Come build the future

7percent Ventures
7percent Ventures

Senior Director, Truckload Platform Sales



Sales & Business Development
Chicago, IL, USA
Posted on Friday, June 7, 2024

About Flexport:

At Flexport, we believe global trade can move the human race forward. That’s why it’s our mission to make global commerce so easy there will be more of it. We’re shaping the future of a $8.6T industry with solutions powered by innovative technology and exceptional people. Today, companies of all sizes—from emerging brands to Fortune 500s—use Flexport technology to move more than $19B of merchandise across 112 countries a year.

The recent global supply chain crisis has put Flexport center stage as we continue to play a pivotal role in how goods move around the world. At a valuation of $8 billion, we’re experiencing record growth and are proud to have the support of the best investors in the game who believe in our mission, solutions and people. Ready to tackle global challenges that impact business, society, and the environment? Come join us.

Help win new business

Operating at the intersection of logistics and tech has allowed Flexport to develop a unique value proposition that customers all over the globe love, resulting in exponential growth over the last 9 years. As part of our mission to make global trade easy for everyone, we are continuing to grow our sales organization.

The opportunity:

We are seeking a highly motivated, seasoned and strategic leader to join our growing team as the Senior Director of Truckload Sales. Through the relaunch of the Convoy Platform, we are scaling our business around market leading technology. We need a leader who is motivated by driving early stage growth, building a new market, and the uncapped potential that comes with that. We have the best platform, with over $1B invested in building out the technology, and we’re building the best sales team to sell it. This is a senior commercial leadership role responsible for the business development, revenue growth, and customer retention across Flexport Freight and Convoy Platform. You will be responsible for driving sales excellence across our truckload business, ensuring we consistently achieve superior topline revenue and net revenue results. You will oversee a team of talented individuals, develop and implement strategies to optimize performance, improve customer relationships, and drive profitable growth. This is an exciting opportunity for a passionate and results-oriented leader to play a pivotal role in shaping the future of our company.

You will be:

  • Develop and implement a data-driven sales strategy to achieve ambitious revenue goals
  • Lead and coach a team of enterprise sellers to exceed their individual and team quotas
  • Develop and maintain strong relationships with key enterprise customers and third-party partners
  • Oversee the entire sales process, from lead generation and qualification to proposal development, negotiation, and closing
  • Analyze sales data and identify trends to optimize sales performance
  • Develop and implement sales training programs to continuously improve the skills and knowledge of the sales team
  • Manage and forecast sales pipeline to ensure predictable and consistent revenue growth
  • Partner with marketing, engineering, and other departments to ensure alignment and support for sales initiatives
  • Develop and implement sales compensation plans that incentivize and motivate the sales team

You should have:

  • 15+ years of experience in transportation and logistics, with a proven track record of success in truckload sales, with experience selling solutions as well as transactional truckload
  • Strong understanding of the digital brokerage landscape and its commercial nuances.
  • Excellent leadership and communication skills, with the ability to motivate and inspire a team.
  • Proven ability to develop and implement effective strategies, with a data-driven approach to decision-making.
  • Deep understanding of customer & broker relationships and negotiation techniques.
  • Proficiency in transportation management systems (TMS) and other relevant technologies.
  • Demonstrated ability to manage the sales process on large scale transportation solutions with both technology and operational elements.
  • Proven track record in continuous improvement projects and large scale implementations
  • Comfortable in managing people remotely across multiple geographies


At Flexport, our ability to fulfill our mission of making global commerce easy and accessible relies on having a diverse, dedicated and engaged workforce. That is why Flexport is committed to creating and nurturing an environment where anyone can be their authentic self. All qualified applicants will receive consideration for employment regardless of race, color, religion, sex, national origin, age, physical and mental disability, health status, marital and family status, sexual orientation, gender identity and expression, military and veteran status, and any other characteristic protected by applicable law.