Enterprise Sales - Chicago

Bitfreighter • Chicago, IL

9d • $150,000 - $250,000 • Remote

About The Position

We're looking for a high-performing Enterprise Sales Executive to drive new logo acquisition and strategic expansion within large freight brokerages, 3PLs, and logistics organizations. This is a full-time role based in the Greater Chicago, IL area, focused on complex, consultative sales cycles — working directly with executive stakeholders to position Bitfreighter as a mission-critical integration partner. You'll own the full sales cycle from prospecting to close, identifying and closing new enterprise customers across freight and logistics — including shippers, 3PLs, and carriers. Day to day, that means managing a high-quality pipeline, running discovery calls and demos, building tailored proposals, and leading contract negotiations with key decision-makers. You'll work closely with marketing, product, and customer success to refine messaging, shape platform enhancements, and ensure a smooth handoff from sales to implementation — while nurturing executive relationships, tracking performance metrics, and representing Bitfreighter at industry events.

Requirements

• 5+ years of B2B SaaS sales experience, preferably in enterprise or mid-market segments
• Proven track record of closing complex deals with multiple stakeholders
• Experience selling into freight brokers, 3PLs, or supply chain organizations strongly preferred
• Familiarity with EDI, integrations, APIs, or logistics tech is a major plus
• Strong discovery, storytelling, and objection-handling skills
• Highly self-motivated with a hunter mentality
• Comfortable operating in a fast-paced, early-stage environment
• Must be willing to travel
• Must be located in the Greater Chicago, IL area.

Responsibilities

• Own and close enterprise-level deals (typically $25K–$100K+ ARR)
• Build and manage a pipeline of target accounts in the freight and logistics space
• Develop multi-threaded relationships with executives, IT, and operations leaders
• On-site regional visits to prospects
• Lead consultative discovery conversations around EDI, integrations, and workflow automation
• Deliver compelling product demonstrations and ROI-driven proposals
• Navigate complex buying processes and procurement cycles
• Partner with internal teams (product, partnerships, customer success) to craft tailored solutions
• Maintain accurate forecasting and pipeline visibility in CRM
• Represent Bitfreighter at industry events, conferences, and networking opportunities
• Limited travel during event season

Benefits

• Competitive base salary + uncapped commission (OTE: $150K–$250K+ depending on experience)
• 75% paid Health, dental, and vision benefits
• Unlimited PTO
• Summer Fridays
• 401k match
• Activity reimbursement

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed