WHO IS BITFREIGHTER

Bitfreighter started with one goal: make freight technology work for people, not against them. Founded in 2020 by logistics leaders who saw a better way, we replaced outdated, transaction-based EDI with unlimited messaging and seamless API integrations — automating quoting, tracking, and invoicing so our customers can focus on moving freight, not managing systems.

We care deeply about our people, our product, and the problems we set out to solve — and that hasn't changed as we've grown.

WHAT'S THE ROLE?

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.

Key Responsibilities

Own and close enterprise-level deals (typically $25K–$100K+ ARR)
Must be located in the Greater Chicago, IL area.
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

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What Success Looks Like

Consistently hitting or exceeding quota
Building a strong pipeline of qualified enterprise opportunities
Closing multi-stakeholder, high-value deals
Establishing Bitfreighter as a trusted partner within target accounts
Contributing feedback to refine messaging, product, and go-to-market strategy

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Qualifications

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

Bitfreighter is a fast-growing freight tech company transforming how brokers and logistics providers manage integrations and EDI. We provide a modern, managed integration platform that eliminates operational headaches, accelerates onboarding, and drives efficiency across the supply chain. By combining two products required to operate a logistics company into one platform, we help our customers cut costs and increase revenue.

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
100% remote
Flexible work environment

WHY BITFREIGHTER

Opportunity to make a significant impact in a growing company

2000% growth over 3 years
Massive opportunity in a legacy industry ready for modernization
Tight-knit, experienced team with deep industry connections
Clear product-market fit with strong customer demand
Ability to shape the sales motion and grow into leadership

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