As an increasing number of Gen Z are joining the workforce every year — around 17.1 million in 2023 alone — this generation (born between 1996 and 2010) is not only thriving in the workplace, but they’re starting to launch their own companies and step into leadership roles.
We talked to four Gen Z entrepreneurs who are changing workplace culture and dynamics with innovative approaches and philosophies, and they shared their unique experiences as young leaders.
Leading with empathy at a Gen Z brand
Celine Chai
CEO and Co-founder of NinetyEight
Celine Chai was entering her final weeks of college when the pandemic hit in 2020, and
suddenly, she could only watch as her four years of hard work seemed to culminate into nothing.
Her job opportunities, internships, and planned future in advertising were all left up in the air. But then Chai and her fellow students got an email from their professors that changed everything. The subject was, “Starting an Agency.” To Chai and her classmates, one sentence in particular stuck out: “If you can’t find a job, go out and make your own.”
So they took all the skills and knowledge they’d learned from college and got started on their first project—then their first pitch, first logo, first campaign, and before long, Chai and two other co-founders had built their own marketing agency: NinetyEight (named after the year they were all born).
In the few years since, their small team has become an award-winning, future-focused creative agency that specializes in fostering collaborative relationships between Gen Zs and brands, and offers services such as consulting, influencer marketing, branding, and social media.
With a growing network of over 650 diverse Gen Z students, artists, athletes, thought-leaders, and changemakers, they help brands understand the “why” behind Gen Z behaviors.
After all, who better to help you understand Gen Z than Gen Z themselves?
Actions speak louder than words
As the co-founder and CEO of NinetyEight, Chai has a hand in every aspect of the business, from operational and financial matters to serving as an account and project manager, as well as overseeing strategy research and influencer marketing.
While much has changed since she fell into the role at just 21 years old, one of her core leadership philosophies has stayed the same—open communication.
“We’re currently only a team of six, and we operate in a non-hierarchical way. It’s very much horizontal management,” Chai says. “We don’t really care if you’re an intern or co-founder. We really want the communication to be two-way equal and just open and truthful.”
She emphasizes the importance of trust—trust in one another’s capabilities and in their ability to perform in a team setting. “It’s very much, you get a task, you figure it out, you work with one another or you work independently.”
The power of understanding
There’s often a misconception that Gen Z can be difficult to work with, but Chai believes that the key to working well with anyone is by leading with empathy.
“If you really take the time to understand everyone's habits and work styles, and really believe that not one size fits all—especially working with this generation and the generation to come—you’ll see a much stronger connection with your mentees and employees,” she says.
The team at NinetyEight thinks of it as caring about the team holistically, not just in terms of their work, but their entire being. “We’ve worked really, really hard to create a strong culture that allows people to have workplace flexibility while still building good rapport with one another,” Chai says.
This can be challenging when you’re a fully-remote team, as NinetyEight is; half the team is based in Asia, and the other half is based in LA—with work days that overlap for only four hours each day. But according to Chai, this setup has actually been beneficial.
“We’re avoiding meeting fatigue or overloading front-facing camera work in one day, and promoting way more productivity because people can actually get their work done in that four hours of independent work time,” she says.
When they do have those connections, every second of that group time counts. “We’re notorious for having fun,” Chai says. “I think we’ve built a culture of silly little birthday videos, theme celebrations, work parties to destress. When you build an environment that's positive, fun, and upbeat, that's motivation in itself — to one: stay at a company, and two: do your best work.”
Explore—and share—your passions
The company culture also prioritizes work-life balance. The NinetyEight team has conducted studies and found the top priorities for Gen Z when looking for a workplace are pay and benefits, followed by workplace flexibility.
“I have my primary degree in dance, and my secondary degree is marketing,” says Chai. “Work-life balance allows me to pursue passion projects. I have the flexibility to teach, or fly to different places and do master classes.”
Within their team, people are passionate about everything from crocheting and golf to video games, and everyone genuinely takes interest in one another's projects and creative explorations. Knowing that you’re not being judged for doing what you love or making money in different ways helps everyone maintain a good work-life balance.
Age is but a number
Being a younger boss doesn’t come without challenges—even though the team is “tiny but mighty,” numbering no more than nine at any point so far in their journey. For Chai, the first hurdle was actually accepting the leadership title.
“For the longest time at NinetyEight, all the three co-founders hated the idea of a C-suite title like CEO, CFO, or CMO,” she says. “But part of realizing that we’re leaders is being unafraid to give yourself a title and own it and know that we've worked hard to serve this title and live it every single day.”
That confidence was hard-won. Their age often meant other people discounted their professional abilities, and didn’t take them seriously. “When we first started, we heard, ‘Oh, they’re just kids. What do they know?’” Chai says.
Ultimately, the team’s young age worked to their advantage. Since NinetyEight offers such niche Gen Z marketing, businesses now come to them specifically to connect to the young generation.
