External
On-site
SaaS
themuse
About this role
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.
Iden
Selling Motion
Sales Cycle
Mid-Market
1–6 month cycles, moderate deal complexity
Buyer Persona
C-Suite
Selling to executive decision-makers
Requirements at a Glance
Typical Day — Sales Manager
Estimates based on role type and selling motion — actual may vary by company.
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
How do you coach underperforming reps?
Template questionDescribe your forecasting methodology.
Template questionHow do you structure onboarding for new hires?
Template questionThis leadership position involves both strategic planning and hands-on coaching of the sales team.
Expect to work with recurring revenue models where customer retention is as important as acquisition.
The US market offers the highest OTE potential globally for sales professionals, with a highly competitive talent landscape.
Are you a closer?
Interested in SaaS? Build your profile to get matched with roles like this.
Explore More Sales Jobs
Similar Roles
Enterprise Account Executive - Remote
TCP Software
SMB Account Executive
Uncapped
Business Development Manager
Smart Source
Enterprise Account Executive - PNW
Pentera
Senior Account Executive (Enterprise SaaS – Pharmaceutical Manufacturing)
Vimachem
$125k–$175k
Senior Account Executive
Bridgeway Benefit Technologies
Browse More Jobs
Ready to land your next closing role?
Build your free closer profile to get matched with high-ticket sales opportunities, track applications, and showcase your track record.
Join 500+ closers already on the platform • Free forever