Top Tech Jobs & Startup Jobs

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.

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.

Owns go-to-market campaigns, product messaging, positioning, sales enablement, customer proof, events, buyer research, and cross-functional marketing initiatives for an AI-enabled B2B SaaS logistics product. The role develops competitive materials, maintains consistent messaging across channels, supports sales and customer success, manages review programs and case studies, and translates complex product features into clear customer value.

Build and optimize AI-driven outbound programs across account strategy, scoring, enrichment, contact coverage, Salesforce data quality, and Salesloft sequences. Analyze win/loss and Gong data, improve pipeline performance, manage SDR scorecards, test new plays, and introduce revenue-focused tools and workflows. The role partners closely with sales leadership and requires hands-on expertise in RevOps, GTM systems, automation, and outbound strategy.

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.

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.