Senior Sales Executive, Freight Forwarder Growth

Cargomatic; Chicago (IL); On-site; USD 150,000 - 185,000; Full time

Benefits offered by this job

Competitive base salary + performance-based incentive

Medical, dental, and vision insurance

401(k) plan with company match

Generous paid time off

Remote-friendly work environment

Job summary

A logistics and transportation provider is seeking a Senior Sales Executive in Chicago to drive new customer acquisition and expand existing accounts. The role focuses on winning new freight forwarder accounts and managing the full sales lifecycle. Candidates should have over 5 years of B2B sales experience in logistics and proven success in prospecting and closing deals. The position offers a competitive salary with total earnings up to $185,000. Benefits include medical insurance and a flexible working environment.

Qualifications

• 5+ years of B2B sales experience in logistics, transportation, or supply chain.
• Proven success in outbound prospecting and closing new business.
• Demonstrated ability to expand wallet-share within existing accounts.

Responsibilities

• Prospect, qualify, and close new freight forwarder accounts.
• Drive volume and gross profit growth within current accounts.
• Partner with operations and customer teams to ensure seamless onboarding.

Skills

B2B sales experience

Outbound prospecting success

Strong discovery skills

Negotiation skills

CRM proficiency

Tools

CRM

Job description

Senior Sales Executive / Freight Forwarder Growth

Freight Forwarder Growth (New Logo + Existing Account Expansion)
Location: Chicago, IL
Reports To: Mike Anderson
Compensation: Total on-target earnings of up to $185,000 annually (base salary plus bonus potential)

About ITG Trans

ITG Trans, powered by Cargomatic, is a fast-growing logistics and transportation provider delivering reliable, flexible freight solutions nationwide. We partner with freight forwarders across multi-branch networks to provide scalable, high-performance transportation solutions.

As we enter our next phase of growth, we are investing in top-tier sales talent to accelerate new customer acquisition and expand share-of-wallet within our existing freight forwarder portfolio.

The Opportunity

We are seeking a high-performing sales leader who thrives in a hunter + farmer role. This position is responsible for winning new freight forwarder accounts while aggressively expanding volume and profitability within existing forwarder relationships. You will drive branch-by-branch adoption across forwarder networks and own the full sales lifecycle — from prospecting and pipeline creation through onboarding and account expansion — partnering closely with operations and customer support to ensure long-term success.

What You’ll Do

New Account Development (Hunting)

• Prospect, qualify, and close new freight forwarder accounts aligned to our ideal customer profile

• Build and manage a strong outbound pipeline via calls, email, networking, and referrals

• Conduct consultative discovery to understand operational needs and buying processes

• Develop proposals, pricing strategies, and service plans that drive profitable growth

• Own the sales process from first contact through first shipment stabilization

Existing Customer Expansion (Growth Focus)

• Drive volume and gross profit growth within current freight forwarder accounts

• Map forwarder organizations and identify additional branch decision-makers

• Onboard additional branches and expand adoption across forwarder networks

• Expand share-of-wallet by adding lanes, services, and repeat shipment programs

• Lead structured account growth plans with clear targets and next steps

• Coordinate internally to remove obstacles and accelerate expansion

Sales Execution & Collaboration

• Partner with operations and customer teams to ensure seamless onboarding

• Maintain clear communication during implementation and issue resolution

• Manage pipeline, forecasting, and account planning within CRM

• Stay informed on market trends, competitive positioning, and customer needs

What Success Looks Like

• Measurable growth in volume and gross profit across existing forwarder accounts

• Consistent onboarding of new branches within current customers

• Increased share-of-wallet through additional lanes and services

• Closed-won new forwarder accounts that become active shippers

• Accurate forecasting and a healthy, well-managed pipeline

What You Bring

• 5+ years of B2B sales experience in logistics, transportation, or supply chain

• Proven success in outbound prospecting and closing new business

• Experience selling into freight forwarders or building forwarder relationships

• Demonstrated ability to expand wallet-share within existing accounts

• Strong discovery, presentation, and negotiation skills

• Experience managing multi-stakeholder deals

• CRM proficiency and disciplined pipeline management

• Comfortable operating in a performance-driven environment

Preferred

• Existing relationships in the freight forwarder ecosystem

• Experience selling freight forwarding or LTL solutions

• Experience with mid-market and enterprise accounts

• Familiarity with structured sales methodologies (MEDDICC, SPICED, Challenger, etc.)

Benefits & Perks

At Cargomatic, we believe great people do their best work when they’re supported — professionally and personally. We offer a competitive benefits package designed to promote health, flexibility, and long-term growth, including:

• Competitive base salary + performance-based incentive compensation

• Medical, dental, and vision insurance with multiple plan options

• 401(k) retirement plan with company match

• Generous paid time off (PTO), including holidays

• Remote-friendly work environment with flexibility for field-based roles

• Career growth opportunities within a fast-growing logistics technology company

• Collaborative, entrepreneurial culture where performance and accountability are valued

• Tools and resources to support sales success (CRM, enablement, operational support)

Why Join ITG Trans

This role is central to ITG’s next phase of growth. You’ll have the opportunity to build meaningful forwarder relationships, expand multi-branch networks, and directly impact revenue growth in a high-visibility role within a growing logistics platform powered by Cargomatic.

If you’re a driven sales professional who excels at both winning new business and expanding strategic accounts, we’d love to connect.