Director, SaaS Sales ShipperGuide

ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?

Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)!

We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.

With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.

We are seeking an experienced and strategic Director of Global Account Management to lead and grow our Account Management Team and portfolio of key enterprise clients across global markets. Reporting to the SVP of Customer Experience, this role is responsible for building and scaling a high-performing global account management organization, driving revenue retention, expansion growth, and serving as the executive voice for our customer relationships.

Job Type: (Exempt) - U.S. Only

DEPARTMENT: Customer Success

LOCATION: Chicago IL or remote, depending on location

WHAT YOU GET TO DO

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• Carry and achieve a personal annual sales quota, directly owning a pipeline of net-new and expansion opportunities across ShipperGuide
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• Actively prospect, develop, and close strategic deals, modeling best-in-class selling behaviors for the team
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• Own and manage a personal book of business, including key accounts and high-value prospects, with full accountability for forecasting and pipeline health
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• Develop and execute a unified go-to-market strategy for both ShipperGuide and OpenDock that maximizes market penetration and revenue growth
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• Drive full-funnel sales execution, from lead qualification to closing and onboarding
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• Establish repeatable sales processes and ensure consistent adoption of tools, CRM hygiene, and reporting standards
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• Partner with marketing to define and refine ICPs, messaging, and campaign strategies
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• Align with Customer Success to ensure a smooth handoff from sales to onboarding and retention initiatives
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• Collaborate with Finance on pricing strategies, discount approvals, and revenue forecasting
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• Work with the Account Management team to proactively identify and execute account growth strategies, including upsells and cross-sells
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• Work closely with Managed Transportation and Brokerage sales leadership to identify cross-sell and upsell opportunities

REQUIRED QUALIFICATIONS

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• 7+ years in SaaS TMS sales with at least 5 years in a leadership role, including direct quota-carrying responsibility at the Director level or above
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• Experience in public speaking and events
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• Proven track record of personally closing multi-million-dollar deals while simultaneously leading a team to exceed ARR targets
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• Strong operational discipline with the ability to build scalable, repeatable sales processes
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• Proven track record of leading teams to exceed multi-million-dollar ARR targets
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• Exceptional communication, negotiation, and presentation skills
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• Proficiency in Salesforce, SalesLoft, and sales analytics tools
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• Experience selling into supply chain, logistics, transportation, or similar industries
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• Experience managing multi-product sales teams or selling a platform with complementary offerings
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• Familiarity with both SMB/mid-market and enterprise SaaS sales motions
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• History of working closely with marketing and product to refine GTM strategy