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Senior Sales Executive, Freight Forwarder Growth

Clutch Canada, Chicago, Illinois, United States, 60290

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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.

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