Meet Jeff Alpert

Introduction

As President of Milestone Trailer Leasing, Jeff Alpert oversees the company’s highway trailer division which consists of 25+ locations across the US and 57,000+ units. The company veteran (he joined Milestone in 2000) recently shared what accomplishments he is most proud of and the biggest challenges facing the transportation industry.

Everyday Operations

Tell us about your role as President of Milestone Trailer Leasing. What are your day-to-day responsibilities?

I’m responsible for the oversight of Milestone’s highway trailer division which consists of 25+ locations and 57,000 units. My role is to help make everyone around me successful and get obstacles out of their way.

What accomplishments are you most proud of?

I’m proud of the whole journey. I’m proud of the many years of organic growth to becoming one of the largest and fastest growing transportation equipment lessors in the United States.

Challenges

Biggest challenge facing your industry today?

One of the biggest challenges is around customer choice and customer expectations. Today, consumers want to have a product in their hand, yesterday, with a click of a button. That sense of urgency impacts everything we do. The challenge is keeping up with the velocity and pace of change. Our challenge is, “What can Milestone do to help our customers keep up with that velocity?”

What keeps you up at night?

How to tackle employee shortages and trying to get young people excited about the industry.

Hard to get a smart college grad to get excited about this space. We’re losing a lot of experience, knowledge-based in the business.

Outlook

What does the future hold for Milestone Trailer Leasing? What things are you excited about?

Back to these ideas of flexibility and being creative problem solvers – for me personally and for the company DNA, it’s about the love of solving pain points and solving problems for our customer. We are continually expanding our knowledge around finding solutions in trailer leasing, especially with how quickly things are changing in transportation.

Personal Story

What is a great story about Milestone Trailer Leasing that you love to share?

It’s related to how far we come. One story has to do with one of the first big acquisitions we worked on as a young company. They asked us about our net worth. It was $1 million. They asked, “$1 billion?” And we said, “No, $1 million.” It was kind of comical because it showed what a small potato we were at the time. And now here we are, close to a $1 billion company.