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Chief Product and Experience Officer, Upwork

Since his first breath, Sam Bright has represented the sum of disparate parts. So the fact that this ambitious, earnest, biracial son of a midwestern American mother and Ghanaian father earned degrees from little‐known Taylor College, one of the oldest evangelical Christian universities in the nation, and Harvard Business School, one of the most brazenly boastful and revered institutions on the planet, should come as no surprise.

Whatever you imagine the distinctions—or discrepancies—to be between his formative influences, this seasoned 38‐year‐old tech executive is a seamless standout product of it all.

An intensely focused high achiever from a young age, Bright was going to follow his parents' footsteps and become a pastor. Second‐guessing that plan late in high school contributed in part to a father‐son rift that changed his life, but he has remained true to his own values and chosen path, while continuing to search his soul at every fork in the road.

His track record so far includes impressive runs at eBay, Merrill Lynch, and Forrester Research, where he was its youngest industry analyst. He has been noted for his steady hand at growing multi‐billion‐dollar P&Ls, executing high volumes of complex domestic and global transactions, and leading large teams through critical inflection points. At Upwork (branded as “the world's largest work marketplace”), he leads an 800‐person global team in product, design, and customer experience. He is also currently intent on mastering a relatively new role, as dad to his very young son.

My dad was from Ghana, my mom was from Indiana; they met at a ministry conference in Miami and raised me as a double‐pastors' kid—an only child—in Peoria, Illinois. When I was three or four, my dad changed our last name from Nutakor to Bright, and I've often wondered how that has changed the course of my life.

He was an only child whose father passed away when he was young, and his mother passed shortly after I was born. He moved from Ghana to London years before he moved to the States, and he did not stay in touch with his family. So my sense of heritage was a little underdeveloped because the one source that could tell me about it had moved away from it, and my name doesn't reflect it. Even today, when I tell people that I'm Ghanaian, there's always a bit of surprise, especially from other folks who are Ghanaian.

Here I am, the son of a first‐generation immigrant in my dad, and my mom, who told me that, at least on one side of her family, she could trace her lineage all the way back to John Paul Jones, the Revolutionary War commander. So I always felt a simultaneous sense of otherness and duality. And being the product of those different worlds, combined, definitely made me more of a lone wolf.

Peoria, where I grew up, is sort of this microcosm of the culture of the country. Caterpillar [the nation's leading manufacturer of construction equipment] was headquartered there while I was growing up. It was also the birthplace of Richard Pryor.

I went to a small parochial school that was very good to me and invested in me in many ways. And yet, there weren't a lot of folks who looked like me in that environment—and not a lot of pastors' kids either, even though it was a parochial school. I have memories of my parents counseling folks, going to hospitals, and visiting members of their congregation to try to look in on their needs, and that imbued a sense of mission in how I see the world.

Duality is an overarching theme threaded throughout my journey. Being the only, the first, and the youngest, and eventually having that marry with achievement and all the expectations, ideas, and agendas associated with it, is something that I have become more reflective on over time, both as a person and a leader.

As a kid, I competed in spelling bees through both the Association of Christian Schools International (ACSI) National Spelling Bee and the Scripps Howard National Spelling Bee, which is the one that's on ESPN. Starting in third grade, I just joined on a lark. The winners got trophies and the losers got cookies. As you got older, the trophies got bigger.

I competed for five years and went to both of those national bees, three years in a row. I was making progress each time (in my third year, I won the [Scripps Howard] city bee, I won the regional, and I went to the nationals) but, as I progressed, I felt that I stood out more, and not always in a positive way.

There weren't that many spellers who were going to the national bee over and over again. There weren't any other spellers who were going to both the ACSI and the Scripps Howard. And Peoria hadn't been represented that frequently in one of these spelling bees, much less both. You layer on the complexity of my ethnicity, of being Black, of being a pastor's kid, and these things compounded and funneled into my definitely feeling different.

We couldn't afford coaches; we just had to do it on our own. I studied all year long for an outcome that took maybe 30 seconds, and it was very solitary. But I got comfortable with competing and I got very comfortable with alone time. I still am.

Both of my parents attended the bees. If I won, there was a moment of celebration; then my dad would always remind me, “Okay, now you need to start studying for next year.” My dad was very much a person who if I brought home a 95, he would ask me where the other five points were. If I brought home a 100, he'd ask, “Was there extra credit?”

