Director, SaaS Sales

🕒 Yesterday

🌽 Illinois – Remote

🌽 Illinois – Remote

💵 $157k - $200k / year

⏰ Full Time

🔴 Lead

🤑 Sales

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Loadsmart

WebsiteLinkedInAll Job Openings

501 - 1000 employees

🚗 Transport

☁️ SaaS

🤖 Artificial Intelligence

💰 $200M Series D on 2022-02

Transport • SaaS • Artificial Intelligence

Loadsmart is a company that specializes in providing advanced freight and logistics solutions. They offer a range of services including managed transportation, freight planning, and execution, as well as multimodal shipping capabilities such as FTL, LTL, PTL, and drayage. Loadsmart leverages technology and artificial intelligence through tools like ShipperGuide TMS and FreightIntel AI to optimize freight operations, reduce costs, and enhance efficiency. Their solutions include a robust Transportation Management System, dock scheduling software, and visibility tools for yards and assets. Loadsmart also offers digital brokerage services and tools to optimize carrier networks and fleet operations. They are committed to transforming logistics through innovative technology and real-time data insights.

📋 Description

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

🎯 Requirements

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

🏖️ Benefits

• Competitive base salaries - we believe in rewarding top talent • Extremely competitive Equity package - become a shareholder in our company! • Loadie Time Off - PTO and sick days without a limit • Comprehensive Medical, Dental, and Vision insurance plans • 401k Match