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7 Questions on Leadership with Neil Steinhardt

Name: Neil Steinhardt

Title: President

Organisation: ClassWallet

Neil Steinhardt, president and co-founder of ClassWallet, is an experienced and successful technology entrepreneur with more than two decades of experience in the payments and online advertising industries.

Together with Jamie Rosenberg, he co-founded ClassWallet in 2014 to help transform how education dollars are spent and provide accountability and transparency to everyone involved.

Previously, Steinhardt was the CEO of Skrill USA, an e-commerce business that allows payments and money transfers to be made through the Internet. He served as managing director for USA, a leading European payment processor. He was vice president of products and services for Via One Technologies and also served as the vice president of product management at IPP of America, a licensed money transmitter with a primary focus on delivering financial services to the underbanked.

Steinhardt began his career as an advertising creative at Trion Advertising in New York City and was a co-founder of the Pet Channel Network, an early internet start-up.

He earned his bachelor’s degree in English literature from Brandeis University and an MBA in international business and marketing from Baruch College. Steinhardt lives in Parkland, Florida, with his wife and two children.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Neil's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Building and maintaining culture. As a startup, it’s easy to create the culture you want as you are involved in every hiring decision and have a working relationship with all of your employees. As you scale, and you get to 50-100 employees, you start to have employees hired by people you didn’t even recruit. At 300+ and geographically distributed, the challenge is greater still. While we spend a lot of time building an award-winning technology and a high-performing team, keeping people aligned with our values takes up a lot more time than I would have ever imagined.

2. How did you become a leader? Can you please briefly tell the story?

I started my career at an advertising agency in New York City, first as a copywriter, then a producer, and finally as an assistant creative director. Project by project, it was very interesting to build teams in such an ego-driven business to bring a creative vision to light. Not every decision is unanimous and you can’t always even find a consensus. Getting teams to buy into a vision, work with tight budgets and deadlines, and give their maximum effort was a real crash course in leadership. Thrive or die.

3. How do you structure your work days from waking up to going to sleep?

While I tend to go with the flow as a general rule, I am a bit of a creature of habit with my daily structure. I wake up around 6 and check my email and Slack because we have development teams 7 hours ahead of us and I don’t want to be a blocker for them if they have any questions. Then I pursue the headlines in the New York Post and Twitter before getting out of bed to start my day. I wash up, walk my dogs, and make a cup of coffee before heading to the office.

When I get to work, I grab another coffee then I make all the phone calls I don’t want to make and tackle the tasks I’m not looking forward to first thing in the morning so they don’t hang over my head all day. I tend to have a lot of meetings so my days are usually varied but hectic.

I try to leave the office most days by 5:15 so I can go to the gym at 6 pm. I work out 4-5 days a week and it's usually 3-4 days right after work. If I don’t have work to follow up on the ride home I try to call a friend or my family to stay in touch.

Once home, my wife and I usually cook and share dinner.

My evening routine is to walk the dogs, watch a little TV, and catch up on some work.

I read every night before going to sleep. I usually go to bed around 11 pm and read until midnight.

While they say it's healthy to get 7-8 hours of sleep I try to get 5-6 hours of sleep every day.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Not blaming an employee for a mistake. Usually, when something breaks down, you have to look to see why we put someone in a position to fail. Did we have the right policy and procedure in place? Did we follow the policy and procedure? More often than not, the blame usually lies with management. We don’t want people to be afraid to do their jobs so our role is to put them in the position to be successful and create the guard rails to minimize risk.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

Either The Lean Startup by Eric Ries or Crossing the Chasm by Geoffrey Moore. I’ve worked for a bunch of early-stage companies and the lean startup methodology has served me well. We should always be iterating, testing, relying on data, and constantly failing. Even as we grow, I still believe firmly in that methodology although we tend to move a lot more slowly and deliberately as an organization. As the company matures, the concepts addressed in Crossing the Chasm are a great model to challenge a successful team to move beyond the success of early adoption and keep them striving to find broader success. The things that made us successful early on are not necessarily the things we need to do to gain broader market success. It's an interesting challenge for the team to reinvent ourselves even when things seem to be going well.

6. If you could only give one piece of advice to a young leader, what would you say to them?

Be humble. The older I have gotten, the more I’ve seen that there are many paths to success. When you hire talented people you need to give them the resources and space to do what they do well, and even let them make some mistakes so that they can learn and grow in their careers. I’ll help people avoid catastrophic mistakes so the lessons don’t have to be painful. Showing humility contributes greatly to fostering a learning organization where people aren’t afraid to take risks or voice their opinions. I’ve been at it for a long time and I still enjoy learning new things.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

One of my favorite lessons comes from very early in my career. My first job after college was as a ski lift operator in Vermont and my boss was a southern charmer named Matson. Matson was a man’s man and I was a recently graduated English Literature major from a small New England liberal arts college. One of the things I had to do before the first snow was to dig post holes in the granite ground with a pneumatic drill (which was heavy and unwieldy) for the maze at the base of the ski lift. So, Matson and I drive this heavy drill in a pickup to the base of the lift and mark out some spots where we have to drill holes. Having no experience with pneumatic drills, I asked Matson what I needed to know and he looked at me with disgust and said “Yeah, take off your f*cking skirt.” (Admittedly, it was a different era in 1990). While he might have been having a joke at my expense the lesson still rings true today (and doesn’t have to be so overtly sexist.) Sometimes you just have to move forward. I’ve worked in venture-backed startups for most of my career and heard lots of variations of this theme (in a bit more PC fashion). 80% has to be enough, you never have enough data, so trust your intuition. However you want to say it, oftentimes in business, you have to go to know.

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