Customer Success Lead

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 Lead do?.

The customer success team owns the customer relationship from on-boarding to retention. This includes support, services, adoption, advocacy, and outcomes (e.g. renewals, up-sell, etc.). The VP will be responsible for building and managing the team.

We are looking for someone who can:

  • Make our customers successful (against their will, if necessary)
  • Build, inspire, and lead a brutally powerful team
  • Define the processes through which we interact with customers
  • Reduce the amount of time and effort required to onboard customers
  • Manage the team’s activities, measure how well we’re doing, and implement strategies to improve
  • Work with our engineering and data science groups to automate and improve the efficiency of our processes

Who makes a great Customer Success Lead?.

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, deliver them with panache, and teach your team how to do the same.

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.

Knowledge of the transportation industry, especially truckload, is useful, and it’s helpful if you have:

  • Solid experience building and leading customer-facing teams
  • Ability to manage influence through persuasion, negotiation, and consensus building
  • A combined background of post-sale and sales experience
  • Strong empathy for customers and passion for revenue and growth
  • Deep understanding of value drivers in recurring revenue business models
  • An analytical and process-oriented mindset

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!