“My expertise is that I am a Gen Z consultant with lived experiences, I have the tools and capabilities and experience in delivering it through marketing campaigns and research,” Chai says.
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Building trust through open and honest communication
Jake Aronskind
CEO and Co-Founder of Pepper
In the summer of 2019, Jake Aronskind and his best friend Matthew Schkolnick had both just graduated college. Aronskind was about to begin his job in New York City at a proprietary trading firm he interned at the summer before. Schkolnick was about to start a Masters of Accounting program with a secure job lined up for January 2020.
Then, around midnight one night they were together in their childhood hangout—a backyard shed—and had a conversation that would change both of their career directions. Schkolnick showed Aronskind a cooking GroupMe he had recently been added to, that had multiple posts per day.
This led to a conversation about how much food and cooking content existed across the Internet: on social media, apps, digital media—any and all platforms. But something was missing: Yes, people used all those platforms for their food and cooking content, but none of it actually enhanced their cooking experience.
Their idea? A social app to share recipes and what you were cooking with people you know, combined with the tools that helped you become a better home cook.
From quarantine cooking to Gordon Ramsay
Unfortunately, it wasn’t the right time. Aronskind was starting his full-time job. Schkolnick was starting a Master’s program. The idea was put on the backburner (pun intended). But when the world changed in 2020, so did their plans.
Aronskind lived at home during lockdown while keeping his full-time job, and like so many people stuck at home, he began cooking for his family—dishes like eggplant parmigiana, fried rice, sourdough bread—and saw many of his friends doing the same.
“I use Strava, a social exercise app, and I loved the idea of sharing what I was cooking in a similar way,” Aronskind says. “It didn’t exist, so we decided to build it.”
He and Schkolnick knew they had to differentiate themselves. Many of their competitors seemed to have tried to tackle the entire food space at once—cooking and restaurants—and failed because there wasn't a specific core initial audience.
Their vision: Pepper, a platform that was approachable for the everyday home cook and offered true utility to them.
“There are two key incentives for users,” Aronskind says. “First, this is an app for food only. And second, we have tools to help you with that. Many apps just solved the first part in curation but didn’t really help to actually support the culinary-focused content.”
They launched, and people—including Gordon Ramsay—took notice. Today, Pepper is a community of 1 million home cooks from all backgrounds and skill sets that have shared and discovered more than 100,000 recipes from around the world.
Users can also create digital social cookbooks, view standardized recipes, and search the community for dishes based on ingredients, dietary restrictions, difficulty, and more.
The ingredients for success
Cooking is one thing, but how do you navigate leadership as a Gen Z co-founder of a growing company? Aronskind emphasizes the importance of full transparency and open communication.
Despite being remote, most of the six team members live in NYC, so they gather for in-person meetings once a week for an hour. The key is ensuring clear lines of communication at all times. They use Slack for daily messaging, but Aronskind says the most important thing is frequent video calls—FaceTime, GoogleMeets, etc.—with the entire team.
“Sometimes it's easy to fall into the trap of only knowing what you have going on,” he says, “but hearing about the successes and struggles of other team members helps to maintain seeing the bigger picture.”
“Building an early-stage startup means a lot of ups and downs, so it’s important to keep your team in the know. If you’re open about how things are going, nobody will feel blindsided by anything,” he says. “It’s also crucial to keep everyone motivated and continuously paint the long-term picture of what you’re building.”
When it comes to getting that work done, Aronskind feels like their generation allows more freedom for employees. “We are a deliverable-based company, not a time-based company,” Aronskind says. “All I care about is delivering a final product. Not how many hours spent, not how many emails sent. If you get your work done, you can do anything you’d like.”
Driving social change as a Gen Z leader
Jenk Oz
Founder and CEO of Thred Media
Jenk Oz is only 18 years old, and he’s already a social entrepreneur, change activist, speaker, and founder and CEO of Thred Media—but he’s actually been at it for over 10 years. At just eight years old, Oz wanted a way to share all the extra-curricular activities he was taking part in every week with his classmates so they could join in on the fun.
After talking it over with his parents, he presented that same idea at his school assembly. What started as a simple email to his classmates about the latest in fun activities, extreme sport, sneakers, gaming, music, and much more, quickly spread across wider communities and schools, shared by both parents and peers.
Soon, he built out the idea of iCoolKid Ltd., launching it in early 2017. It became a one-stop digital publishing, media, and production company that produced original content aimed to motivate Gen Z to pursue their passions at every turn. It also made Oz the UK’s youngest CEO.
From awareness to action
Along the way, young people began reaching out to Oz, sharing their real-life personal situations. At first, he received a couple of messages a week, but over the next two years, it grew to multiple messages a day.
