Job Overview
Location
Chicago, Illinois
Job Type
Full-time
Category
Sales
Date Posted
May 21, 2026
Full Job Description
đź“‹ Description
- • VP of Sales role at CXT Software, a leader in Transportation Management Systems (TMS) for last-mile and courier operations, offering a rare opportunity to shape a newly unified sales organization post-merger and drive revenue growth, go-to-market execution, and market leadership.
- • Day-to-day responsibilities include developing and executing a comprehensive sales strategy, leading as a player-coach on complex enterprise deals, driving cross-functional alignment with Marketing, Customer Success, and Product, building and scaling the sales organization from the ground up, defining sales process discipline, owning forecasting accuracy, representing the company publicly at events, driving expansion in key verticals, developing strategic partnerships, owning the full sales cycle, monitoring market trends, and fostering a high-accountability, data-driven culture.
- • The team is part of CXTSolutions LLC, formed from the merger of CXT Software and e-Courier, creating the largest TMS purpose-built for last-mile and courier operations in North America, with a mission to innovate and expand through acquisition while serving courier, last-mile, and healthcare logistics companies.
- • In this role, the individual can learn to lead a scaled sales organization in a high-growth SaaS environment, master complex enterprise sales in logistics technology, refine forecasting and pipeline management using MEDDPICC/SPICED frameworks, build strategic partnerships, and leave a lasting impact on a category-leading TMS platform through innovation and leadership.
🎯 Requirements
- • 15+ years of progressive experience in B2B SaaS sales, including at least 10 years in senior sales leadership roles with direct ownership of multi-million-dollar revenue targets.
- • 5+ years of direct experience selling Transportation Management Systems (TMS) or last-mile / logistics technology.
- • Proven track record of forecasting accuracy through rigorous pipeline inspection, predictable stage-progression criteria, and standardized qualification frameworks (MEDDPICC, SPICED, or similar) for reliable reporting.
- • Demonstrated experience building and scaling sales organizations from the ground up using repeatable frameworks and playbooks.
- • Background scaling mid-market to enterprise SaaS companies.
🏖️ Benefits
- • 100% Remote and Global: Enjoy the freedom to live your best life from anywhere in the world.
- • Flexible Work Environment: Work at times that suit you best. We prioritize results and customer satisfaction over rigid schedules.
- • Dedicated Growth Path: Receive consistent, meaningful feedback and support tailored to help you achieve your personal career goals.
- • Access to Leading Tools and Technology: Enhance your skills with the latest tools, playbooks, and technology.
- • Engaging Community Activities: Participate in coffee chats, happy hours, cooking classes, book clubs, and more!
Skills & Technologies
About CXTSolutions LLC
CXTSolutions LLC, operating as CXT Software, develops logistics and courier management software for same-day, last-mile, and distribution operations. Its platforms automate dispatch, routing, barcode scanning, proof-of-delivery, and customer communication for carriers, pharmacies, retailers, and wholesalers, integrating with e-commerce, ERP, and accounting systems. The company provides cloud and on-premise solutions plus mobile driver apps, serving North American and Australian markets from its Scottsdale, Arizona headquarters since 1999.
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