Name: Charlie Oppenheimer
Job Title: Chief Executive Officer
Location: San Francisco, CA
What was the most valuable piece of career advice that you received?
During the 80’s and 90’s, back in in the early part of my career, I was working for Apple. My coworkers were all incredibly smart, talented and driven people. It was an interesting period because Steve Jobs was gone for most of that time and the void he left had to be filled by those with the capability and passion to do so. Apple was already a big company at that point and I was regularly interacting with hundreds of people both inside the company and outside. The thing that I learned was that smart people tend to think that everything they know and believe to be obvious is also obvious to everyone else. And that “stating the obvious” is a waste of everyone’s time. Not so. Everyone sees the world through a slightly different lens and receives a different collection of inputs. The lesson here is that leaders are the people who realize this and practice a three part approach to communication - context, objectives and details. Context establishes how the immediate subject fits into the larger mission. Objectives describe where we are trying to get to with the subject. The details are the plan, tactics, etc.
What advice would you give to someone starting their career in the tech industry?
To succeed, you must be willing to accept failure. If you are not experiencing any failures, then you are simply not trying enough or stretching yourself to grow.
By the time you start your career in tech, you’ve no doubt had success in a wide range of academic subjects. Many of the people entering tech are used to routinely earning good grades and avoiding any kind of failure. I have found that is not a good perspective to come into technology with its inherent focus on innovation. In fact, the people who will ultimately grow the fastest are the people who are willing to try and fail. You learn more from failures than you do from success because when you succeed, you often do not know which thing you did made the success and you tend not to examine the potential factors very closely. “Of course I succeeded, I always do”. When you fail (even in small ways), ambitious people will aggressively try to understand what did not work and why.
What tips would you give to someone aiming for a c-level position?
Hire the very best people, give them a clear mission along with the authority and resources to act and then stand back. If you are truly hiring the best people, this approach will work well. Hire someone better than you and you will see them doing things you cannot.
Are you particularly proud of any career advice that you’ve given or the career route/development of anyone you’ve mentored?
I’ve been really fortunate in this regard. People who have worked for me over the years are CEOs, senior executives, investors and the like. I cannot take the credit because they were great in the first place and that is why I hired them.
But if I think of the most gratifying situations, I think there have been two categories. The first is the people who I hired very early in their careers and helped them to achieve their early successes. I often would have explicit conversations with them where I would say that my job is to help them succeed and here are some things to try and think about.
The second category has been more recently when I have had the opportunity to coach CEOs and other senior executives. In those cases, it is extremely gratifying when they let me know I have taught them something they did not know or they found useful.
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