Chapter 1: Embracing Challenges

Life is filled with unexpected turns, and it's crucial not to shy away from moments that deviate from our plans. Instead, these instances should be viewed as chances for growth and learning.

As part of our series titled 'Five Insights I Wish I'd Known Before Becoming a CEO,' we had the privilege of speaking with Yong Kim. He is the CEO and co-founder of Wonolo, a two-sided job marketplace connecting over one million frontline workers with flexible job opportunities across the United States. His mission is to ensure work remains both flexible and rewarding. A graduate of the University of Chicago and Harvard Business School, Yong is deeply passionate about technology, leadership, entrepreneurship, education, and empowering underrepresented communities.

Before we delve deeper into your experiences, could you share some background about yourself and what led you to this career path?

I was raised in South Korea and first visited the U.S. at the age of 12. During that month-long stay with family friends, I felt an undeniable sense of freedom that I longed for. After years of persuasion, I applied to a high school in the U.S. and immigrated alone at 15.

The transition was challenging—I was not fluent in English, didn’t know anyone, and was adapting to a new environment without the internet. Nevertheless, I embraced every challenge as a learning opportunity.

I pursued my education at the University of Chicago, majoring in economics and mathematics, followed by a master's in statistics and an MBA from Harvard. This journey led me to three years in consulting and seven years in finance, where I worked on mergers and acquisitions, fundraising, and taking companies public. Despite the success in these roles, I began to question my true career aspirations.

During my introspective period, I connected with Coca-Cola through their innovation accelerator program. My role involved identifying operational challenges within their frontline workforce. To truly understand these issues, I realized the importance of seeing things from the workers’ perspective.

It quickly became evident that the biggest challenge for Coca-Cola and similar companies was finding workers. Traditional staffing agencies were relying on outdated methods that no longer met the needs of the workforce.

Upon further exploration, I discovered that the perceived worker shortage was misleading; millions of hourly workers were struggling to find additional shifts to make ends meet. This realization inspired the creation of Wonolo, a platform designed to bridge the gap between these workers and the companies that needed them.

Can you share an interesting anecdote from your journey as a CEO?

Before the pandemic, I loved engaging with my team in person, exchanging high-fives and discussing ongoing projects. This connection fostered a sense of community. When we shifted to a fully remote environment, I missed these spontaneous interactions.

To stay connected, my team created a life-sized cardboard cutout of me, affectionately named "FlatYong." They took it on adventures across various locations, sharing photos with the team. This creative solution allowed me to connect with team members virtually while maintaining a sense of camaraderie.

What was one of the funniest mistakes you made in the early days?

When my co-founders and I launched our first prototype, we faced a major hurdle—finding customers. As the designated "business" person, I took on the role of the first salesperson despite lacking any sales experience.

I thought I could learn from others, so I researched extensively and even visited a mall, thinking I would find potential customers. I knocked on doors, offering our product for free, but was met with rejection. This humbling experience taught me valuable sales lessons, and eventually, I secured our first customers by adapting my approach.

Is there anyone specific you’re particularly thankful for in your journey?

While I owe gratitude to many individuals, my wife, Linda, stands out. She provides invaluable support during the challenging moments of being a CEO. The role often feels isolating, and it's hard to share my fears and insecurities with my team or board.

In those moments, Linda’s empathetic listening and honest feedback have been my anchor. She helps me stay grounded, reminding me of my core values and motivations, which has been crucial during tough times.

Chapter 2: The Importance of Diversity

As the U.S. grapples with issues of race, diversity, and inclusion, it's essential to understand why having a diverse executive team is critical for organizations.

A diverse team fosters a variety of perspectives, preventing groupthink and enhancing creativity. A homogeneous leadership group may stifle innovative thinking and limit problem-solving.

From an employee standpoint, diverse leadership inspires individuals from various backgrounds, helping them feel valued and promoting retention.

What steps can leaders take to foster inclusivity and equity?

Creating an inclusive environment requires actively eliminating bias and offering opportunities to individuals from diverse backgrounds. For instance, when searching for a sales leader, my team initially had a narrow view of the ideal candidate.

Ultimately, we hired someone with a unique background who brought fresh perspectives, significantly contributing to our growth. Her success reinforced the value of diverse leadership.

What unique responsibilities does a CEO hold compared to other leaders?

The CEO's primary responsibility is to make decisions that carry ultimate accountability for the company’s success or failure. This role requires a willingness to embrace risk and accept the consequences of those choices.

What myths about being a CEO would you like to address?

There’s a misconception that CEOs are disconnected from the frontline. In reality, effective CEOs are often the first to recognize underlying issues within the organization. This unique vantage point enables them to prioritize critical data and identify potential risks.

What’s the most significant disparity between your expectations of the role and reality?

The role of a CEO is far more challenging than I anticipated, but it’s also incredibly rewarding. The responsibility is immense, akin to a professional athlete facing constant pressure to perform and improve.

Do you believe everyone is suited for executive roles? What traits contribute to success?

While not everyone is cut out for the executive role, certain traits can enhance the likelihood of success. Empathy is essential for fostering an inclusive environment and making decisions that benefit both the company and its employees.

Adaptability is another critical trait, especially in a rapidly changing world. Leaders must be willing to seek feedback and evolve, as rigidity can hinder growth.

How can leaders cultivate a positive work culture?

Prioritizing company culture is paramount. Culture encompasses the behaviors and values that dictate how work gets done. Each year, our team evaluates whether we are aligned with our core values, adjusting as necessary to reflect our growth.

How has your success contributed to making the world a better place?

At Wonolo, we aim to eliminate barriers that hinder individuals from finding meaningful work. Our commitment to paying a living wage and advocating for worker flexibility supports employees in achieving a better quality of life.

What are the "Five Insights I Wish Someone Told Me Before I Started"?

1. Don't take things personally: Building a company is a collaborative effort, not a reflection of personal ego.
2. People are central: Most business challenges stem from people-related issues; addressing these can lead to resolution.
3. Prioritize self-care: Taking care of oneself is vital for effective leadership.
4. You can't please everyone: Focus on clear communication and vision rather than seeking universal approval.
5. Enjoy the journey: Remember to have fun amidst the challenges of building a company.

If you could inspire a movement, what would it be?

I envision a world with zero unemployment, where every individual can find fulfilling work and live with dignity.

What life lesson quote resonates with you?

"I'm not afraid of storms, for I'm learning how to sail my ship." — Louisa May Alcott. This quote reminds me that life’s unpredictability offers opportunities for growth.

Is there someone you would like to have a conversation with?

I would love to meet MacKenzie Scott to learn about her impactful philanthropic journey and insights.

Thank you for sharing your experiences and insights with us!

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