Customer Success

We are Leaf.

Leaf is on a mission to upend the way companies buy and sell transportation. Every year, billions of dollars, hundreds of megatons of carbon and millions of person-hours are wasted because the companies who ship goods and the companies who carry them aren’t upfront about their needs and abilities. Our platform finds ways for buyers and sellers to contract binding commitments for plannable and predictable freight and allows those contracts to be traded when needs change. In time, Leaf will become the hub through which the trillion-dollar American freight market is managed.

We are a team of experienced, smart, and mildly disagreeable troublemakers who like taking on unreasonably big challenges; we know how to build things, we’ve lived what’s broken in this industry, and we’re looking for bright, ambitious people to help us drag the transportation world kicking and screaming into the 21st century.

What does the Customer Success team member do?.

The customer success team works closely together to on-board new customers, address any concerns that arise, and ensure a growing, long-term relationship. As a member of the Customer Success team you will:

  • Work with others at Leaf to identify and engage prospective and current member companies
  • Help qualify new leads
  • Engage with analytics and data science colleagues to identify compelling, customer-specific opportunities
  • Engage key customer personnel through the on-boarding process
  • Manage customer relationships to ensure mutual success
  • Help to build both long-term customer relationships and early momentum to continue Leaf’s rapid growth.

Who makes a great Customer Success team member?.

You should be fanatical to the point of unreason about delivering real, measurable value to our customers … and making sure that they appreciate it. Know when to be a bull in a china shop, and when to kiss babies. Have some stories, and some scars to show for it.

Be able to create polished materials for customers, and deliver them with panache.

Be willing to work with people you disagree with; be eager for criticism, and constantly searching for ways to do what you do better. Never be content with things the way they are, but don’t let the quest for something perfect prevent you doing what’s good enough.

Have a sense of humor and be prepared to use it liberally.

It’s helpful if you have:

  • Significant experience around the buying, selling and management transportation (particularly truckload)
  • Proven track record of excellent performance, entrepreneurial initiative and leadership
  • Ability to plan and manage at a strategic level, while executing at an operational level
  • Strong analytical, project leadership and communication skills
  • Excellent software skills including spreadsheets, database management and presentations
  • Exceptional track record of developing and executing operational plans, providing personal leadership through example
  • Ability to work both self-directed and collaboratively to deliver results in a fast paced, startup environment
  • Prior experience in transportation management, operations, or consulting preferred
  • Unbelievably positive attitude, sense of humor and/or thick skin
  • Consummate team player, able to wear multiple hats, and assist team members when needed

Who doesn't?.

What we’re trying to do is hard, because we’re asking for big changes from people who are usually very comfortable doing things the way they’ve always been done. There is a lot of frustration, and it’s easy to put a lot of work into something that doesn’t bear fruit. But we’re here to put a big dent in a gigantic industry, something we’ll all be proud of a decade from now.

We’re also a startup. Priorities change all the time, something’s always on fire, and there’s twice as much work to do as hands to do it. Its uncomfortable, new challenges surface constantly, and that means it’s up to you to manage how you spend your time in the midst of conflicting priorities.

We’re well-funded, with advisors and investors who’ve built legendary companies. But we’re also deploying that capital aggressively, so you should expect uncertainty and discomfort.

If the above sounds daunting, you’re a perfectly sound and reasonable person who probably won’t fit in at Leaf. If this strikes you as an exhilarating milieu, well, let’s talk.


Leaf offers a very comprehensive compensation package including competitive base salary, variable compensation and health benefits.

Leaf Logistics is an equal-opportunity employer and we welcome applicants from all backgrounds. If you’re a passionate team player who wants to have an outsized impact on a diverse and dynamic team, we’d love to hear from you!