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Q - First of all, can you tell us a little about yourself, your career so far, and what you do now?
A - I began my career in government consulting at Booz Allen Hamilton. After almost four years in D.C., I decided to move to NYC and joined Uber, which at the time, in 2013, was a relatively small startup doing primarily black car services. The major difference between these two was how problems were approached. In consulting, I was paid to think deeply about solutions and present a plan, whereas in a fast-paced startup environment, the focus is on arriving at solutions quickly and perfecting execution through iteration. After almost six years at Uber, where I led expansion of various cities and products, I transitioned to an earlier-stage startup, Dandy, which is where I am now. In the last five years, I’ve had many roles across the company and now run the entire Operations division.
Q - What was your experience like transitioning from Uber to Dandy?
A - I was the first operator hired at Dandy, and for the first year or two I successfully built the foundations of our business at the speed and scale it required. But, at around the two-year mark, I realized that I wasn’t fully equipped to lead the company into its next phase of hypergrowth. While I had excelled at execution, thinking strategically on a multi-year horizon was outside my comfort zone. The company brought in someone to take on that role, and I reported to them for the next three years. During that time, I committed myself to growth. I did this because while I knew I would grow organically, that pace wasn’t fast enough for a rapidly scaling startup. So I started working closely with an executive coach who helped me adopt a growth mindset, learn to “give away my Legos,” and continue proactively focusing on my development. This experience taught me that CXOs aren’t born, you have to work at it, which is why I now continuously focus on up-leveling myself and my team.
Q - Can you share a significant challenge you faced and how you overcame it?
A - Two years ago, I took a calculated risk when my boss asked if I wanted to take over our global design operation. This role required me to build and lead teams across different countries while managing a large hourly workforce and reducing costs by 200%. Though I was unsure of how it would turn out, I chose to prioritize learning over success. And I was right! This experience taught me crucial skills like managing a global team, owning a P&L and streamlining complex workflows. It also reinforced my belief that most challenges, regardless of how daunting, can be broken down and solved with a growth mindset and curiosity.
Q - How has your executive coach influenced your leadership style?
A - A key, game-changing part of my personal growth toolkit has been my executive coach, who initially helped me adopt the mindset needed to become an executive. As I’ve mentioned, much of this focused on growth – learning how to continuously evolve and adapt as I encounter new challenges and navigate different phases in my career. Now, our work focuses on active brainstorming, honing in tactics I’ve learned, and holding me accountable to them. In addition to my exec coach, I’ve learned to leverage my colleagues, lead with curiosity, ask all the questions, and use online research to continuously learn and improve.
Q - What is your approach to building a strong team culture?
A - Transparency and feedback are essential to building a strong team culture. I emphasize to all managers on my team that both are non-negotiable. In my view, being candid and honest is the highest form of respect we can offer those who show up to work with us every day, so getting comfortable with both positive and difficult conversations is critical to showing our teammates we care about their development. In other words, creating a space where feedback flows freely allows for personal and professional growth.
Q - What are you currently focusing on in your role?
A - One of my current focuses is fostering a culture of continuous learning and a growth mindset at scale. So far I’ve created this culture by walking the talk and coaching individuals on my team. I am now looking for ways to scale and streamline the way managers develop the skills they need to reach the next level. I've noticed that as I progress in my own career, I see my team members facing similar challenges that I once encountered. Establishing a structured learning environment will help them navigate these challenges more effectively, rather than leaving them to struggle without the right support in place. I’ve started a leadership development pilot program for a few people on my team that I hope will be the starting point – I will report back!
Q - How do you handle high-pressure environments?
A - This may sound weird, but I actually thrive in high-pressure environments where there are lots of problems to solve. Of course, there are days when everything seems to be going wrong, but when I encounter those days, I remind myself that I’ve been through similar challenges before and I’ve always turned the corner. So, when I’m in the midst of those days, I allow myself the space to step away and recharge, while keeping the perspective that it will get better. And, in hindsight, these challenging moments often become the ones where you learn the most or become pivotal moments in a company’s trajectory.
Q - How has having a growth mindset impacted your career?
A - Having a growth mindset has become core to how I operate. Earlier in my career, I didn’t fully grasp that just because I wasn’t already skilled in something didn’t mean I couldn’t learn it. Now, when Dandy or I come across a new challenge, I immediately go into research mode, recognizing that we’re unlikely to be the first to face it. I leverage my network and online resources to identify successful solutions that others have used and then tailor them to fit my company’s culture, needs, and resources. In the past, I would have thought that solving a problem required prior experience with it, but I’ve since learned that applying problem-solving frameworks, research, and first-principles thinking is often all you need.
Q - What is one of the most impactful lessons you've learned in leadership?
A - One of the most impactful lessons I’ve learned is the importance of "giving away your Legos." As you climb the leadership ladder, you can’t progress by simply perfecting the tasks in front of you, you need to expand your scope and responsibilities. In order to do that, you need to actively identify what you’re spending time on, free yourself from those responsibilities by delegating them to others, and create room to take on more. No one else will make that time for you, so it’s crucial to show that you’re continuously ready for greater challenges by delegating effectively.
Q - How do you view your role as a leader?
A - Additionally, I’ve realized that my primary role as a leader is to be a coach, not a critic. I bring a different level of experience and context than my team members, so if an outcome isn’t what I expected, it’s a sign that I need to step into coaching mode. Most people want to do a good job, but if they aren’t, it’s often because they lack the necessary skills or experience. It’s my responsibility as a leader to provide the resources and support they need to succeed. Shifting from “this isn’t good enough” to “I have work to do in teaching you these skills” has shaped how I approach leadership. Coaching, training, and feedback are ongoing processes, and I’ve come to appreciate the importance of building a scalable coaching system as my team grows.
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