Jesse Kaufman – Founder and CEO of ShippingTree

Being able to sit back and analyze my mistakes is something I’m always working on.

Jesse Kaufman is CEO and founder of ShippingTree, a provider of cloud-based logistics and e-commerce fulfillment services for consumer product companies around the world. With Jesse’s experience establishing scalable customer service techniques, he has continued to drive customer retention and increase conversion rates for retailers. As a result, ShippingTree can improve a brand’s visibility, efficiency, and quality of service while simultaneously reducing operating costs, increasing margins and promoting brand loyalty. By streamlining vital operations of global supply chain service providers and seamlessly integrating with online shopping carts, ShippingTree is a one-stop-shop for e-commerce logistics and fulfillment.

Where did the idea for ShippingTree come from?

While working on a distribution deal with a customer at my previous business, I noticed a void in the market for the type of services we offer. Mainly, I realized that we need a complete suite of logistics-related services designed to simplify the supply chain.

What does your typical day look like, and how do you make it productive?

Routine is key. I start every morning with a cup of coffee or tea, a small fruit plate, SportsCentre, and my emails.

However, in this line of work, keeping a routine throughout the day is nearly impossible as there are so many moving parts and variables to account for. When things start going slightly off the rails, the most important thing anyone can do is stay cool. If you panic, you’re going to lose — it’s that simple.

How do you bring ideas to life?

I always start by mind mapping and putting things down on paper. I just think a little more clearly with a pen in my hand.

It really depends on what the project calls for, but I find that bringing collaborators on at an early stage is key to developing a good product or service offering. Bringing an idea to life walks hand in hand with team building. Getting that perfect mix of people together who all bring something to the table is the hardest part — but if you can accomplish that, you’re on the right path.

What’s one trend that really excites you?


What is one habit of yours that makes you more productive as an entrepreneur?

As an entrepreneur, things come flying at you — fast — from all directions. Staying organized and prioritizing tasks properly is the key to staying on course.

What was the worst job you ever had, and what did you learn from it?

I was a stock boy at a major Canadian retailer when I was 15. I was always kind of small in my teens, so lifting 60-pound boxes of clothes all day was really hard work. I guess I learned to lift with my legs and not my back!

All kidding aside, the job taught me a good work ethic and gave me my first view into how product is received and sorted once it gets to the stores. I draw on this knowledge in some small way almost every day.

If you were to start again, what would you do differently?

Learn to program and code.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

As an entrepreneur, setting realistic short-term goals that align with what your company is trying to accomplish long-term not only helps keep your sights focused, but it will also enable your team to more efficiently tackle those goals.

You always have to keep moving. Staying static will kill you.

What is one strategy that has helped you grow your business?

From the inception of ShippingTree, I’ve tried to align the company with bigger players in the industry. Developing value propositions that enticed these companies to collaborate with us was key to our immense growth this year.

What is one failure you had as an entrepreneur, and how did you overcome it?

My first major hire at ShippingTree was a disaster. I was lucky enough to realize my mistake before it really hurt the company, and I was able to identify what to look for in the next candidate by realizing where the initial hire went wrong.

Being able to sit back and analyze my mistakes is something I’m always working on.

What is the best $100 you recently spent? On what, and why?

I bought a Dyson handheld vacuum cleaner off of Amazon Warehouse Deals. I got a $300 vacuum for around $100 just because the box was damaged!

What software and web services do you use? What do you love about them?

I use a task manager called “Task” and it’s amazing. I just needed something that was simple and intuitive, with no added fluff. The simple name of the app couldn’t be more representative of the functionality it contains.

What is the one book that you recommend our community should read, and why?

I’m a big fan of fiction as I find it’s a great way to disconnect. I recently read “A Brief History of Seven Killings” by Marlon James. There’s a learning curve getting used to reading the phonetic spelling of English spoken with a thick Jamaican accent, but the story is well worth it.

What people have influenced your thinking and might be of interest to others?

Harley Finkelstein and Ronnie Fieg, NIGO, Jeff Bezos


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