New

Director of Sales, Automotive

Chicago, Illinois, United States

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 $10T 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. We 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.

The Opportunity

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.

Why This Role Is Different

The automotive logistics market is not a standard freight problem. A production line stoppage costs OEMs $50,000–$100,000 per minute in lost output—meaning a single missing part can trigger a crisis that no amount of expediting fully recovers. The industry is simultaneously navigating the most complex tariff environment in a generation: USMCA rules of origin require tracking Regional Value Content across multi-tier supplier networks, while Section 232 tariffs and ongoing trade policy volatility create constant, unpredictable duty exposure.

Flexport has built the capabilities this market demands:

Customs expertise built for automotive complexity. Our AI-powered customs engine error-checks 100% of filings before submission—achieving a 0.2% error rate, roughly ten times better than the industry average. For OEMs and Tier 1s navigating USMCA rules of origin, HTS classification across thousands of part numbers, and volatile Section 232 exposure, this is a true competitive moat.
$900M+ saved in tariff exposure for customers over five years—through duty optimization, FTZ utilization, and first-entry-free strategies that protect margin on high-volume parts flows.
Real-time digital control tower with proactive exception management—giving customers and their supply chain teams milestone-level visibility before a disruption reaches the production floor.
Mexico cross-border expertise. As nearshoring reshapes automotive manufacturing, our US-Mexico corridor capabilities—customs brokerage, cross-border trucking, and bonded warehouse solutions—are increasingly central to how OEMs and Tier 1s are reconfiguring their supply chains.

You Will

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.

You Should Have

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.

The range displayed on each job posting reflects the minimum and maximum target for new hire base salary for the position in the posting's respective region. Our salary ranges are determined by role, level, and location. Within the range displayed, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education and / or training. Base salary is just one part of our total rewards package at Flexport, which also includes bonus, equity, and comprehensive benefit offerings such as medical, dental, and flexible time off. The US base salary range for this position (this does not include bonus, equity and benefits):

$167,000 - $180,000 USD

Commitment to Equal Opportunity

At Flexport, our ability to fulfill our mission of making global commerce easy and accessible relies on having a diverse, dedicated and engaged workforce. 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.

Global Data Privacy Notice for Job Candidates and Applicants

Depending on your location, the General Data Protection Regulation (GDPR) and California Consumer Privacy Act (CCPA) may regulate the way we manage the data of job applicants. By submitting your application, you are agreeing to our use and processing of your data as required. Please see our Privacy Notice available at www.flexport.com/privacy for additional information.

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