How poker and Kobe shaped a Silicon Valley leader

A 2020 survey by Ernst & Young noted that “94% of C-suite women have played sports.” This revealing statistic applies to Webflow CEO Linda Tong even though, by her own admission, she was “a perpetual winner of the ‘most improved’ award” on the high school sports field. A family-nurtured passion for hometown Chicago sports (Bulls and Bears) underscored her career path to becoming VP of Product & Innovation at the NFL, where, as she outlines below, she parlayed similarities between sports and business into her guiding philosophy of leadership and teamwork. 

Tong’s other roles have included General Manager at AppDynamics and Product Marketing Manager at Google, where she helped launch Google Chrome and Android. In 2022, she was appointed to the board of directors at Prezi. Here, she tells Big Think why Kobe Bryant’s intensity continues to drive her, what she considers Bill Belichick’s most important leadership quality, and why dominance in poker can help illuminate a plan for business success.

Big Think: You posted on X that you “watch *a lot* of sports” — when did you first get hooked into sports?

Tong: My journey into the world of sports began when I was growing up and was largely influenced by my brother, who was my idol. I wanted to be just like him, so naturally, his interests became my own. It started with watching football and basketball with him, and from there, it became my own passion. Living in Chicago up until 1998, I had the privilege of witnessing the Bulls at their peak, which cemented my lifelong allegiance to the team. Naturally, this made me a Bears fan, too. These extraordinary moments, when teams come together to create lasting legacies, are some of the most fascinating examples to me of humans pushing the bounds of greatness in an effort to achieve something bigger.

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Big Think: Having worked at the NFL, do you think the arenas of sports and business are comparable?

Tong: I see a lot of similarities between sports and business, a major piece being the importance of teamwork and bringing large groups of people together to accomplish something bigger than any one individual can. Whether competing in a sports league or creating a company, this mentality is important. Building relationships, establishing trust and empathy, aligning on a clear goal, working together to accomplish that goal, winning and failing together, and persevering through challenges is a big part of building world-class teams.

Big Think: Are there any lessons in leadership you have drawn from elite coaches?

Tong: Bill Belichick is known for his communication style, specifically regarding the importance of preparedness, which comes with clear, constant communication. He once said: “Things happen so quickly. We don’t have time for one person to tell everybody what to do. Everybody needs to know what to do in those situations.” To me, that means starting with good communication at a leadership level. It’s about ensuring everyone is aligned and understands where we’re going as a team. It allows you to move fast, TOGETHER. 

In large organizations like Webflow, communicating effectively empowers teammates to drive the business forward, knowing what parts they play and what is expected of them. Things are always moving and changing, so ensuring continuous, clear, and direct communication leaves little room for interpretation and strengthens the teams’ ability to adjust course and iterate as needed.

Big Think: How have you translated the learnings of sports coaching to the realities of team-building during your career?

Tong: To me, great coaches are great leaders. For leaders, it’s important to understand every person on the team plays a critical role. So, it’s imperative to strategically build the team and get the right people into the correct positions based on the team’s needs. For the team, success hinges on mutual trust and consistent support. It’s about recognizing that success and failure are not individualized, but rather, the team succeeds and fails as one. When building a great company, we need to collaborate to accomplish our goals. Understanding the role we each play, and supporting each other for the team’s greater good, is what unlocks that success.

Big Think: Has observing the stamina and dedication of elite athletes inspired you on a personal level?

Tong: When I see elite athletes, I see resilience. They put in continuous effort, practicing tirelessly, pushing their limits, resting and recovering, only to start again. Despite facing frequent setbacks, they keep going, and it is this perseverance that distinguishes them from their competition. For me, I see the ebbs and flows of my career as my training. The many setbacks I’ve faced have given me resilience; with each challenge, that resilience only grows. I’ve noticed it in how I now move through challenging situations faster. These experiences have provided me with valuable perspective, and the lessons I’ve learned have made me more agile and well-rounded as a leader.

Big Think: Are there any athletes in particular whose example has influenced your own work-life?

Tong: I resonate with athletes known for their work ethic. Personally, I have never been the smartest or most physical member of a team. In fact, I often found myself as one of the weaker players on my sports teams growing up — a perpetual winner of the “most improved” award. So for me, I naturally gravitate to people and athletes who have built their reputations on how hard they work. The late Kobe Bryant’s “mamba mentality” is something I try to channel in everything I do. I love that he saw every minute as an opportunity to better his craft, to put in the sweat equity to be better than his competition, and to make himself the best there ever was. While he had natural talents, his greatness came from his hard work. For me, that means putting in the extra hours, having intense focus, always trying to raise the bar for myself, and showing leadership through my dedication.

Big Think: Should leadership be a collaborative journey or are you more inclined towards the singular approach of “founder mode”?

Tong: Personally, I have trouble with the recent hype around “founder mode” and the alternative “manager mode.” In my opinion, the characteristics of successful leadership are exhibited across many great founders and non-founder scaled operators. Whether you’re Satya Nadella or Steve Jobs, I don’t think the distinction of their capabilities comes down to whether or not they are in founder mode.

To me, the best leaders are great because they’re driven predominantly by a passion for the mission and the customers they serve. They can channel that passion to inspire the organization towards a common mission — and if they can inspire their team, they can unlock their full potential. This fosters team collaboration and is something required for impact at scale.

Big Think: You have said that you “love the idea of democratizing technology” — what are some of ways Webflow is accomplishing this, in the era of GenAI?

Tong: Webflow’s mission is to bring development superpowers to everyone — and we’ve done an incredible job so far, helping millions of people build, manage, and optimize powerful websites. AI is the newest way to harness these powers. AI has the potential to accelerate the creative process, transforming initial ideas from a blank canvas to fully realized concepts, allowing visual developers to focus on creating dynamic website experiences. With our design assistant, we’re already witnessing AI automate simple design tasks like style application and content ideation, and we believe the potential is limitless. We envision AI as your companion along every step of the website lifecycle journey, not as a one-off tool. I’m genuinely excited about AI’s potential to democratize how more people can build for the web.

Big Think: You love playing poker — how has the game shaped your approach to leadership?

Tong: Poker has had a meaningful impact on my leadership approach because, like leadership, poker requires a balance of strategy, adaptability, calculated risk-taking, and luck. In poker, your success depends on making rapid decisions based on the hand you’re dealt, understanding your position relative to others, and regularly assessing the moves of your competitors — all while analyzing incomplete information. These same principles apply to leadership. 

Every day as a leader, I need to make decisions with the available information, which requires both balancing intuition and incorporating the data I have, as well as acting decisively. This also incorporates understanding “the table” — whether that’s the team dynamics, the competition, the stakeholder landscape, and more — these all are critical parts of that calculation. 

Lastly, poker reinforces the importance of making strategic bets. The best players in the game aren’t focused solely on survival — they come to win, and it takes big, bold moves to get to the final table. As a leader, I look to foster a culture of big bets and drive the team toward a winning mindset.