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.
RequirementsKey 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
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
- 100% remote
- Flexible work environment
