In a world where the only constant is change, adapting and innovating are not just optional; they're essential. Kathy Zhu's journey exemplifies this ethos.
As a former senior director and associate general counsel at DoorDash and now the co-founder and CEO of Streamline AI, Kathy has navigated the intersection of law and technology with a keen eye for practical solutions.
Before her time at DoorDash, Kathy honed her skills at prestigious firms and companies such as Wilson Sonsini Goodrich & Rosati and Medallia, where she was involved in complex commercial negotiations and legal operations. These roles provided her with a deep understanding of the legal challenges faced by businesses, further informing her vision for Streamline AI.
Kathy's experience at DoorDash, where she played a key role in legal operations, laid a foundation for her entrepreneurial leap into Streamline AI, where she focuses on simplifying and streamlining legal processes, bringing a much-needed perspective to an industry often bogged down by complexity.
In our conversation with Kathy, we delve into the insights and experiences that have shaped her unique approach to law and technology.
Transitioning into an in-house counsel role
Born into a family of scientists, doctors, and engineers, Kathy grew up with a clear expectation: her future was in either medicine or law.
"My dad said, well, you have two options. You can be either a doctor or a lawyer. So, throughout my childhood, I was dead set on becoming a doctor. I wanted to be able to help people.”
However, during her sophomore year in college studying Biology and English, Kathy realized she was destined for a different path – law.
“That was my first pivot. I dropped my Biology degree, finished my English degree, and then went on to law school. When I became a junior associate at a law firm, I was helping businesses go through funding. That’s when I started thinking, ‘This is where all the excitement is.’ Once I was done with a transaction, they took it forward, and all this magic happened. That’s where I wanted to be.”
This realization led Kathy to transition into an in-house legal role.
Building a startup from scratch
After building out DoorDash’s legal function, Kathy pivoted to entrepreneurship. It began with her acute observation of the chaotic nature of legal work and the lack of visibility in managing diverse tasks.
"One challenge was the chaos of managing everything, pouring in from all sides, from Slack, from email, and not having a centralized place to stay on top of it. And then there was just this tremendous lack of visibility. How much work was I completing every quarter? What was happening? Which teams were sending me the most work? And that visibility problem got much worse when I started to manage a team."
Kathy's firsthand experience in this environment laid the foundation for Streamline AI. She designed a system that could bring order and transparency to the legal department.
"I jerry-rigged my own system, first using just generic free tools. That's when I had my aha moment—the solution could only exist if an in-house lawyer designed the system. Because legal is so particular in how we work that unless you walk many miles in our shoes, they're just nuances you don't understand.”
Embracing this challenge, she taught herself to use design tools like Figma and, with the help of UX-specialist friends, crafted the initial blueprint of what would become Streamline AI.
The puzzle's final piece was finding the right co-founder. Kathy recalls how discussions with her friend Julian, a product and engineering expert, revealed a mutual frustration with the existing systems.
"He said to me, ‘Kathy, I am so frustrated with my lawyers. I don't even know what they do all day. They're blocking my launches.’ I got really mad at him and tried to explain how we’re drowning in work. That's really when we realized that there’s a massive visibility problem."
This shared recognition of a widespread issue in legal departments cemented their partnership, setting the stage for the creation of Streamline AI.
Transitioning to CEO of Streamline AI
As Kathy transitioned to the role of CEO at Streamline AI, her extensive experience as a business-minded in-house counsel laid a robust foundation for her new position.
"Working all these years as an in-house lawyer gave me great preparation for it. We've worked with sales, customer success, finance, marketing, and all business teams as in-house counsel. That preparation gives you an advantage, because as CEO of an early stage company, you wear all of those hats. But luckily, you've already walked a little bit of the distance."
This experience is invaluable for a CEO, particularly in a startup environment where one might have to wear multiple hats.
“Cross-functional preparation makes a lot of sense when you’re on a journey towards being a founder. Plus, you probably have good contacts and outside counsel for the incorporation. That's why I'm a firm believer that business-minded lawyers can make fantastic entrepreneurs.”
Kathy's resilience and ability to adapt to new challenges were not just shaped by her professional experiences. Her life journey, which saw her family immigrating from China to Australia, then to England, and finally to the US, played a significant role in developing her grit and adaptability.
“I learned that you need a lot of grit and adaptability if you were moving, say from a 200-person, all girls grammar school in England to a 4000-person public school in Chicago. But the toughest move was way before, when I left China at the age of six and was placed in a language school in Australia. Overnight, I lost my extended family, who I'd seen every single day.”
The struggles of adapting to new cultures and languages from a young age taught her valuable lessons.
"In retrospect, I am incredibly grateful for that initial, very difficult experience, because it's never been as scary since then—whether it was when I was taking on a new role or moving to a new company.”
