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.

Process customer contract pricing requests and manage RFPs, bids, mini-bids, and spot-pricing analyses. Maintain pipeline tracking, coordinate with sales and account management, resolve customer questions, submit final bids through third-party portals, and support improvements to the contract-pricing process. The role requires strong organization, communication, spreadsheet skills, attention to detail, and the ability to meet firm deadlines in a high-pressure environment.

Coordinate customer shipments by quoting, booking, and scheduling appointments via email, phone, or customer TMS. Collaborate with Sales and Carrier teams to optimize loads, handle high-volume scheduling, escalate challenging requests, and maintain high customer service standards in a fast-paced logistics environment.

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.

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.

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.

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.

Perform continuous manual and automated testing across web and mobile logistics products. Design edge-case, error-state, boundary-condition, regression, and exploratory tests; identify defects and write actionable reports. Maintain and extend automation frameworks using Playwright, Cypress, or Selenium, leverage Claude and other AI tools for test design and investigation, and collaborate with engineering teams in fast weekly release cycles.

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.

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.

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.