Senior Sales Executive, Freight Forwarder Growth

Senior Sales Executive / Freight Forwarder Growth

Freight Forwarder Growth (New Logo + Existing Account Expansion) Location: Chicago, IL Reports To: Allen Clifford 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.