--- title: 'Senior Sales Executive, Freight Forwarder Growth at Cargomatic' canonical: 'https://feeny.ai/job/senior-sales-executive-freight-forwarder-growth-cargomatic-chicago-wy3ngfbq7br4' type: 'job' last_seen: '2026-09-07' --- # Senior Sales Executive, Freight Forwarder Growth at Cargomatic - **Company:** Cargomatic - **Location:** Chicago, IL - **Posted:** 2026-02-23 - **Last confirmed live:** 2026-09-07 - **Apply:** https://job-boards.greenhouse.io/cargomatic/jobs/5123591008 ## Job description 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. ## About Cargomatic ## Company Overview - **One-liner**: Cargomatic operates the largest digital marketplace for local trucking, connecting shippers with a network of over 35,000 professional drivers to streamline local freight and drayage. - **Entity Type**: Private - **Headquarters**: Long Beach, California, USA - **Founded**: 2013 - **Founders**: Not publicly disclosed ## Core Business - **Primary industry**: Logistics & freight technology (third-party logistics / 3PL) - **Target customers**: B2B – shippers, importers, retailers, and carriers needing local, regional, or national freight solutions (LTL, FTL, drayage, intermodal, white-glove delivery) - **Mission/purpose**: “Change the way things move” by solving complex, real-world supply chain problems through innovation and technology ## Products & Services - **Digital Freight Marketplace**: AI-enabled platform that matches cargo space and drivers to shippers in real time, creating capacity on demand. - **Less‑Than‑Truckload (LTL)**: Smart routing and bundling technology to consolidate loads from multiple shippers for efficiency and cost savings. - **Full‑Truckload (FTL)**: On‑demand and scheduled full‑truckload services for local, regional, and national hauling. - **Drayage**: Port and rail‑ramp services covering the top 20 ports in the continental US. - **Intermodal**: One‑stop solution connecting air, ground, rail, and sea shipments. - **White‑Glove / Final Mile**: In‑home delivery and direct‑to‑consumer shipping with branded, high‑touch service. - **API Integration**: Seamless API for embedding Cargomatic’s marketplace into third‑party platforms. - **Storage / Yard Management**: Additional warehousing and yard services. ## Market Standing - **Valuation / Market Cap**: Not publicly disclosed - **Key Metric**: Total headcount of 453 employees (as of 2025); network of 35,000+ trucks across 50+ markets; trusted by 19 of the top 20 importers. - **Notable Investors / Partners**: Not publicly listed; leadership team comprises executives with 150+ years of combined supply chain experience. - **Growth Signals**: Named to Built In’s Best Places to Work for 2025; rapidly expanding team with multiple open roles across engineering, sales, operations, and product; continuous investment in AI‑enabled platform capabilities. ## Competitive Advantages - **Largest automated marketplace** for local freight in the US, providing unmatched capacity and coverage. - **Proprietary AI‑enabled platform** using real‑time location data to optimize load matching and routing. - **True one‑stop shop** – one provider for LTL, FTL, drayage, intermodal, white‑glove, and yard management, managed through a single technology platform. - **Subsidiary‑owned assets** combined with a vast network of owner‑operators and fleets ensures reliability and flexibility. ## Strategic Focus - Continuing to expand technology platform and automation to reduce friction in fragmented freight processes. - Deepening relationships with top importers and expanding into additional U.S. markets. - Enhancing API and integration capabilities to embed Cargomatic into customer supply chains. - Growing the team across engineering, product, sales, and operations to support scaling. ## Why Work Here - **Culture**: Values include transparency, accountability, modesty, partnership, and intellectual curiosity. Described as a people‑first environment where employees thrive on solving complex problems. - **Work policy**: OnSite workspace – employees within a 40‑minute commute of hub offices (Long Beach, San Francisco, Chicago, Dayton NJ) are required to work onsite unless their role is designated as remote. - **Benefits**: Competitive salary, 401K match, flexible PTO, company‑sponsored life insurance, and a strong benefits package. - **Recognition**: Named a Built In Best Places to Work for 2025. - **Engineering culture**: Uses modern tech stack (GitHub, CRM tools); emphasis on innovation and real‑world impact in logistics. ## Sources 1. [Cargomatic Website](https://cargomatic.com/) 2. [Cargomatic Careers Page](https://cargomatic.com/about/careers/) 3. [Cargomatic Leadership Page](https://cargomatic.com/about/leadership/) 4. [Built In Company Profile](https://builtin.com/company/cargomatic) 5. [LinkedIn Company Page](https://www.linkedin.com/company/cargomatic) ## Other roles at Cargomatic - [Yard Manager](https://feeny.ai/job/yard-manager-cargomatic-jacksonville-zswhez5x7xwn) — Jacksonville, FL - [Yard Hostler Driver](https://feeny.ai/job/yard-hostler-driver-cargomatic-moreno-valley-ca-prince-george-gex1hjhty9v8) — Moreno Valley CA Prince George, VA - [LTL & Truckload Specialist](https://feeny.ai/job/ltl-truckload-specialist-cargomatic-long-beach-ca-san-fransisco-ca-dayton-nj-w38zqd3gp8va) — Long Beach CA San Fransisco CA Dayton NJ Norfolk, VA - [Director, LTL & Truckload](https://feeny.ai/job/director-ltl-truckload-cargomatic-san-fransisco-ca-long-beach-ca-dayton-nj-6rz0cc1m4y4x) — San Fransisco CA Long Beach CA Dayton NJ Norfolk, VA - [AI Engineer](https://feeny.ai/job/ai-engineer-cargomatic-san-francisco-wgewsavw6hh3) — San Francisco, CA - [SMB Sales Manager — Drayage Transportation](https://feeny.ai/job/smb-sales-manager-drayage-transportation-cargomatic-united-states-h9kv4x5z8t74) — United States - [Pricing Analyst – Drayage](https://feeny.ai/job/pricing-analyst-drayage-cargomatic-long-beach-3tsbbhxfvexd) — Long Beach, CA - [Operations Coordinator](https://feeny.ai/job/operations-coordinator-cargomatic-bloomington-48455xmww8sj) — Bloomington, CA - [Safety and Compliance Manager](https://feeny.ai/job/safety-and-compliance-manager-cargomatic-dallas-bzhbwdv5sbn0) — Dallas, TX - [Port and Rail Dispatch Manager - Savannah](https://feeny.ai/job/port-and-rail-dispatch-manager-savannah-cargomatic-savannah-thyfaqy323b5) — Savannah, GA