I competed in 40 spelling bees, winning 32 of them. The ability to win and to lose—and the difference in how that feels and how you need to show up with graciousness in both of those moments—really stuck with me. I definitely learned that winning is better. But I saw the fragility of it all and just how much luck and fate play into things. You start to [also] recognize that you're always onstage in a way.

It definitely taught me how to cope with pressure. After you've studied the dictionary and spelling lists for five years straight, there's not a lot that fazes you. I used to articulate it as, I've lived a weird life, but it shaped my perspective. And over time, you learn that everybody has lived a weird life.

In a Christian school, there's a lot of emphasis on respecting your father and mother. I did that, and [throughout most of high school], I thought I would become a pastor as well. But, without going into a whole lot of detail, my dad did not treat my mom with the respect that she deserved, and he didn't always treat me with the respect that I probably should have had as well. It was a multifront problem and I had learned how to triage around it, but, at a certain point—I think it was when I turned 16—I realized that I would not be able to continue down this path. So, on February 11, 2002, the day after I turned 18, I moved out.

The family of a friend of mine at school learned what I was going through and opened their home to me. Every year on that anniversary, I call the Wiltons and thank them. What a difference they made in my life.

I didn't realize how poor we were until I moved in with another family. I was used to going to buffets and my dad saying, “Hey, pile up your plate because this is your only meal today.” When I was growing up, it didn't happen often but, as a treat, sometimes I was allowed to get a second bowl of cereal. I remember asking for a second bowl of cereal at the Wiltons', and they looked at me like I was from another planet: their attitude was “have as much cereal as you want.” I didn't even quite know how to process that.

Why does that matter in my journey? It clarified for me that I was on my own. My mom and dad divorced shortly thereafter. The relationships within our family were irretrievably broken. I understood that everything I would ever have or not have would be up to me, and I'd have to go figure out how to make it work. And so that created a hustle and a strength, because there was no safety net.

I see my life in paradoxes in many ways. Where it ties together is that I feel a sense of gratitude and good fortune for amazing folks who saw me and invested in me over the course of my journey. And because of all the different pivot points in my life, I'm acutely aware of how differently things could have turned out. I'm also acutely aware that there are other people in similar situations who, for whatever reason, didn't have those folks who came along and invested in them, and the ultimate question then is, “Well, Sam, what are you going to do about it?” That's what drives me.

I've been very blessed to have folks who've been mentors and who have helped create pathways for me, and I don't really ascribe that to me, I ascribe that to great people who I was fortunate enough to intersect with, who were kind. If certain breaks hadn't gone my way, I wouldn't have even been in a position to go to Taylor [University] or Harvard [Business School]. All these breaks make me feel a sense of responsibility.

I was a deferred admit [to HBS], entering at 23 when most of the folks were entering at 27. In a class of 900, in your first year, you all take the same courses but are divided into 10 sections of 90, and in my section, I ended up being the youngest. I personally didn't observe many Horatio Alger stories in my business school. That was interesting to me.

I remember I was at an investment banking recruiting dinner, sitting with a managing director and a classmate. They started talking about this elite New York City day care that they had gone to or were going to send their kids to, and I felt two simultaneous emotions. One, gratitude as I thought, How the heck am I even here, when during my dad's entire life, he never drew a salary of more than $14,000? I also thought, These day cares probably cost more than my dad ever made.

In parallel, I also felt imposter syndrome. Like, How do I belong here? I already look different. I'm already younger. I'm already from the Midwest. I'm already on my own. I already have these other things that I don't really talk to people about.

I didn't talk about my identity. I talked about being Black, but I didn't talk about all the nuances that were associated with my journey. I was a private person for many reasons, but one of them was that I didn't really like to unpack that.

The truth is, I've felt like an imposter in every role I've ever been in, and it incentivizes me to work harder, but it's given me empathy for other folks who are underrepresented or the only or one of the few, in similar contexts. I learned that between the mix of my private‐person‐otherness‐lone‐wolf‐comfort‐what‐have‐you, I face questions at times, like, What makes you tick? And the ironic thing is that the more that I've been blessed to achieve, it only becomes more othering in some regards.

I applied to Harvard because I realized I knew no one, I had very limited pedigree, and I had no safety net. Even though people were being kind and telling me I had potential, I needed external validation from a brand name.

Then I was deferred: HBS basically told me to get a couple years of work experience. During that time, I had an amazing mentor: Dr. Jennifer Montana, a PhD from Harvard who had her own economic development consulting company. I met her at a business incubator that I was affiliated with in college.

