Leadership Lessons: Insights From Ship Essential CEO David Sitt

Welcome to Leadership Lessons, where we profile executives from the supply chain industry. In this edition, we're joined by Ship Essential CEO David Sitt who discusses his path to leadership, the challenges of starting a fulfillment company, and the key lessons he has learned along the way

Can you share your background and what led you to the supply chain industry? I grew up in Brooklyn and graduated from NYU in 2015. At NYU, I studied Urban Design & Architecture and Business. I worked in real estate and family office venture investments through undergrad. I graduated from Columbia Business School in 2018 with a focus on Venture Capital, Private Equity, and Business Creation. While in business school I launched a coworking company which is now managed by Industrious.

Is there someone you met early in your career that had a lasting impact on you? My dad is an entrepreneur at heart and has guided me in launching products and operations. He’s been able to guide me through the ups and downs of building Ship Essential from the very beginning.

At 16, I interned at Gilt Groupe through the launch of Gilt City. Through that exposure, I saw the value in creating something from scratch and building a team. To this day, the team and alumni have been mentors to me. They have been extremely helpful in helping guide me in the worlds of launching a business and evaluating growth opportunities.  

What led you to start Ship Essential? In 2019 I saw an opportunity with e-commerce brands in that the existing third-party logistics (3PL) offering was broken. Ask any brand and they would tell you how much they hated their 3PL experience. The lack of transparency and communication was a red flag. Moreover, brands who wanted to feel a connection to their inventory needed to fulfill orders internally to maintain that experience given where most 3PLs are located.

Through my experience in real estate, I also understood that the pricing and value of industrial real estate was rising while urban real estate was on the decline. There was a clear opportunity to bring fulfillment into cities due to the converging prices for industrial real estate.

By merging these two ideas, we built Ship Essential to be an urban fulfillment company where brands could feel a sense of connection and maintain open communication and transparency with the team that is managing such a vital part of their business.

What is the most important lesson you learned during the company's first year? Communication with customers is the most important part of building a business. There is no replacement for good communication with brand partners, especially when things go wrong. The fear of reaching out to let a client know something went wrong is so misguided - we should be afraid of not letting them know quickly enough!

What is your favorite and least favorite part of work? I gain energy from my meetings with others. Whenever I get a chance to speak with a brand founder or operator, I’m able to learn more and get excited about what I’m doing every day.

The worst part of my job is when I need to deliver bad news. Operations itself is riddled with issues and putting out fires is part of the territory. Having to deliver that news is brutal. Then again, the opportunity to fix those issues makes my day.

Did you always know you wanted to be in a leadership position? I always wanted to create something. Rather than focus on leadership, I like to focus on the problem at hand and finding solutions with the team.

Can you discuss a time when your company had to adapt to significant change or disruption? We’re still at an early stage of the company but we’re always ready to adapt. We realized that same-day delivery was difficult for us to manage on our own so we decided to outsource it. Then we grew enough where we were ready to take it in-house which meant acquiring carry to provide brand partners a true customer experience advantage via same-day delivery expertise.

Over the last year, we’ve seen retail and e-commerce change dramatically so we’re always working with our brand partners on new services. Some are diving deeper into retail and wholesale (vs. e-commerce), and some are looking to do more ship-from-store where we pick up the inventory from their retail floor. It’s all about staying adaptable so our brand partners can grow.

Can you share a mistake you made as a leader and what you learned from it? I think one of the hardest things to do as a leader is to let go of projects and hand them off to the team. I need to be better at firing myself from roles that the team can take on. That frees us up as a company to work on more interesting things.

When Sean McMahon and Justin Randolph joined the team a couple of years ago, it was difficult for me to let go of certain operational and account management functions. Luckily we have built a fantastic team who knows when to tell me “Don’t worry, we’ve got it handled.” That helps me step back to focus on my other functions that are needed. 

Can you share the best moment you've had as CEO? Every time we hire someone on the team that helps us grow. Seeing the growth of the team has been tremendous and now growing to over 50 employees, those moments have thankfully been abundant!

What keeps you up at night regarding your job? Everything! I'm always asking myself if I missed something in operations, did we sign the brand, or am I blocking the operations team from doing something?

What's the app or tool you can't live without?  Notion. We use it as an internal knowledge base and collaborative tool. I have a personal Notion Board too - it's my journal and note-taker. I even use it to make sure I’m spending time on the right things in my calendar.

What do you like to do to decompress when you're really stressed out? Tennis is my meditation. I try to play at least twice a week.

What do you read every day? Every day I get a ton of newsletters but here are some:

• News - Morning Brew, Retail Brew, Stratechery
• Industry Focused reading - WWD, Business of Fashion, Who What Wear, Eli's Newsletter, Nik Sharma
• Podcasts and Knowledge Building - Farnam Street, James Clear, Daily Stoic

What’s your favorite TV show? Seinfeld