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Posted 26 Aug 2026 (71 days ago) · Job 9275 · Read from the employer's Greenhouse board, last checked 5 Nov 2026, 16:26 UTC

Mid-market Sales Manager

Flexport · Chicago, Illinois

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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’re looking for a pragmatic, growth-minded Sales Leader with a proven history of driving success to guide our Mid-Market Sales Team in Chicago, IL. In this role, you’ll coach and develop Account Executive, building high-performing, inclusive teams to achieve company goals for volume growth and net revenue. You’ll play a critical part in developing talent for progression and promotion within our fast-growing organization. Reporting directly to our General Manager, you’ll collaborate closely with the Mid-Market Leadership Team to deliver key outcomes. This role features a 50/50 compensation model (Base + Uncapped bonus), designed for strong leaders to effectively maximize their earnings through a heavily incentivized sales program.

You will:

  • Build, inspire, and lead strong sales teams that consistently meet and exceed targets.
  • Provide inclusive leadership and clear direction to a high-performance team, including hiring, training, and development.
  • Establish and drive specific, targeted goals and quotas to expand and accelerate revenue opportunities.
  • Create, monitor, and manage key performance metrics to drive performance and results.
  • Identify and implement innovative strategies to enhance team performance and growth.
  • Implement and continually refine best practices to support consistent, consultative sales and client success processes.
  • Champion and evolve an effective go-to-market strategy aligned with company objectives.
  • Take an entrepreneurial and collaborative approach, working closely with the broader Leadership Team to achieve results.

You should have: 

  • 7+ years of overall professional experience, including experience scaling and managing client-facing teams in a dynamic environment.
  • Demonstrated experience as a high-performing sales executive.
  • Proven track record of leading teams to achieve quota and growth targets.
  • Strong, inclusive leadership and people management skills.
  • Ability to manage a wide portfolio of responsibilities independently and to adapt quickly to changing circumstances.
  • Excellent analytical, numerical, and strategic skills.
  • Exceptional communication skills with the ability to build trust across all levels within and outside the organization.

#LI-onsite

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):
$110,000—$137,000 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

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