Enterprise SaaS Sales Exec — Freight & EDI

Bitfreighter; Chicago, Northern (IL, KY); Hybrid; USD 150,000 - 250,000; Full time

Benefits offered by this job

Unlimited PTO

100% remote

401k match

Health benefits

Summer Fridays

Job summary

Bitfreighter, a fast-growing freight tech company, is seeking an Enterprise Sales Executive for the Greater Chicago area to drive new logo acquisition and strategic expansion with large freight brokerages, 3PLs, and logistics firms.

You will own the full sales cycle from prospecting to close, managing a high‑quality pipeline, running discovery calls and demos, and leading contract negotiations with executives.

Qualifications

• 5+ years of B2B SaaS sales experience, preferably enterprise or mid-market
• Proven track record of closing complex deals with multiple stakeholders
• Experience selling into freight brokers, 3PLs, or supply chain organizations preferred
• Familiarity with EDI, integrations, APIs, or logistics tech is a plus
• Strong discovery, storytelling, and objection-handling skills
• Highly self-motivated with a hunter mentality
• Willingness to travel

Responsibilities

• Own and close enterprise-level deals (typically $25K–$100K+ ARR)
• Build and manage a pipeline of target accounts in freight and logistics space
• Develop multi-threaded relationships with executives, IT, and operations leaders
• Lead discovery conversations around EDI, integrations, and workflow automation
• Deliver product demos and ROI-driven proposals
• Navigate procurement cycles and contract negotiations
• Collaborate with product, partnerships, and customer success to tailor solutions
• Maintain forecasting and pipeline visibility in CRM
• Represent Bitfreighter at industry events and conferences

Skills

Enterprise SaaS sales

Multi-stakeholder selling

Discovery & storytelling

Hunter mentality

Travel willingness

Tools

EDI integrations

APIs

Job description

Bitfreighter, a fast-growing freight tech company, is seeking an Enterprise Sales Executive for the Greater Chicago area to drive new logo acquisition and strategic expansion with large freight brokerages, 3PLs, and logistics firms.

You will own the full sales cycle from prospecting to close, managing a high‑quality pipeline, running discovery calls and demos, and leading contract negotiations with executives.