To what extent is entrepreneurship an innate quality?
Certainly being optimistic, relentless, agile, passionate about building something great, and cultivating talent are core traits for most (but not all!) entrepreneurs. While much of these are likely mostly innate, experience can certainly shape and develop you in many of these areas.
Do you think that entrepreneurs are naturally good leaders as well?
Not necessarily, as sometimes the determination, force of personality, and conviction an entrepreneur needs to have is hard to scale with bigger teams. Most successful entrepreneurs, however, have a passion for cultivating the right talent around them.
Having worked in senior roles within start-ups and global corporates how do you have to differ your style accordingly?
The things in common are pretty clear – passion for team, desire to do something transformational, organisational savvy, agility, etc. What is perhaps most different in a global corporate is the need for more patience, and the ability to influence in complex organisational structures (as opposed to just doing what you want quickly!).
What is the greatest leadership mistake you have made?
I have a real passion for developing great people, but when I was younger, I sometimes pushed key people’s development too fast, which is not fair to anybody. I also sometimes kept people on the team because of their skill set, despite the fact that they were not good for morale – the morale zombies as I now call them. I’m way faster at moving morale zombies out now.
How does the New York tech ecosystem support entrepreneurship and first time CEOs?
I started Site59 back in 1999 in New York, back when there were few tech start-ups. It’s amazing and impressive to see just how far New York has come – so many of us exist now to support each other, which is a real gift. Plus the city of New York is just much better at providing infrastructure for entrepreneurs.
What attracted you to the role at Gilt?
First of all I am a big Gilt customer. I was also on the Board for three and a half years before I took over as CEO. During that time I got to know the team and the business really well and I wanted to play a bigger role. Quite simply, I’m passionate about the transformation of fashion that Gilt is leading, and even more, working with the team at Gilt is an enormous privilege.
How would you define the culture of the company?
Gilt is an incredibly fast-paced environment that is such a blend of right brain and left brain all day given we marry fashion and tech. We are execution oriented every day – we build a new store each and every day and it has to be exciting and flawless. We are innovators at heart, and we aren’t afraid of risk. We have a really open culture – no one has an office, and we have recently begun doing 360s and sharing them with each other as leaders so we are constantly getting better – and we strive for great collaboration. Plus we love fashion.
How have you tried to influence that culture?
There’s so much that makes Gilt special – my job has been to amplify this and then in addition to make sure we collaborate more seamlessly; that we more formally recognise, develop and differentiate for our best people; that we stay focused and communicate transparently how we are doing really well, especially as we grow; and that we are are clear on not just what someone has to do to be a great leader, but just as much, how we expect them to behave – the values we hold dear.
What are the key attributes you look for in your leadership team?
Innovative thinking in big and small ways, passion for results, being someone people love working for, desire to learn and improve, ability to see the night sky from the other side of the world, wearing a team hat.
What are your continued growth plans for the company?
Given all the changes in the offline retail world, we are even more excited about playing the leadership role in fashion for the young and the affluent around the world. We believe in generating daily excitement, and we believe there is a lot of growth for us in greater share of wallet with our exceptional audience, international growth, being more valuable to our brand partners as they transition to a more digital world, and mobile, where we have a strong position.