Yong Kim of Wonolo: Five Things I Wish Someone Told Me Before I Became A CEO

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What is important about life is not to fear those moments when things do not go the way you want. Instead, use those moments as an opportunity to learn and grow.

As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Yong Kim.

Yong Kim is the CEO and co-founder of Wonolo, is a two-sided job marketplace that serves over 1 million front-line workers, providing them access to flexible and consistent job opportunities across the United States within minutes. Yong’s mission at Wonolo is to make work flexible and fulfilling for everyone. He is a graduate of University of Chicago and Harvard Business School, and is passionate about technology, leadership, entrepreneurship, education, and empowering women/minorities.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I grew up in South Korea and when I was 12 years old, I had the opportunity to spend a month in the U.S. with family friends. Immediately I knew I wanted to live in America — I felt a sense of freedom — the ability to share my thoughts and discuss what is happening in the world. After years of asking my parents, I applied to high school in the U.S. and immigrated alone when I was 15.

It was a difficult adjustment — I didn’t speak English, I didn’t know anyone at the school and I was living alone in a foreign country before the internet was mainstream. But I had an incredible opportunity to learn, and I took advantage of every challenge that came my way.

I went on to continue my education at the University of Chicago, where I studied economics and mathematics, and later got my masters in statistics and my MBA at Harvard. This path led me to a three-year stint in consulting, and a seven-year career in finance, helping with M&A deals, fundraising and helping companies go public. Ultimately, I realized while it was an amazing job, I started questioning what I wanted to do with my life and career.

While soul searching, I got connected to the team at Coca-Cola through their innovation accelerator program. I was responsible for identifying business problems in their frontline operations. I recognized that I had to spend time in the workers’ shoes to uncover the right issues.

Working on the frontlines, it became immediately clear that finding workers was the biggest problem Coca-Cola (and similar large companies) was facing. The staffing firms these companies used had been relying on the same solutions for 50 years, and it was clear those solutions no longer fit the bill.

As I dug into this problem further, it became apparent that there wasn’t a worker shortage — millions of hourly workers were struggling to find extra shifts to stay above the poverty line, but there wasn’t a clear platform or solution to connect these struggling workers, and businesses who needed them. I helped create Wonolo to do just that.

Can you share the most interesting story that happened to you since you began leading your company?

Before the pandemic, one of my favorite things to do at work was to walk around the office and strike up conversations with as many people as possible. I would give them fist-pumps and high-fives. I would ask them what they were working on and what they were excited about. It was a valuable opportunity for me to connect with the team, and get the sense of belonging. I did it almost daily.

When we transitioned into the 100% remote working model, I missed the impromptu opportunity to connect with each team member in person. When I expressed this with the team, some of them decided to create a life-size cardboard cutout from my picture. They named it “FlatYong.” They then shipped it to one of the team members who would take pictures with FlatYong in different locations (like coffee shops, hiking trails, beaches) and share with the company. That team member would then ship it to the next team member and so on.

FlatYong ended up meeting team members from all over the U.S. and Canada! And real Yong was able to live vicariously (and connect virtually with team members) through FlatYong.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When my co-founders and I started out, we worked hard to get our very first prototype, minimum viable product ready to launch. Once it was ready, however, we had no customers to actually try using it.

We quickly realized that one of us had to figure out how to sell our product even though none of us had any sales background or experience. Since I was the “business” person, while my co-founders were more involved in the product, I took the role of being the first salesperson at the company.

I did not know what sales involved. So, I talked to many sales leaders at other companies, read books, and watched videos about how to sell. Even then, I did not have any idea. On top of that, my introverted nature interfered with me feeling comfortable and confident in selling.

One of the very first things I did was to go to a shopping mall. I figured that it had the highest density of stores and shops, which I thought could be our customers, in one location. I, then, spent the entire day going around and knocking on the door of each store and talked to every manager at the shopping mall. Unfortunately, I was so terrible at selling that even after I offered them our product for free, no one would sign up or take it.

Over the next few months, I learned how to sell more effectively (and efficiently) and was able to land our first 50 customers or so until hiring real sales professionals.

Looking back, I am embarrassed about how terrible I was at selling when I was visiting the stores at the mall.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are too many people — my co-founders, AJ and Jeremy, my executive team, my board members, investors and advisors. But one particular person is my wife, Linda.

People often talk about how difficult and lonely the journey of being a CEO is. More often than not, there are no clear right or wrong answers in many decisions that the CEO has to make. Every problem is unique and everyone has different opinions on what the CEO should do. Even after the decision has been made, doubt continues to linger. The CEO is burdened with immense accountability and responsibility. It’s incomprehensible just how impossible the CEO job is. It takes a real toll on the CEO, both physically and mentally.

