Top Tech Jobs & Startup Jobs in Chicago, IL

Generate and qualify sales opportunities through cold outreach, inbound lead response, discovery calls, and relationship building with trucking carriers. Collaborate with Account Executives on outreach and lead handoffs, develop expertise in Toro’s transportation management software and industry, understand competitors, and consistently achieve qualified-opportunity and sourced-ARR quotas. This is an in-office Chicago role designed for upcoming graduates beginning careers in software sales.

Lead and grow an outbound SDR team to generate pipeline, hire and coach reps, align SDR efforts with sales goals, and drive measurable results while fostering a positive, performance-driven culture in Toro TMS's Chicago HQ.

Lead a hands-on engineering team building and shipping features for a modern trucking transportation management system. Partner with Product and Design to shape roadmaps, contribute to Ruby on Rails and React development, mentor engineers, maintain engineering quality, understand customer workflows, and deliver improvements quickly in a fully remote environment.

Build and ship web-based transportation management software for trucking customers. Collaborate with product, UX, and engineering teammates to understand user workflows, solve domain problems, deliver features rapidly, and maintain an effective balance between quality and velocity. The role requires proactive ownership, strong communication, frequent collaboration, and willingness to learn the trucking industry and engage with customers.

The Mid-Market Account Executive will manage the full sales cycle, meet sales quotas, build client relationships, conduct demos, and travel as needed.