SMB Sales Manager — Drayage Transportation

Cargomatic•Chicago, IL

1d•$150,000•Remote

About The Position

The Sales Manager, SMB is responsible for driving revenue growth across a high-velocity segment of small and mid-sized customers. This role will lead, coach, and develop a team of Account Executives while also contributing directly to pipeline development and key deals. This is a hands-on leadership role requiring a balance of strategic thinking and tactical execution. The ideal candidate has a strong background in freight, logistics, or transportation sales and thrives in a performance-driven environment.

Requirements

5+ years of sales experience in freight, logistics, trucking, or supply chain
2+ years of experience leading or mentoring sales teams preferred
Proven track record of meeting or exceeding revenue targets
Strong understanding of SMB sales motion and high-velocity sales cycles
Experience managing pipeline, forecasting, and CRM systems (Salesforce preferred)
Excellent communication, negotiation, and relationship-building skills
Ability to operate in a fast-paced, growth-oriented environment
Highly organized, data-driven, and results-oriented

Nice To Haves

Experience in drayage, intermodal, or local trucking markets
Existing relationships with shippers, brokers, or logistics providers
Background in scaling SMB or mid-market sales teams
Experience in a technology-enabled logistics platform

Responsibilities

Hire, onboard, and develop a team of SMB Account Executives
Set clear performance expectations and manage team to quota attainment
Coach reps on pipeline generation, deal strategy, and closing techniques
Foster a high-performance, accountable, and collaborative sales culture
Own team pipeline health, forecasting accuracy, and revenue performance
Drive outbound and inbound sales strategies to generate new business
Partner with marketing to optimize lead flow and conversion rates
Support strategic deals and remove blockers to accelerate close cycles
Build and maintain relationships with shippers, freight brokers, and logistics partners
Develop a deep understanding of customer needs across SMB segments
Stay informed on market trends, pricing dynamics, and competitive landscape
Represent Cargomatic at industry events and customer meetings
Partner closely with operations to ensure service delivery and customer satisfaction
Align with pricing and finance teams on deal structure and profitability
Collaborate with leadership on go-to-market strategy and sales process improvements
Track and report on key sales metrics including pipeline, conversion rates, and revenue
Ensure CRM accuracy and disciplined sales processes across the team
Identify opportunities to improve sales efficiency, tooling, and workflows