“Each one gave me a better and more realistic understanding of what other Gen Zers were going through from all corners of the planet,” Oz says. “It made me realize that I was naively unaware of the plight of the very Gen Z community I was supposed to be representing.”
“The topics spanned the spectrum of social change issues, things I was so unaware of, having grown up in a safe, clean, and progressive household,” he says. “Whether it was gay teenagers in Russia who were feeling suicidal because they were unable to come out to their parents, young girls using litter from garbage bins as feminine hygiene products, small rural schools trying to eliminate the use of plastic straws in their community, or very young teens digging out trenches near their schools to get clean water.”
After hearing hundreds of heartfelt stories, Oz started to reflect on the purpose of his platform and its long-term goals. He wanted it to have more long-lasting meaning and strive for greater levels of education, ultimately leading to actionable steps and impactful change at scale.
“In 2019, I embarked on a new journey,” Oz says. “First, I renamed iCoolKid to Thred. Second, I refocused the content to be 100% social change; not just part, but the whole thing. Next, I repositioned the demographic, moving from 8- to13-year-olds upward to 16- to 24-year olds. Lastly, I restructured the company to include consulting alongside the publishing vertical.”
In July 2020, he officially launched Thred.com—a whole new website that was 100% social change-focused, and then Thred Media two years later.
Gen Z goes global
Today, Thred Media is a social enterprise that is built on three pillars: publishing, the Thred Media Community, and consulting with brands to better understand Gen Z. Oz says their goal is to be a positive and unifying force that will galvanize social spirit by supporting and integrating globally with the Gen Z movements.
People—and huge companies—soon took notice. Their client briefs have included Coke, Microsoft, Google, Snapchat, Dunkin, Ford, Vodafone, Lego, Ogilvy, Edelman, United Nations, Epic Games, Global Citizen, Enterprise, Universal Music Group, and Talenthouse.
They are Gen Z—from the 14 people in the Thred Media London office to the 20 remote writers stationed globally. The central tenet of the publishing business is the website, which houses daily coverage and analysis on all aspects of positive social change. They have readers in 220+ countries/territories and the content is available in 17 languages.
In addition to the full-time in-house editors and writers, Thred has built out a global ecosystem of 20 young journalists, entrepreneurs, and activists who want to share their journeys in what Oz describes as a “refreshingly authentic and transparent 'on the scene' reporting style.”
The second area of the company’s focus is the Thred Media Community, which has grown into a global roster of like-minded young people who Oz says, “can network together to drive local change, and then share their stories and successes with other communities.”
“The third pillar is the consulting services, where we help companies and brands understand the beliefs, behaviors, and transformational forces motivating Gen Z employees and consumers,” Oz says. “We encourage brands to communicate and execute inward before selling outward—employees are your best organic marketers.”
Seeing a plan for the future
Today, Oz’s employees range in age from 18 to 33, and he's discovered that managing people and their unique characteristics is “the hardest job you’ll ever do.” His secret: To manage people the way they themselves want to be managed.
“By creating a work environment that works for yourself as a Gen Zer, you by default create one that works for other Gen Zers,” he says.
When it comes to Gen Z, here's what he's discovered matters most: flexible work hours and days, especially the ability to accommodate for unpredictable emergencies, more internally run programs for mental health education, and a place to go if they feel they need help. They also want to see more diversity and inclusivity in hiring and training, and technology adopted at a faster rate—-closer to how they adopt and try new technology themselves.
“When it comes to communication, more is better—-short bursts more often versus once a quarter, especially when it comes to performance feedback,” Oz says. “They want higher quality of content being communicated to them—more business chat that includes strategy, product innovation, and a forward look into the company’s plans.”
There's also a desire to be heard, and as a leader, Oz gives his team opportunities to speak up. “They want to feel like their ideas matter and that they could influence corporate programs and be allowed to move about internally with ease,” Oz says.
“Gen Z wants to be able to see a future together,” he adds. “Employees want to understand the long-term vision of the company and where they fit in. I provide support, mentoring, upskilling, and the possibility to move and experience all parts of the company.”
Have a greater purpose
The key takeaway for Oz? A company needs to have and share a meaningful purpose that matches the moral compass and values of its employees.
“Social change becomes part of your operating system,” Oz says. “This means next-gen-led collaborations and partnerships with top local activists, influencers, and enthusiasts, being involved in culturally relevant causes and events, and reacting, getting involved, and taking a stand on a timely basis.”
This purpose is seen in every facet of the company—whether it's their dedication to diversity, equity, and inclusion (DE&I), the commute experiences of their employees, their efforts to minimize waste, or their management of office materials and supplies.
“I do have to work harder because I’m a founder and yes, I have to work harder because I am the youngest person in the company,” Oz says. “I still have such a long way to go, but working with young people every day is rewarding, and a fantastic client meeting where they make you feel valued goes a long way toward making you feel like it’s all worth it.”
