Life-Changing Advice from a Silicon Valley Legend

Karen White knows her way around enterprise software. She was previously the President and COO of Addepar, CEO at Syncplicity and was a senior leader at SolarWinds and Oracle, among other legendary companies. She’s one of the most pedigreed startup advisers and investors in Silicon Valley, but her path didn’t start at Stanford — and includes a fortuitous seating arrangement on a cross-country flight.

She stopped by Progressly last week for lunch and shared her insight into making good choices, taking the right risks, and how we can all learn from the best advice she ever got.

Q: You’ve done so much over the course of your career. What opportunities were the most meaningful?

A: The role I’m most grateful for is the first one I got in the technology sector. I grew up in Washington, D.C. and emancipated myself at 14 years old. I didn’t go to college, but someone took a chance and gave me a job as an early computer operator on Capitol Hill. That’s where I fell in love with tech.

I was in the right time at the right place. By the time I left Capitol Hill, there were some 300 offices with computers, I was known as a “computer person” and was still a teenager. I got to be there for the start of a huge industry shift.

Q: How did you come to be a Senior Vice President for Oracle?

A: I sat next to Larry Ellison on a plane when I was CEO at Egis. We had a big debate on technology during the flight, and after we landed he had his assistant track me down. He tried to convince me to come work for him. I said no for a long time, but finally relented because he was taking Oracle in a new direction that sounded really exciting to me. The first team I worked with there ended up being pioneers in streaming video delivery to homes. It was the first time multimedia streaming was cost-effective and scalable.

It was an amazing group of people — Benioff, Lane, Ellison and so many more all working together. On the flip side, I faced a lot of challenges personally and professionally. I was the first and only woman reporting to Larry other than his assistants, and I had just moved my 5-year-old daughter across the country. I worked hard to establish my credibility and keep all the balls in the air.

At Oracle, I learned the value of partnering closely with the technologists. I said, “I’ll teach you how to run a business if you teach me the backend architecture and tech.” Those were some of my most valuable relationships, even as I transitioned into running business development and marketing for the company.

Q: When have you seen teams struggle the most?

A: There are so many great ideas. Turning a great idea into a great product, then into a great company, is really hard. Getting really good at execution is key. Teams often have a lot of trouble moving from having a minimum viable product in a specific market to true product-market fit. Getting there requires you to determine what you offer that no one else does — and that someone, a whole market, will care about. It’s easy to focus only on the feedback you’re getting from early customers, and that’s important. But it’s important to talk to non-customers in your market and try to deeply understand what the problem you’re solving or opportunity you’re creating for them is. Customers are really good at articulating their challenges and opportunities but not always at prescribing the best technology and product solutions to meet those.

At one of my companies, we once built an ill-advised Salesforce integration because customers told us they wanted it. The project ended up wasting time and resources. Had we talked to companies we aspired to work with instead of just those within our early customer base, we could have had more inputs and better prioritization. On the other hand, at the same company, our customers and prospects hadn’t all fully embraced the cloud or mobile yet fully in their enterprises, and weren’t pushing us in that direction. Yet we forged ahead aggressively there, and those turned out to be great decisions and investments. Our customers loved the products that resulted and the company took off. And then, of course, when you do hit product-market fit things go a lot faster — and you need to be ready to scale.

Q: What’s your advice for building strong a team culture?

A: First, set up a clear vision of where you are headed and why you are headed there, so people know what matters, can understand how what they do fits into the bigger picture and make good decisions that are aligned with what you’re trying to accomplish as a team. Everyone is responsible for locking arms, and walking the talk of the company’s culture. And holding one another accountable for that.

Founders sometimes think the key to establishing a culture of innovation is having really creative, brilliant individual contributors who do whatever they want, and can be reluctant to put any guardrails around that. But it’s important to enable people to present their innovative ideas and encourage them to line up around your vision, strategy and some time and resource constraints that all companies face. Adaptability is so important, but it doesn’t mean you get to do whatever you want every morning.

Agree on what data you care about as inputs to your important decisions, and make sure your team is honest in your win/loss analyses, what’s working and what isn’t. This will make decision-making so much clearer than relying only on someone’s gut. And always invest in architecture early. Technical debt is inevitable, but it’s also demotivating and a time sink, and you lose people if you incur too much of it.

Finally, remember that passionate people can get emotional, so you have to ground that passion in maturity and respect. Encourage each team member to hold themselves accountable to the people next to them for doing their part. It’s so vital for people to be transparent in their disagreements and have the hard discussions. I’ve been at companies where we tease that meetings become contact sports (in a good way). But, we don’t make it personal, we get to a better decision, and we go have a beer afterwards.

Q: What’s the best advice you’ve ever received?

A: When I kept turning down the job at Oracle, a mentor of mine said, “You know, you’ve done a great job assessing the risks of going to Oracle. But you’ve done a really bad job of assessing the risks of staying in the seat you’re in.” This advice changed the trajectory of my entire career.

Not only did I ultimately decide to take the job, I also started using this logic to approach decisions I had to make with vastly incomplete information. If you assess the risk of making a change against the risk of not making a change, either way you’ll ultimately focus on risk mitigation on either side of the equation. And I think you become more open to making changes, being innovative and adaptable, even when you’re getting out of your comfort zone. Your decisions will be stronger as a result.

We can’t thank Karen enough for spending her lunch hour with us. To learn more about Progressly and see how our team has been influenced by her ideas, check out our jobs page.