Applying scuba diving skills to leadership
As a certified rescue scuba diver, Kathy draws parallels between the underwater world and her role as a leader. One of the most crucial lessons Kathy learned from scuba diving is the importance of staying calm under pressure.
She explains how scuba diving teaches you to manage your breath and remain composed, even in life-threatening situations.
"When you're dealing with a life or death situation, you need to be able to handle pressure and stay calm to be able to correctly manage complicated equipment. That’s what scuba training helps you build—incredible mental strength and equanimity. If you think about it in a business context, when something is really stressful, you must be calm. That’s when you’re able to identify the crux of the issue and come up with a solution.”
Kathy also emphasizes the importance of facing fears head-on.
"The enormous benefit of actually facing your fears is that it becomes easier and easier the more you do it. If you run away from your fear, it keeps following you. So, you can't run away from it.”
She draws on her experience in facing her fears during her scuba diving training sessions.
“One of the things the instructor wants you to be able to do is to continue to breathe and change scuba masks with them underwater. The first time that I did that, I was very stressed about it. My heart rate went through the roof and I started breathing and held my breath for a second, which is what you're not supposed to do. And then I had to remind myself to start breathing again. By the second time, it became much easier. All I had to do was focus on my breathing. So, being under pressure teaches you a new way to focus on the essentials and block out other distractions to bring yourself down and remain calm.”
This philosophy is pivotal in her leadership style. Just as overcoming the fear of deep water opens up the magical world of scuba diving, confronting challenges in business can lead to growth and innovation.
Leveraging law experience in product development
Kathy’s transition from a legal expert to the CEO of Streamline AI brought a unique perspective to the product development process. Her background as a lawyer played a pivotal role in understanding and addressing the specific needs of legal teams.
“Lawyers who've used clunky legacy software not designed by lawyers know how that feels. So, at Streamline AI, we leveraged my experience from both doing work on the front lines as well as leading a team and baking that perspective into the product.”
Kathy's partnership with her co-founder, who brought a wealth of experience in product and engineering, was a vital component in Streamline AI’s success. This collaboration allowed for a melding of Kathy's legal insights with technical innovation.
“I'm so lucky to have in my co-founder, Julian, who's had 15 years of experience in both product and engineering. Talking to him and other founders, I've realized that it's very rare for both legal and technical expertise to live inside the same body. They're usually two separate people who actually have some conflict. But we’ve figured out a way to make it work. He never shies away from asking the hard questions, which helps both him and me understand the technical and legal perspectives.”
Listening to customer feedback has been another cornerstone in refining Streamline AI’s offerings. Kathy acknowledges the importance of customer input in shaping the product.
“It's challenging for product designers to see the world through the user's eyes if they've never done work in the user's role before. So they need to conduct user interviews and try to incorporate the feedback.”
Embracing new technology in law
Kathy also addresses the broader challenge of market adoption of new technologies in the legal field. She recommends a conscious approach to adopting technology.
“If legal teams don't figure out technology, they're going to get left behind. Their jobs might get replaced, if not by AI, it'll be by the lawyer who figures out how to use AI.”
Kathy suggests studying Jeffrey Moore's ‘Crossing the Chasm’, which details the tech adoption cycle. This cycle ranges from innovators and early adopters to pragmatists and laggards.
Each group adopts technology at different stages, with varying benefits and risks. Kathy advises legal teams to identify where they fall within this lifecycle.
"Look at that lifecycle and decide what part you want to be part of and understand why. Make sure it's a conscious decision rather than just wanting to ignore it because it's happening regardless."
Kathy points out that resistance to change may not always stem from the legal department itself but could be due to a lack of support from business teams or organizational leadership.
“The mindset that needs to shift isn't just legal; it starts at the very top with the CEO on how to resource legal adequately.”
When it comes to procuring legal tech software, Kathy encourages customers to do their homework.
“If you do your homework as a buyer and do your research, you are a much better buyer. You'll be able to ask the right questions and run a very streamlined and efficient evaluation process.”
By being well-informed, legal teams can navigate through the “noise” in the legal tech market and identify solutions that truly address their specific challenges.
Breaking the mindset of resisting change
Adapting to change is not just beneficial but essential. Kathy, with her extensive experience in both the legal and tech sectors, offers profound advice on how to embrace and direct change rather than resist it.
"Identify what your internal dialogue is telling you so that it's not just an unconscious thing that's happening to you. It's very natural to try to grasp onto what's familiar and safe in the face of uncertainty. That's usually the status quo. But change is already happening. It's much better to be able to direct the flow of change and be the CEO of your own life, rather than having the change forced upon you.”
Kathy’s message is clear: Change is inevitable, and our response to it defines our path. By understanding our internal resistance, acknowledging the ongoing nature of change, and actively directing it, we can transform challenges into opportunities for innovation and growth.
To delve deeper into Kathy’s experiences and glean more wisdom, listen to the full podcast episode of The Abstract here.