She tells the story that I came up to her and said something like, “I want to go to Harvard, but I don't know how. Teach me.” She spent countless hours reviewing my application, reviewing my résumé, giving me tips and tricks, and eventually co‐signing me and blasting my résumé to 40 of her friends, one of whom was the chief research officer at Forrester [Research]. And that's how I ended up going from a Christian college in Fort Wayne, Indiana, loading all my stuff in a rented van, and driving 13 hours to Cambridge, having not really known what Forrester was until that moment she connected me with them.

While I was at Forrester, HBS connected me with several other African Americans, one of whom was in the school at the time. I remember going to drinks with him and three or four other folks, and having this “aha” moment. Some article had come out about the number of African Americans in corporate America in senior roles, and I remember saying, “If it's not us, who is it going to be? We are the ones who have been privileged enough to be going to this school.”

Basically, I told my friends at the table, “We don't have the option to settle for a white picket fence. We have to swing for the fences and become captains of industry so that we can break down the doors of opportunity for those who haven't had the lucky breaks we have had.”

One of the questions that is always out there is about the level of ambition, and is it relative or is it absolute? From a relative perspective, it can be tempting to have a feeling of having made it when certain trappings of conventionally accepted success have occurred. And yet, I think that those of us who have been in privileged positions have an obligation to find the biggest megaphone that we can to pay that forward. It doesn't mean that you always have that megaphone on. In some cases, you're just building to get a bigger megaphone.

I think it's part of why I've spent most of my career in mission‐oriented companies, whether eBay with its sort of economic empowerment for sellers or Upwork, enabling individuals to build their careers through the platform. What we do in disrupting the old paradigms of how people work, who they know, where they come from, and using a platform to do it, parallels my own journey in some very resonant ways. I hope that the work that we do enables folks to have access to more economic opportunities. And if I'm in a position to enable that, I think that makes the world a fairer, more just, more inclusive place.

Nobody tells you the things that you actually need to know to be successful. You kind of stumble into those over the course of time. And yet, technology has a massive role to play in demystifying that information, creating access, leveling the playing field, and helping to do those things at scale. That's part of what inspires me and how I approach things, especially now that I have a family of my own. I realize there are other ways to serve beyond the pulpit, and that gives you a different sense of purpose, and a different sense of hope.

Over the past 15 years, I've oriented my career from the perspective of, How can I be in the rooms that will help people who look like me progress? How can I make my otherness less of an outlier?

There's a weekly number of hours that I spend just being Black, as an executive. Every time a person of color—especially in a leadership position—is thinking about joining a company that I've worked at, I get a call. Every time someone's thinking about recruiting a person of color that is even several degrees removed from me, I get a call. As I've been in more and more fortunate positions, there are more inbounds for mentoring opportunities, coffee chats, making connections for folks to break into careers or be introduced to sponsors of mine, or get coached on how to interview or even give speeches to people of color in different forums and at different levels of openness and engagement, to share what's the real of what's happening. I've tried to be thoughtful about how I use those moments.

I've learned that, in spite of my discomfort at times, bringing my whole self to a position means that some of those [internal] barriers need to come down. In a prior role, I used to write a weekly Slack post, and one of the hardest posts I ever had to write was in the middle of the George Floyd protests. People [expressed] surprise that I was engaging on such a deeply personal level and sharing what it meant not only for me but the fears I had for my infant son.

Leading up to the pandemic, I had a string of losses and major life events. My mom passed very quickly from cancer in 2016. Then, between May 2019 and January 2020, I got married, my wife moved in, my role expanded at work, I joined the Smithsonian National Postal Advisory board, I bought a house, my role expanded a second time, we moved cities, we found out we were pregnant, and my dad passed away at the end of 2019. We were still estranged.

All those things help you feel a different sense of your own mortality and change your time horizons. Combined with all we went through during COVID, it made me think, every day we're writing a line in our obituary, and we think that we have much longer to write those lines than we might.

In my whole life, as the youngest, I've always been looking forward to the next achievement. I used to tell folks to wait 'til you get to the corner office before you don the dashiki. But you and I have a voice, we have real influence, right now. We have ways that we can help contribute to the tide of justice, today. I can't say that I'm ever going to be fully comfortable, because I can't change the fact I'm a private person in general. And yet I am picking my moments, more and more, to be more vocal, because I don't want to waste the platform that I have, even as I'm seeking to grow it.