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Advisor | Investor | Former CIO in Services (non-Government), Self-employed
I'll give you a couple examples of standout leadership hires: One was an infrastructure architect hire I made. At the time, there weren't enough infrastructure architects that understood cloud. I improvised by looking for somebody that was a network architect, because when you start to understand the cloud, fundamentally it's leveraging the network. What makes these standout individuals special is they're incredibly adaptable. You may hire them for one role, but throw them at any problem and they just have an incredible talent to adapt, to truly absorb and synthesize what's going on to have an immediate impact. Another standout hire I made began as Chief of Staff. Within a few months, I had switched her into leading infrastructure because the individual who was leading that had decided to retire. She stepped in, helped out, did an incredible job. The common theme here is adaptability.
SVP in Finance (non-banking), 1,001 - 5,000 employees
I learned from lots of failures. Having a standout hire is very hard, it's a numbers game and it’s about probability, like baseball. If you get 30% right you're doing awesome. What I really look for is adaptability but more importantly someone who can compliment you. Not looking for the exact skill sets and expertise that you or the rest of the team have, but that missing component. What is the missing component? Trying to fill that gap with the right kind of diverse view can really help you think differently. We use Personality Poker which puts you in 1 of 4 buckets. You're analytical, you're a creative person, you’re an execution-driven person, or you’re a people-driven person. I’ve found that you need a bit of all of those personalities to really be successful. The person I hired joined us as a head of account management to create that function, and then she went on to be head of customer success, and now she's running core platforms.

The true skill set that differentiated her was her ability to connect with people, whether they’re external or internal customers, which was lacking on the technology team. We were very much I's and O's, ones and zeros, trying to solve technical problems, but we were missing the mark on empathy and emotion. Having that perspective supplemented the team really well and became the X factor that really allowed us to move a lot quicker than we were in the past. The way I've looked at it is really trying to augment and supplement what you're missing, so I try to find as many people as I can that are not like me, that would challenge me, to make sure that we're all thinking through the various compositions.
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Advisor | Investor | Former CIO in Services (non-Government), Self-employed

In the case of my infrastructure architect hire, I interviewed him and instantaneously the gut check told me, hire this guy as fast as you can. I trust my gut instincts, and when I go against my gut instincts I invariably regret doing so. He had instant cred, especially with engineers, and that was key, to know the audience and what they're looking for. He knew how to sniff out bullshit with the engineers, and they actually appreciated somebody that would call them on it, because he had that credibility.

Partner in Software, 1,001 - 5,000 employees

When I think about standout hires, the key thing was that they realized they were joining a team where they were most needed. The people who realize that will probably shine the most because they understand that they're coming in to lead a situation, a team, or build a new operation. I've done a couple of those hires in the past where I said, I need you here. It wasn't really about the job and the compensation, it was that they’d do their best work. And so I kind of had that as a philosophy when I was looking to hire. And there were a couple of examples of that, that I've had over the years where people really shone through.

Partner in Software, 1,001 - 5,000 employees
The standout leadership hires I've seen are the ones who have come in and understood that whether it's politics that are happening in the company or in the executive team, they have to navigate their way through it thoughtfully and be able to actually build consensus. Those standout hires can say, “I'm the new person and I don't have any history or reference here, let me tell you how the world works outside of this little microcosm that you're working in.”

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