Empowering decision-making and growth
Andrew Roth
Founder and CEO at dcdx
When the pandemic hit in March of 2020, Andrew Roth—now founder and CEO at dcdx—felt a fundamental shift in the world as he knew it. For him, at age 21, it also sparked a transformative beginning.
“Summer of 2020 was truly a pivotal cultural moment showcasing the disconnect in culture between organizations and young people, beginning with the response to the pandemic and magnified by the murder of George Floyd and the Black Lives Matter movement,” Roth says. “What became glaringly obvious at that point was not only that disconnect, but the way in which organizations were trying to bridge that gap.”
Roth had studied Human and Organizational Development at Vanderbilt, and says the one thing he learned, and primarily observed, was that the way research was conducted seemed out of touch with how young people like himself communicated and behaved.
“A 60-question survey to rate our professors was pretty much only done through click, click, clicks just to make sure we could get our grades counted,” Roth says. “That made me think, ‘How likely is it that a 16-year-old’s opinion of 60 different questions, requested via email on the computer about a brand, actually reflects the true beliefs, thoughts, and values of that Gen Zer?’”
“So—at a time when opinions and beliefs of young people mattered and were sought after most—and when the methods used to collect them were least trustworthy, came the true purpose and vision for what would become dcdx: to make the future human,” Roth says.
Transparency from the top
Today, dcdx works to truly understand a brand’s audience through their Gen Z approach to research, translating those insights into actionable strategies to attract the young generation.
“Working with leading tech brands like Google and YouTube, iconic restaurant brands like Chipotle and Denny's, impactful nonprofits like WildAid and Vote America, and some of the biggest agencies in the world like WPP and Havas, dcdx helps the world's top companies get to the heart of Gen Z,” Roth says.
“With an innovative research network of over 100,000+ Gen Zers and a proprietary brand analysis tool the GenZ Score®, dcdx uses methods that help reveal the real and raw behaviors of Gen Z, allowing them to understand and build for this generation in new and impactful ways.”
Roth says their first step is simple—start a conversation.
“Connecting with Gen Z always seems like some ambiguously scary task, and it can be,” Roth says. “But Gen Z are people, they are humans, and they’re the humans that shape our present and our future. Approach them, research them, market to them, and sell to them as you would do the same for anyone—by doing it as humans.”
As a young founder and CEO, Roth also adopts a human approach to his leadership style for a team of six full-time employees. He admires leaders who empower others to become leaders themselves—not just followers.
“My leadership philosophy reflects that—how can I create and enable more leaders on our team and through our work? Leaders at dcdx need the context to reach informed decisions, the clarity to understand their impact, and the confidence to make them,” he says.
“Each part of that is critical for building an organization of leaders. It’s my job to find—and develop—the people that are capable of that, and to give them the platform to find and develop that in others.”
Roth also notes that being remote from the start made him really intentional about building a culture that has put their team's communication styles, language, habits, and traditions under a constant magnifying glass.
“Every single thing we do in a remote environment contributes to culture, from the upper and lower casing of our letters, to the way we end a Google Meet, to the punctuation we use at the end of a Slack message,” he says.
Speaking of Slack, that’s what they use for communication—discussing the details of projects, sharing random thoughts on trends, and more in open, full-team Slack channels for each of their different work streams, regardless of who is involved.
They use Notion for all of their work, which is also entirely accessible and public to all members of the team, and they also build and share Notion dashboards with their clients, working alongside them, to ensure they have 24/7 access to the live progress of the work.
“Transparency extends into the business through our weekly company-wide standups to understand the state of the business, and into every element of the business,” Roth says. “These measures, as a sample of many more, are part of the process we take to ensure context is not a privilege, it’s an employee right.”
Leading by example
As a remote team scattered across time zones and continents, the dcdx team has also been intentional about their approach to work-life balance—a choice that Roth emphasizes must be reflected from the top down in the organization.
“I’m a big believer in the power of habit, and in our innate desire to be consistent in our actions. If my work-life balance isn’t there, I will not expect my team to keep their own,” Roth says.
“I am at my best when I have the space to rest my mind, which requires sleep, exercise, and a life outside of work,” he adds. “It’s essential our team has the autonomy to design that balance in the way that best reflects their personal lifestyles.”
Roth explains that they started this company because they saw a world where Gen Z voices weren't being heard.
“That same purpose has gotten us to where we are today—to a place where we have created a living, breathing entity, built by a vision to create the world where we bring Gen Z voices to the table. We’re a generation making strides to make brands purposeful, to create authentic relationships with consumers that add not just product, but true meaning and value to our lives.”
“There’s no more rewarding feeling to me than getting to collaborate alongside some of the most driven, passionate, and wonderful young people, working on some of the most meaningful topics of our time. I absolutely love what I do and who I get to do it with,” he adds.