Jobs at Loadsmart

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.

Prospect new customers through high-volume outreach, sell freight and logistics services, manage existing accounts, negotiate contracts, support onboarding, and collaborate with operations, product, and engineering teams to improve customer value.

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.

Researches target logistics, distribution, and warehouse accounts; identifies decision-makers; conducts high-volume outreach by phone, email, and social media; qualifies leads; documents account information in Salesforce; communicates Loadsmart’s digital solutions; and schedules introductory meetings for Account Executives. Requires 1–2+ years of direct sales or lead generation experience, quota achievement, strong communication skills, and enthusiasm for collaborative entrepreneurial work.

Build and operate Loadsmart’s internal platform, ensuring reliability, scalability, cost efficiency, and operational excellence. Lead reliability initiatives across engineering squads, manage SLAs and SLOs, troubleshoot production issues, conduct root-cause analysis, support infrastructure during off-hours, and own software infrastructure projects. The role requires hands-on expertise in AWS, Kubernetes, Docker, CI/CD, infrastructure automation, Linux systems, monitoring, incident management, and scripting, alongside technical leadership and mentoring.

Lead end-to-end demand-generation for Brazil, building a full-funnel engine across SEO, paid media, events, PR, and localized content. Partner with sales to create GTM plans, generate qualified opportunities, and iterate based on performance and local market insights.