Karen Roter Davis is Managing Partner at Entrada Ventures, an early-stage venture capital fund, where she invests in B2B software and deep tech companies, partnering with founders and executive teams to build successful businesses. Karen has a long history of executive leadership at Alphabet and oversaw internal operations for Google’s groundbreaking 2004 IPO.

Most recently, Karen served as Director of Early Stage Projects at X, The Moonshot Factory (formerly Google X), where she managed and advised deep tech portfolios. She also scaled innovative, early-stage businesses such as Google Transit (now in 18,000+ cities in 64 countries across 6 continents) and AdSense, which she helped grow from near-inception to several hundred million dollars in run-rate (now a multi-billion dollar business). Other leadership positions include General Manager of Strategy and Business Operations at Urban Engines (acquired by Google in 2016) and Managing Director of Venture Capital and Corporate & Business Development at GE Digital.

Karen has held multiple board advisory engagements, partnering with leadership teams on critical technology investment decisions, M&A, and go-to-market product and partnership strategies. She currently serves as a Board Director of Shift4 Payments (NYSE: FOUR) and 360Learning, is a former Board Director at Innovyze (acquired by Autodesk), and is a member of the Lawrence Livermore National Laboratory’s Carbon Initiative Impact Committee. She is certified in Cybersecurity Oversight by Carnegie Mellon’s Software Engineering Institute and the National Association of Corporate Directors.

Below, read Karen’s tips for executives undertaking a career transition, why women are more likely to have to prove themselves, and how Web3 is reshaping the future of the internet.

Tell us about your new role with Entrada Ventures. 

Throughout my career, I have always been obsessed with the possibilities of technology—its fast pace, the opportunities it yields. How it can impact people’s lives for the better. I had been at X on my second tour of Google—I was learning a ton, working with brilliant people. But I was caught again by the entrepreneurial bug. Entrada has a long history of investing, but this itself was an opportunity to join a new fund. We have a terrific foundation and a lot of room to grow. I have known the partners for a very long time (one of the partners and I go back to business school). I knew we would work well together.

What kinds of companies will Entrada invest in?

We look at deep tech and B2B software. This work is now building on the investment and entrepreneurial work that I’ve done in the past at Google and throughout various startups. For example, there are so many interesting opportunities around next-generation computing, whether it’s AI or quantum computing, or even new algorithms that can be applied across different domains. As we look for sustainable solutions to current problems, new materials, and manufacturing approaches are all coming to the forefront.

What are some takeaways you learned going through your recent career transition? 

What became clear to me as I was having conversations with prospective employers is that titles are important to the extent that they reflect a relationship. Titles are an indicator of the relationship I want to have with a company, the value I want to deliver—they are more than just a title, it’s an indicator of a relationship. Thinking that way about titles, while I was having conversations about various opportunities, pressure tested that perspective. I was able to quickly gauge how companies may view me, but also reflect on how I wanted to be viewed and valued.

Women especially need to consider titles. Too often they are told to prove their value, and the title will follow. If you look at statistics, women are much more likely to have to prove themselves; men are much more likely to be given a chance on an opportunity, even if they have similar experience. So in the current market, titles can make all the difference. The right title can propel them forward in the overall arc of their long-term careers.

How has your interest in public policy shaped your perspective on the tech industry?

Historically, the tech industry has shied from businesses that are regulated. It was “let’s not deal with that until we have to.” But now, technology investing is moving to industries like climate, Web3 infrastructure, and so on. These are all areas that are bumping right up against regulation from the get-go. Regardless of the regulatory environment, it’s always important to understand your place as a business in the overall ecosystem and understand the role that government can play, including government subsidies and grants. People need to realize it’s an ecosystem. There’s a role for public-private partnership, a role for government purchasing, what your role in the ecosystem means for regulation, and how that all might affect your go-to-market.

Web3 is all anyone is talking about. What do Athena members need to know? 

With any new technology, you need to think about how it’s going to impact your business. Many Athena members will be at the forefront of adoption, but it may be too early for others and their businesses in terms of what it’s going to mean—its impact. Think about AI and how many businesses are still catching up there. Many businesses are still catching up with cloud adoption.

When you look at Web3 specifically, it’s built on blockchain. It’s the basis of Web3 and it’s been around a relatively long time. Now, you’re starting to see different applications, particularly on the consumer side. It’s like when people built websites—everything suddenly became dot com. Web3 is a new way of reaching consumers, a new way of connecting that is supposed to be more transparent and more secure. People are experimenting with a lot of solutions and opportunities right now. We joke that it’s like the gold rush—there were a lot of people who made money, lost money, and then there were those who made money on things like the picks and shovels and jeans.

How do people who are new to Web3 get involved? 

It’s a bit like gambling. Are you prepared to lose? What are you prepared to learn? What is the amount of investment that works for you? The same rules of economics apply to Web3. You need to think about where the money is flowing, what happens to assets, where you can expect depreciation or appreciation, and what is your window of investment.

You sit at the intersection of funding, entrepreneurship, and technology. What are you most excited about? 

I get energized by good people who are solving important problems. I get energized by people who treat their employees and friends well, who have strong relationships. That’s my baseline. I connect with those people who are solving critical problems with their unique insights.

What advice do you have for aspiring board directors?

My board seats to date have come from my operator roles, not my investment roles. Now I’m going to have the opportunity to bring on independent directors at an early stage. My advice is that you’re not looking for a board seat, you’re looking for a board seat that is a good match for you with good people.

It’s like finding any other job. It takes as much time as a job search and as much thought and as much positioning. It takes as much effort and vetting and thoughtfulness.

What’s something about you that most people don’t know? 

Many people don’t know that I’m a singer-songwriter. I’ve been a theater, acapella music singer, songwriter geek from the get-go.

What’s next for you?

At Entrada, we’ve just kicked off our second fund, we’re just starting to invest. I’m so excited to invest in incredible founders and their up-and-coming technologies. I’m also eager to get a more diverse set of limited partners (LPs) and investors into venture, and help women get more involved in fund investing. I’m passionate about thinking of ways to make fund investing less mysterious.

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