Director of Sales, Automotive

Flexport•Chicago, IL

2h•$167,000 - $180,000

About The Position

We are scaling our dedicated Automotive practice, and we are looking for the person who will lead it. This is a founding commercial role. You will start as a team of one, owning the full sales motion end-to-end, and you will build the team around you as the practice grows. You will define how Flexport expands our work with OEMs, Tier 1 and Tier 2 suppliers, EV battery manufacturers, and the broader automotive ecosystem. You will set the playbook, win marquee accounts, and hire the people who scale what you build. Reporting directly to the General Manager, you will operate with a high degree of autonomy and direct access to executive leadership. This role features a 50/50 compensation model (Base + Uncapped bonus), designed for strong leaders who take bets on themselves. Uncapped accelerators, equity grants, and comprehensive benefits.

Requirements

10+ years of overall professional experience, including direct experience selling complex, high-value logistics or supply chain solutions to Fortune 500 customers.
Deep familiarity with the automotive ecosystem—OEMs, Tier 1/Tier 2 suppliers, EV manufacturers, or automotive aftermarket—either through direct sales, account management, or operational roles.
A demonstrated track record as a top-performing individual contributor and, ideally, early-stage team builder: you know what it takes to close, and you know how to build a team that closes.
The instincts and resilience to operate as a team of one while building toward scale.
Strong consultative selling skills, with the ability to navigate complex, multi-stakeholder deals involving procurement, supply chain, logistics, and executive leadership.
Excellent analytical and commercial judgment: you can build and manage a pipeline, forecast accurately, and make strategic tradeoffs.
Exceptional communication skills and the ability to earn trust at every level, from AE to C-suite.

Responsibilities

Own the full commercial motion for Flexport's Automotive practice: from pipeline generation through close and expansion.
Build, inspire, and ultimately lead a high-performing sales team as the practice scales, including hiring, onboarding, coaching, and developing Account Executives.
Define and execute a go-to-market strategy targeting OEMs, Tier 1 and Tier 2 suppliers, EV battery and component manufacturers, and aftermarket distributors across North America.
Establish and drive specific, targeted revenue goals and quotas; monitor and manage key performance metrics to ensure consistent performance.
Partner closely with Flexport's customs, operations, and product teams to design and deliver solutions for complex automotive supply chains.
Represent Flexport externally as a subject-matter authority in automotive logistics: at industry events, in RFP processes, and in senior customer conversations.
Take an entrepreneurial approach: you are building something new inside a company with global scale, and you will bring both the vision and the execution.