Bill Hildebolt, CEO and Co-founder, gen.video

A highly engaging leader, Bill credits his early corporate career (Harvard MBA, Morgan Stanley and the Venture Capital world) for the experience and knowledge that facilitated his success as an entrepreneur. Known as humble, smart, determined and passionate about his business, read Bill’s views on the challenges of retaining empathy, community and human connection in a virtualised world.

Bill founded the premier performance-based influencer marketing platform gen.video in 2004. gen.video  provides influencers a place to find brand sponsorships and takes things one step further by helping brands drive additional revenue for content published to YouTube through their unique partnership with Amazon, Target and Walmart.

What are you most proud of professionally?

At some point in my career, I would have said that developing innovative products was my proudest accomplishment as there have been moments where my company has leapt ahead and done things that were truly novel. At this point, though, I have a different view – that the most important, meaningful thing you can do is develop people and give them interesting opportunities and experiences. It takes time to come to that understanding because most employee relationships end in what initially feels like a failure: either the employee decides to pursue something else or the firm decides there’s no longer a fit. But then 3, 5, 7 years later you come back into contact and they say, “my time at the company really transformed me”. Those moments instantly choke me up. It’s a little like being in the movie “It’s a Wonderful Life”.

 Who is the leader who most influenced your early career?

You know, I’m going to cop out of this question and say that the thing that has been most profound in my career is that even though I started in the workforce way back in 1991 most of my managers right up until I became CEO were women. And maybe equally important, the only time my career went sideways was when I had male managers. Not only did those women prepare me for today’s work environment where women make equal workplace contributions (See how I sidestepped whether they are treated equally? Born politician this guy J), they were profoundly good people focused on my success and building me up. So I will give it up for several of them: Joanna Nifong and Dale Johnson at Wachovia and Ruth Porat at Morgan Stanley (now the CFO of Google). I consider myself blessed to have worked with them and think about the lessons they taught me constantly.

 If you could appoint anyone (alive, dead, fictional or real) to join your leadership team who would it be and why?

I’m going to cop out again because I’m a little immune to hero worship and tend to believe success is a mixture of great talent for sure but also being in the right place at the right time with the right resources.

Do I admire leaders like Jeff Bezos and Elon Musk? Absolutely. Would I step aside for them? Yup. Do want them on my management team? No. The person I do want on my leadership team is someone who is completely all-in. Willing to storm any hill, who refuses to fail, who is willing to tell me when I’m wrong and able to understand the constraints that we have without feeling victimized. There was a point where I wondered if such a person even existed and then I found one in Jessica Thorpe, and it has made all the difference. And by the way she is a woman.

In today’s VUCA world, what do you see as the biggest challenge for leaders?

Well, first I think that acronym needs a refresh. The world has become much more complex but volatility and ambiguity are rapidly decreasing to the point where a key challenge for business leaders is actually lack of friction and transparency.

Those sound like good things but it is incredibly hard to run a business where the switching costs between vendors is approaching zero and the ability of clients to dissect your business model is high. Except for network monopolies (which is what the tech giants have become), everyone else struggles with low sustainable margins against the demand to continue innovating to stay relevant.

There are precious few “profit harbors” where you can consistently earn a return on capital even to reinvest in the future. Understanding the macro forces you are subject to and then managing within them is incredibly difficult.

How important is it to be empathetic as a leader?

That’s a great question. I believe empathy is probably the most important attribute in being a successful human, full stop. I don’t care if you can’t add 2 + 2, if you can enter any interaction and quickly form an accurate understanding of what the other person is experiencing and needs, you are not only going to be successful in most things but you are going to have an incredibly rich emotional life. And for all of the good press empathy gets, I think most people still score remarkably poorly.

We’re all so caught up in our own stories that half the time we can’t even answer a straightforward question in an email. But now that we’ve established empathy’s bona fides, I am not sure that over indexing on empathy is correlated with being a more effective leader, at least not unless you also have the ability to filter and manage what you do with that empathy.

Empathy is by definition a 1:1 dynamic whereas leaders not only have to think about the group as a whole but they often need to swim against an empathetic response and take the group to places they don’t want to go or don’t believe they can go. Leading and empathy aren’t mutually incompatible but I do think they are different skills.

How do you continue learning when you’re ‘top of the pile’?

I’ll let you know when I get there. Seriously, this goes back to my first answer. Every time I’ve thought we had come up with some unstoppable innovation or had broken through to permanent financial success some new shiny object has changed the landscape or there’s been some other setback that we’ve had to overcome.

The shark analogy works perfectly in tech. If you aren’t moving forward, you are dying. And if you are just asking how to keep learning when you are the CEO and everyone expects you to have the answers, that’s even easier. I’m the CEO of a digital media company whose success is primarily based on the behaviors of 20 and 30 something women. I’m neither one of those things so all I can do is try to keep learning.

What are the 3 most important things (values or behaviours) you look for when hiring? And why?

In order, I think it is

  • Determination
  • Empathy
  • Self sufficiency

Hopefully not too much of a surprise given the answers above and I’d admit they are all highly correlated. The whys are straightforward: determination means you will deliver results and not just punch the clock. That is the most critical thing and so very rare. Empathy not just for the reasons we discussed but because it will make you more productive. You will resolve issues without escalation.

You will delight clients because you understand what they want. You might even understand the challenges I face in running the company and do your part to support me. And self-sufficiency because we are a small company and so there’s no room for people who collapse into a puddle when the toilet is clogged or a light bulb burns out.

 What is more important – acquiring talent or retaining talent?

An impossibly hard question. As a small company we have never figured out the magic formula for definitively identifying great people in the interview process. It’s even a joke that it’s a positive indicator for your career if I didn’t want to hire you…which is also why I don’t blackball anyone, I know I’m fallible.

Once they are in and we realize they are a rock star in the making, we do try really hard to let them flourish and be recognized. We might even try too hard and end up creating more pressure than they want. So I think I’ve given myself away: I think retaining talent is the key to success.

What advice would you share with your 21 year old self?

You can’t do it all by yourself.

What do you believe will be the biggest disruptor to the world of work in the next 5 years?

Everyone talks about the robots taking all of the jobs but I don’t think that’s a 5 year trend and maybe not even a 10 year trend. My guess is that like every other technical disruption in the past, the robots will just enable us to create new kinds of jobs for humans that we can’t even imagine today.

What I do think the big near-term disrupter will be is the continued trend toward virtualization. We have flex time and work from home policies and I understand the benefits they bring. I also understand that as “the boss” I benefit from 24 hour connectivity. But I also feel there is a loss of office culture, collaboration and inspiration to do great things when we aren’t physically together. We used to bang a gong in the office when we closed a sale. No one is going to bang a gong in their home office when a sale is closed. And not only do we lose that human connectivity when people are dispersed but I think flex time and working from home can lead to feelings of inequity because we perceive the other guy is taking advantage of the policy and I’m the only one working. Other companies claim it can work brilliantly but I find it challenging to manage and so I wonder whether I’m doing it all wrong or are they kidding themselves and this is a bit of a disaster in the making.