Q&A with Bessemer's Jenny Gao

Jenny Gao is an investor with Bessemer Venture Partners, based in New York City. Prior to Bessemer, she worked at State Street and Clear Ballot Group.

What attracted you to venture capital and working with startups?

I’ve always been excited by new technologies, but I think my interest in startups actually came from politics. I grew up in the Obama Era, which meant there was a ton happening not only politically, but also technologically. Facebook, Twitter, Airbnb, Uber… I experienced the rise of all these startups and also saw the default for consumer experiences become instantaneous and easy. Consumers expected digital-first and convenient experiences in all other parts of our lives, yet any interactions with the local or federal government were terrible and cumbersome.

The Obama Administration actually really embraced technology. New tech-focused government agencies such as 18F and the United States Digital Service formed and his political campaign was digitally focused and social media savvy, but the experience was still nowhere close to the ones provided by consumer startups. I was really inspired by his charisma and vision for change, but saw a big gap in how his administration’s ideas were executed ( anyone?). As a result, I became increasingly fascinated with the intersection of politics and technology and wanted to find ways to bridge the gap faster. To me, it became clear that startups could be the catalyst.

So, I decided to work at a gov-tech startup that makes the software and hardware we use for election voting systems. This was the first job where I had an immense amount of responsibility and had to wear many different hats. I really fell in love with the idea of a small team creating something new, valuable, and impactful. But, I became frustrated by the long sales cycles and the glacial pace at which county and state government officials moved. I wanted to see whether other industries would move faster (spoiler alert: they do), so I found myself on a sales & trading team at a large bank. I enjoyed the faster pace and the amount of responsibility I was given, but quickly realized that employees had much less autonomy and very little flexibility.

Venture was something I sort of fell into. I didn’t have a lot of prior exposure, but it seemed like a happy medium to both the startup and the twenty thousand person bank: I have a lot of autonomy to pursue areas I’m interested in, a lot of flexibility around how I want to do my work, and a lot of things to do all the time. Plus, I get paid to do what I love – learning about how new technologies can change the world and meeting interesting people trying to build the future. It’s incredibly rewarding to work alongside founders as they execute on their vision.

What does an average day look like in your role?

I’m sure you’ve heard from everyone that no day is the same. But I roughly divide my time into two areas: exploring new investments and portfolio work. When I’m pursuing new investments, I’m either trying to learn about all of the trends and companies in one specific area (we call it “roadmapping” at Bessemer) or I’m doing diligence around a specific company to better understand whether it’s an interesting investment. We try to be as thesis driven and criteria focused as possible at Bessemer and I think it helps guide our new investment exploration.

Portfolio work, on the other hand, has a very broad scope. Sometimes, I’m just helping the team put out random fires. Other times, I'm helping founders think through key strategies around hiring or funding.

What areas are you focusing on?

I spend a lot of time looking at cloud native and data infrastructure. As software is eating the world (thanks A16Z) and AI is the new electricity (thanks Andrew Ng), I think there is a huge opportunity to find great infrastructure companies that will let us make better software and AI products. As a result, creating chat bots, voice skills, web services, and mobile apps across every industry will get easier and faster.

Bessemer also values the idea of a “generalist athlete” so I also spend a portion of my time on very specific areas split across consumer and enterprise SaaS.

How hands on are you with portfolio companies?

Building a relationship with a founder requires trust, particularly when you’re not a partner, and that trust starts with being someone they can rely on for both small and big issues. I try to be the first point of contact for smaller issues, since I know the higher level strategic questions will definitely have the partner’s attention. But, I also think it’s important to provide feedback on the larger questions as well since different perspectives are always valuable.

How is the overall culture at Bessemer?

At the end of the day, the investing processes are largely the same across firms, but the culture is special and different because of the people. We try hard to be intellectually honest while not taking ourselves too seriously – there’s an undeniable amount of luck and good timing that comes with being successful in venture and we acknowledge that we don’t always get it right (check out our Anti-Portfolio).

And lastly, I also continue to be grateful with how generous everyone is with their time. I know we all have a million things on our to do lists and even more emails to respond to in our inbox, but I am surprised time and time again with how willing partners and more senior professionals are to answer my questions. I think there are very few venture firms like Bessemer that so strongly support hiring from within and providing apprenticeship mentoring to talented, but young junior professionals. And that makes it a pretty special place.

What challenges have you faced in venture?

I’m a woman with a small frame and a young face, so I have to work extra hard to establish myself in any space. In first meetings, I will get asked my age or how long I’ve been at the firm with a line of questioning that makes it clear I am expected to explain my presence in the room. I appreciate that any founder will press a VC on their fit as an investor in her or his company, but it’s undeniable that the assumptions of experience, qualification, and belonging given to me are very different than the ones afforded to my other colleagues.

What advice do you have for young women who want to enter VC – whether on the investing, operations, or platform side?

I help with recruiting at our firm and can’t tell you the number of times I’ve received inbound resumes from men. Studies show that men will apply to positions when they’re something like 50% qualified while women wait until they hit more than 80% of the qualifications. So step one is to be alright with reaching out or applying even if you don’t think you’re qualified.There are very few set rules in VC, so step two is to not be afraid of going outside of the ‘standard' process. Connect with a senior level partner. Send over your resume unsolicited with an investment thesis you’ve developed and some relevant companies. Show them what your analysis would be if you were part of the team. Creative hustle is a big part of succeeding in venture, so don’t be afraid to be proactive.

And finally, meet as many people as possible throughout the process. Unlike large companies where you may have no control over who your colleagues are, venture firms are generally small enough where you know exactly who you’ll be working with. Vet your future colleagues. Make sure you like and respect them. After all, you’ll be spending most of your waking hours with them!