When I am overwhelmed with the magnitude and volume of challenges I face, it’s difficult to express how I am truly feeling, including my deepest fears and insecurities, to anyone. I cannot express it to the team because the team may get the wrong sense that the company is not stable. I cannot express it to the board because the board may wonder if the CEO is fit to do the job. In those situations, I turn to my wife.

Although she does not have all the business context and background of the challenges I am faced with, she has always shared with me her honest feedback without judgment. She helps me focus on the right things — who I am at the core, what got me here, what matters in life. She makes me feel truly seen and heard. Even when I don’t believe in myself, she has always believed in me. And that alone has helped me get through all the challenging times.

I am truly grateful to her.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

Having a diverse executive team (and the board) should be a given in 2022, but for those who are still unconvinced, there are a variety of reasons why it’s advantageous from an organizational perspective. When we’re thinking about diversity, we should of course be thinking about race, but we should also be thinking about gender, background, age, experience, education, neurodiversity and so many more attributes that can create a team of truly diverse leaders.

Diverse executive teams produce a wide range of opinions, which helps prevent groupthink and ultimately leads to more creativity in the company as a whole. If your entire executive team thinks the same way, or comes from the same background, there will likely become a point where out-of-the-box thinking is stunted and organizations hit a creative standstill.

From an employee perspective, having a diverse executive team can help build a more diverse company and create a better chance that employees feel a sense of belonging and value within the organization. When your employees see someone who is from a similar background as a leader in the company it can help inspire them that they could get there in their own career, and that there is someone on their side, which can be critical to keeping top talent and showing opportunities for growth.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

There are countless steps needed to create an inclusive, representative, and equitable society.

Of these steps, one of the most important steps is to eliminate bias in the organization and provide opportunities to those from different backgrounds.

When we were searching for a leader to grow our sales organization, the team had a predetermined view about what kind of sales leader they wanted. We interviewed numerous candidates that fit into our own bias. However, we always found ourselves longing for something more and different.

We ended up bringing on a sales leader who came from a different background than many traditional sales leaders. During the interview process, she impressed the team with her strategic thinking, analytical rigor, growth mindset, and deep empathy. She has been one of the most successful and important leaders at the company, helping build and grow the company significantly over the years. She has eventually become the Chief Revenue Officer at the company, and the company would not have been where it is today without her. I am truly thankful for her for taking a chance on the company.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

The most unique job of the CEO is to make decisions that no one else at the company can be responsible for. Not because the CEO is smarter or better than anyone else. But rather, it means that the CEO is willing to accept full accountability for the decisions that ultimately determine the success (or failure) of the company for every single stakeholder, including employees, board of directors, investors, customers, and users. Putting everything on the line is the privilege that every CEO must accept fully.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

Some people believe that CEOs are removed from what’s going on at the front line or on the ground floor — that CEOs don’t know what’s really happening at the company. However, if the CEO is doing a great job, this is actually not true. On the contrary, the CEO may be the first one to observe if something is not right.

The CEO job provides a unique vantage point of seeing the broad picture of how the company is doing, and how each function fits in to create the magic for customers and end-users. The CEO is surrounded by data, information, and opinions from every function. As such, the CEO has to master how to read and prioritize the right data at the right time. CEOs over time develop a sixth sense of identifying when certain things do not seem right.

For example, the CEO may notice that a talented junior member on the team is disengaged by observing from afar even though she/he may not interact with or work directly with the junior member at all. Or, the CEO may assess that the company may face an unforeseen risk based on a set of seemingly innocuous events happening at the company.

What is the most striking difference between your actual job and how you thought the job would be?

The job of a CEO is significantly more difficult than I had thought. At the same time, however, this is the most rewarding and humbling job that has provided me with the most growth opportunities I have ever had. The quote, “with great power comes great responsibility,” resonates with me.

It’s almost akin to being a professional athlete. It’s both mental and physical. You are constantly pushed to the limit, constantly faced with setbacks (and a few wins along the way), and constantly working on areas to improve further. You are competing against the external forces (e.g., your competitors in the market), but mostly, against the noises in your head.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

It’s not that people aren’t cut out to be an executive, but it is an extremely challenging role, regardless of the company or industry. It’s not a role that will appeal to everyone, or that everyone would be good at.

