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The Sales Representative will prospect new customers, manage existing client relationships, and refine sales skills while collaborating with the operations and product teams.

The role involves prospecting new business through outreach, managing client relationships, guiding integration processes, and enhancing sales skills and product knowledge.

Leads Loadsmart’s global enterprise sales organization, partnering with the CEO and board on go-to-market strategy, forecasts, unit economics, and revenue performance. The role manages sales leaders and senior account executives, drives enterprise outbound motions, coaches complex deals, improves pipeline and forecasting discipline, supports international expansion and commercial integration, and aligns Sales with RevOps, Product, Marketing, and Customer Success. Requires extensive B2B enterprise SaaS leadership experience and Chicago-based, on-site collaboration.

Own a portfolio of SaaS customers across onboarding, enablement, adoption, renewals, upselling, and cross-selling. Build account plans tied to customer priorities, ROI, and growth goals; conduct QBRs and executive engagements; develop multi-threaded relationships; identify risks and opportunities; coordinate issue resolution; and gather customer feedback. The role requires strong communication, technical aptitude, data interpretation, influence, and customer-facing account management experience.

Research target distribution and warehouse accounts, identify decision-makers, conduct high-volume outbound outreach, qualify leads, document account insights in Salesforce, and schedule meetings for enterprise account executives. The role also requires articulating Loadsmart’s SaaS solutions, developing industry and competitive knowledge, refining prospecting messaging, and collaborating with sales teammates to achieve growth goals.

Build and deploy AI-driven automations, agents, integrations, and workflows for logistics clients. Conduct operational discovery, integrate with TMS, WMS, and ERP systems, tune prompts and voice or transcription models, debug production issues, and translate recurring customer needs into reusable platform capabilities. The role requires rapid software delivery, direct collaboration with nontechnical stakeholders, and travel to client engagements and the Chicago office.

Own paid acquisition across three B2B SaaS products, managing account-based programs, Google Ads and LinkedIn campaigns, landing pages, tracking, A/B testing, funnel optimization, budget allocation, forecasting, and executive performance reporting. The role requires hands-on ownership of pipeline measurement from impressions through closed-won revenue, including Salesforce integration, offline conversions, and lead-source governance.

Lead and develop a team of Account Sales Representatives focused on acquiring, onboarding, and retaining SMB to mid-market shippers. Drive high-volume outreach, support pricing and negotiations, assist in lead generation and cross-selling, run performance reviews, and collaborate cross-functionally to meet aggressive sales targets.

Perform high-volume outbound prospecting to research and engage warehouse and distribution decision-makers, book qualified meetings for Account Executives, communicate the value of Loadsmart's Dock & Yard SaaS, craft outbound messaging, and develop SaaS sales skills within a performance-driven team.

Prospect and prioritize warehouse and distribution targets, conduct high-volume outbound outreach (phone, email, social) to senior executives, book qualified intro meetings for Account Executives, communicate Loadsmart's digital solutions, craft compelling outbound messaging, and develop SaaS sales skills while contributing to a high-performance sales culture.