Enterprise Sales Executive — Freight Tech (Remote)

Bitfreighter; Chicago (IL); On-site; USD 150,000 - 250,000; Full time

Benefits offered by this job

Uncapped commission

Health, dental, and vision benefits

Unlimited PTO

Summer Fridays

401k match

Activity reimbursement

Remote work

Flexible work environment

Job summary

Bitfreighter is hiring an Enterprise Sales Executive to drive new logo acquisition and strategic expansion in the Greater Chicago area. You will own the full cycle from prospecting to close, targeting large freight brokerages, 3PLs, and logistics orgs with consultative, ROI-driven engagements.

You’ll manage multi-thread relationships, run discovery calls and demos, tailor proposals, negotiate contracts, and collaborate with marketing, product, and CS to ensure smooth handoffs and strong

Qualifications

• 5+ years of B2B SaaS sales experience with enterprise or mid-market focus.
• Proven track record closing complex deals with multiple stakeholders.
• Experience selling into freight brokers, 3PLs, or supply chain orgs preferred.
• Familiarity with EDI, integrations, APIs, or logistics tech a major plus.
• Strong discovery, storytelling, and objection-handling skills.
• Hungry, self-motivated hunter who travels as needed.

Responsibilities

• Own and close enterprise-level deals ranging from $25K to $100K+ ARR.
• Build and manage a pipeline of target accounts in freight and logistics.
• Develop multi-threaded relationships with executives, IT, and ops leaders.
• Deliver on-site regional visits to prospects and lead discovery calls.
• Provide compelling demos and ROI-driven proposals to stakeholders.
• Navigate procurement cycles and collaborate with product, partnerships, CS.
• Maintain accurate forecasting and CRM pipeline visibility.

Skills

B2B SaaS sales

Enterprise deals

Freight/logistics sales

EDI/APIs knowledge

Discovery & storytelling

Hunter mentality

Willing to travel

Tools

CRM

Job description

Bitfreighter is hiring an Enterprise Sales Executive to drive new logo acquisition and strategic expansion in the Greater Chicago area. You will own the full cycle from prospecting to close, targeting large freight brokerages, 3PLs, and logistics orgs with consultative, ROI-driven engagements.

You’ll manage multi-thread relationships, run discovery calls and demos, tailor proposals, negotiate contracts, and collaborate with marketing, product, and CS to ensure smooth handoffs and strong