent acquisition, contracting to do executive recruiting for one company, and building the talent function for two other startup companies before and throughout the pandemic.
I was recently swept up in the market downturn and layoffs in tech, so I took this time to reflect on my experience, and figure out what I wanted to do next. I asked myself, “What tool would I have loved to have when I ran talent for these organizations?” and now I’m on an entrepreneurial journey building that very tool. I’m still in the build phase and very much in stealth mode.
All I can say is that this entrepreneurial journey is quite a humbling experience.
Thinking about your leadership experience, how did the companies you worked for support you in being a successful, impactful leader?
My first leadership role was when I was an Assistant Branch Manager at Randstad in 2005. I was responsible for managing people and hitting certain revenue goals for the agency. It was my first experience with employee relations and culture building while managing these personalities.
Unfortunately, I didn’t have any support in doing this, but luckily we ended up hiring a Branch Manager that had more experience to help. There wasn’t a mentorship program, training, or direct support from my manager to be a better manager myself.
It’s interesting because that’s often what happens. If you’re good at something, you’ll end up being a manager with more responsibilities but no formal support in how to be successful at it.
The best managers that I’ve seen are usually people that are pulled into it, and not people who are gunning for it. To be a good leader, you have to be incredibly selfless and incredibly generous.
In your experience, what could companies do to support someone on their leadership journey?
“What’s missing is the human element of leadership. ”
It would have been awesome to have someone that has been there and done that to help support those going through it.
A lot of what management is about is about making sure the team is on track and hitting goals, but there’s so much more to what makes a good leader. What’s missing is the human element of leadership. What’s being done to support the team emotionally and mentally?
How did you learn that in your leadership journey?
For me, I think what helped is having conversations, listening to people, and making authentic connections. I genuinely want people to do well, and learning about someone and hearing about their needs and what’s important to them helps me understand who they are as a person and how I, as their manager, can help them succeed.
I’ve seen managers in my career who have a different agenda and often hold people back and suppress their ceiling for fear of being overshadowed by their employees. I knew I didn’t want to be that type of manager.
Basically, by experiencing “bad managers,” I quickly learned what not to do.
How do you define success and what advice would you give to your younger self about achieving success?
Success is a loaded word. What success meant to me a couple of years ago looks so different today.
Very early on, my dad taught me not to judge people on where they are because you don’t know how far they’ve come. So to me, success is different for everyone.
For example, if you’re an immigrant and come to another country to build a life, that’s incredible and way more impressive than a traditional upbringing. There’s such bravery and admiration in that.
I’m a lifelong learner, so the way I define success is the ability to learn something new. Even if I failed at something, I would still think that that’s a success because I tried.
Having a learning mindset is success to me. Also, being a risk taker is success to me. There’s something very vulnerable and exceptional about putting yourself out there, doing something you’ve never tried before, and just going for it.
Perhaps it comes down to answering one question: “Do you love what you’re doing? Are you happy? Are you constantly learning and moving forward?” If yes, that’s success.
We’d like to touch upon your experience with Imposter Syndrome. What advice would you give to your younger self about that?
I wish I knew back then how many people fake it to make it out there. I thought everyone was brilliant and I was the only one left out of the conversation.
What I realize now is that no one knows everything. And that’s OK.
Keep moving forward and get comfortable with being uncomfortable.
Do you have any habits or routines that helped you feel balanced and successful?
I’m a workaholic. My mind never shuts off. And I love it. Truthfully, I’m not a work-life balance kind of person. I’m not the guy that can take three weeks of vacation and not think about work.
And I realized there’s nothing wrong with that.
You have to be who you are and embrace that. And how I define balance is the same as how I think about success. Balance is different for everyone.
I actually don’t feel like I’m off-balance because I love working and I still make time for everything else that’s important to me. I make time and appreciate the little moments of life that give me balance.
Another habit I have is doing a ton of research before I jump into something, and I always visualize the end result and put my vision on paper.
What’s the last book you read?
The last book I read was Outliers: The Story of Success by Malcolm Gladwell. It’s interesting because it talks about how no one is really an outlier. People need to be at the right place at the right time.
Takeaways
Every role presents opportunities to learn, achieve, and network.
If you don’t know, you can still learn. Research the field you want to break into.
Use your past supervisors (good and bad) to decide what kind of leader you want to be.
Lean into the routines and work styles that work for you. Balance looks different for everyone.
Interested in learning more about Jay? Connect with him on LinkedIn.
