Enterprise Sales - Chicago

Bitfreighter; Chicago (IL); On-site; USD 120,000 - 250,000; Full time

Benefits offered by this job

Uncapped commission

Competitive base salary

Health, dental, and vision

Unlimited PTO

401k matching

Remote work

Travel opportunities

Job summary

Bitfreighter is seeking an Enterprise Sales Executive in the Greater Chicago area to drive new logo acquisition and strategic expansion within large freight brokerages, 3PLs, and logistics organizations.

You will own the full sales cycle from prospecting to close, managing a high-quality pipeline, conducting discovery calls and product demos, and leading contract negotiations with senior decision-makers.

Qualifications

• 5+ years of B2B SaaS sales in enterprise or mid-market segments.
• Proven track record closing complex multi-stakeholder deals.
• Experience selling into freight, logistics, or supply chain is a plus.

Responsibilities

• Own and close enterprise-level deals ($25K–$100K+ ARR).
• Be located in the Greater Chicago, IL area and visit prospects on-site.
• Build and manage a pipeline of target accounts in freight/logistics.
• Develop relationships with executives, IT, and operations leaders.
• Lead discovery calls, demos, and ROI-driven proposals.
• Negotiate contracts with key decision-makers and stakeholders.
• Collaborate with product, partnerships, and customer success teams.
• Maintain accurate forecasting and pipeline visibility in CRM.
• Represent Bitfreighter at industry events and conferences.
• Travel as needed during events season.

Skills

Enterprise SaaS sales

Complex deals

Stakeholder management

EDI/APIs knowledge

Travel willingness

Job description

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 Founded in 2020 by logistics leaders who saw a better way, we replaced outdated, transaction-based EDI with unlimited messaging and seamless API integrations — automating quoting, tracking, and invoicing so our customers can focus on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

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

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