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SMB Sales Manager — Drayage Transportation

Salary$150k+

LocationDowntown Chicago, United States

Work moderemote

Typefull-time

DepartmentRegional Hunters

EquityIncluded

Company size11+ people

First seen1w ago

Last seen2d ago

Here’s a polished, nationwide Greenhouse-ready posting using your sales template and aligned to the HR posting structure:

Sales Manager, Small & Medium Business (SMB)

Location: United States (Remote)

Reports To: Director of Sales

Employment Type: Full-Time

Compensation: $150,000 base salary + 20% target bonus + equity (5,000 options, subject to board approval)

About Cargomatic

Cargomatic is transforming the local trucking industry with cutting-edge technology that connects shippers and carriers in real time. Our mission is to bring transparency, efficiency, and reliability to local freight logistics. Backed by leading investors and trusted by some of the world’s largest brands, we are building a smarter, more efficient supply chain.

At Cargomatic, we value ownership, accountability, collaboration, and continuous improvement. If you thrive in a fast-paced, high-growth environment and enjoy building scalable revenue engines, we’d love to meet you.

Position Summary

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.

Key Responsibilities

Sales Leadership & Team Development

· 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

Pipeline Development & Revenue Execution

· 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

Customer & Market Engagement

· 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

Cross-Functional Collaboration

· 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

Operational Excellence & Reporting

· 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

Qualifications

· 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

Preferred Experience

· 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

Why Join Cargomatic?

We offer competitive compensation and a comprehensive benefits package, including:

· Medical, Dental, and Vision insurance

· 401(k) with company match

· Flexible Spending Accounts (FSA)

· Company-paid Life and Disability insurance

· Generous Paid Time Off and company holidays

· Paid Parental Leave

· Employee Assistance Program (EAP)

· Equity participation in a high-growth company

· Career growth opportunities in a rapidly scaling organization

· Collaborative, high-impact team environment

Legal

Cargomatic is proud to be an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace where all employees feel valued and empowered to succeed.

More roles at Cargomatic

Terminal Operations Manager (Drayage / Port Logistics)Port Dispatcher/Driver Manager - Port/Drayage Pricing Analyst – Drayage LTL & Truckload Specialist Yard Manager

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← Back

Cargomatic

SMB Sales Manager — Drayage Transportation

Salary$150k+

LocationDowntown Chicago, United States

Work moderemote

Typefull-time

DepartmentRegional Hunters

EquityIncluded

Company size11+ people

First seen1w ago

Last seen2d ago

Here’s a polished, nationwide Greenhouse-ready posting using your sales template and aligned to the HR posting structure:

Sales Manager, Small & Medium Business (SMB)

Location: United States (Remote)

Reports To: Director of Sales

Employment Type: Full-Time

Compensation: $150,000 base salary + 20% target bonus + equity (5,000 options, subject to board approval)

About Cargomatic

Position Summary

Key Responsibilities

Sales Leadership & Team Development

· 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

Pipeline Development & Revenue Execution

· 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

Customer & Market Engagement

· 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

Cross-Functional Collaboration

· 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

Operational Excellence & Reporting

· 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

Qualifications

· 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

Preferred Experience

· 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

Why Join Cargomatic?

We offer competitive compensation and a comprehensive benefits package, including:

· Medical, Dental, and Vision insurance

· 401(k) with company match

· Flexible Spending Accounts (FSA)

· Company-paid Life and Disability insurance

· Generous Paid Time Off and company holidays

· Paid Parental Leave

· Employee Assistance Program (EAP)

· Equity participation in a high-growth company

· Career growth opportunities in a rapidly scaling organization

· Collaborative, high-impact team environment

Legal

Cargomatic is proud to be an Equal Opportunity Employer. We are committed to creating a diverse and inclusive workplace where all employees feel valued and empowered to succeed.

More roles at Cargomatic

Terminal Operations Manager (Drayage / Port Logistics)Port Dispatcher/Driver Manager - Port/Drayage Pricing Analyst – Drayage LTL & Truckload Specialist Yard Manager

Seekless

Product

Find jobs Companies Pricing

Legal

Privacy Terms Cookies