One trait I think is extremely important in being a successful executive is empathy. Leading with empathy is a key to so many aspects of being a great leader — from creating an inclusive, diverse and equal environment to making your employees feel valued and engaged. Decision-making as a leader comes down to a combination of what is best for your company and what is best for your employees. Without empathy, it’s nearly impossible to make decisions that take all parties into account.

One trait I believe a good leader needs to continue developing is adaptability. As we’ve seen particularly over the past two years, the world changes quickly, and businesses need to learn how to adjust along with it. Without an executive’s ability to adapt and grow their mindset, strategy and goals to a new environment, it’s much harder for a business to succeed. One of the best ways to develop adaptability is constantly seeking constructive feedback and listening fully. Arrogance and ego often prevent one’s ability to develop adaptability.

What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

One piece of advice is to prioritize the company culture ahead of everything else including strategy, product, funding, and operations. People often mistake the company culture with doing “fun things” like happy hours, ping pong tables, and free lunches. But the way we define culture at our company is the way we do things, the way things get done. It’s the set of behaviors and values that we expect from everyone at the company when we work together.

Each year, we get together as the entire company, and discuss if we are aligned around the way things get done at the company (we call it the Tao of Wonolo). If there are certain values that no longer resonate with the company, we will revise and modify. The culture is never static. Just like the company is constantly growing, the culture needs to continue evolving. To reflect this, for example, when we recruit and evaluate job candidates, we avoid the word, “culture fit,” and instead, we focus on “culture add.”

How have you used your success to make the world a better place?

My co-founders and I founded Wonolo to help eliminate barriers for people looking to find work — particularly fulfilling work — and connect them with companies in need of workers. Wonolo was built to help support the flexibility of both workers and business needs, and to create a new model of work that brings together people from diverse backgrounds.

By supporting worker flexibility, we’re providing them with the opportunity to have time. Time with their family, time taking care of a child, parent or partner in need, time to go back to school or take skilling courses to further their career. Beyond time, at Wonolo, we’ve committed to paying our workers around the country a local Living Wage to reflect the cost of food, housing, healthcare and more in local economies. We’re also pushing other companies to commit to the living wage, rather than the minimum wage, and allow people to make enough money to pay their bills without worry, and keep from furthering inequities in this country.

Fantastic. Here is the primary question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Don’t take things personally. Being a founder, I used to (and still do at times) take every failure and critique personally. I would feel a tight knot in my belly. I would get mad or sulk. I wish I had learned earlier that this is about building a company together with talented people, not about my personal ego.

2. People are the center of all. When I think about all the business problems I am faced with, the common denominator is the people-related issues. Why is the new product launch getting delayed? It’s not a product issue. It’s often because people from different teams are misaligned and not collaborating well. When you are faced with difficult problems, first examine what kind of people issues there are at the core. If you can get the people-side of the equation right, most of the problems dissipate.

3. Put your own oxygen mask on first. In the past, I always tried to help my team even when I was not in a good place mentally and physically. Over time, I realized that I could not be the very best of myself if I didn’t take care of myself first. In fact, the team wants me to be energized, motivated, and healthy (mentally and physically). I perform so much better in front of the team when I am personally in a great place.

4. Cannot make everyone happy. I am naturally a people pleaser — I want to ensure that everyone around me is content and fulfilled. As a result, one of the things I thought I had to do as a CEO was to keep people happy and drive consensus. However, I realized that my tendency also created a lack of clarity for the team and slowed down the decision making process. It’s not about making a decision that the majority will be happy about. Rather, it’s about clearly communicating to the team why I made the decision, showing them the vision, and aligning them on the roadmap even when some people may still disagree.

5. Have fun along the way. Building a company from the ground up is almost impossible. Odds are against you. Stakes are high and the pressure is constant. As a result, it’s often easy to lose sight of enjoying the journey and the experience. Learning to have fun is a critical part of the founder journey (and longevity).

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Zero percent unemployment rate. If we have a world where everyone can have a fulfilling job with dignity and stability, and no one has to worry about not having a job and a stable source of income, it will be a beautiful world.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“I’m not afraid of storms, for I’m learning how to sail my ship.” — Louisa May Alcott

There are so many things to love about this quote. What it teaches me is that life is full of unexpected events — just constant ups and downs. What is important about life is not to fear those moments when things do not go the way you want. Instead, use those moments as an opportunity to learn and grow.

Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

MacKenzie Scott. I am inspired by how she is planning to make a significant impact in the world quietly behind the scenes (donating $12B to more than 1,200 nonprofit organizations in 2 years). I would love to learn about her life journey and lessons she learned along the way.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Yong Kim of Wonolo: Five Things I Wish Someone Told Me Before I Became A CEO was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.