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Jobs at Bitfreighter (Now Hiring) — 1 open

Bitfreighter logoBitfreighter

Enterprise Sales - Chicago

Chicago, Illinois, United States · Remote OK

$150k–$250k/yr

Senior

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 Founded in 2020 by logistics leaders who saw a better way, we replaced outdated, transaction-based EDI wi…

Skills: Enterprise Sales, B2B SaaS Sales, Consultative Selling, Pipeline Management, Contract Negotiation

Bitfreighter logo

Enterprise Sales - Chicago

Bitfreighter

Chicago, Illinois, United States • Remote OK

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Senior

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  • $150k–$250k/yr
  • Full-time
  • Health Insurance, Dental Insurance, Vision Insurance, Unlimited PTO, Summer Fridays, 401k Match
  • Posted 3d ago
  • ~40 hrs/week
  • Remote in Chicago, Illinois, United States

Responsibilities

Drive new logo acquisition and strategic expansion within large freight brokerages, 3PLs, and logistics organizations. Manage the full sales cycle from prospecting and discovery calls to contract negotiations and closing enterprise-level deals.

Requirements

Requires 5+ years of B2B SaaS sales experience with a proven track record of closing complex enterprise deals. Experience in the freight, 3PL, or supply chain sector and familiarity with EDI and APIs is strongly preferred.

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 Founded in 2020 by logistics leaders who saw a better way, we replaced outdated, transaction-based EDI with unlimited messaging and seamless API integrations — automating quoting, tracking, and invoicing so our customers can focus on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

Related keywords

SaaSEnterprise SalesFreightLogistics3PLEDIAPIIntegration PlatformARRCRMSupply ChainWorkflow AutomationB2BConsultative SalesProcurementFreight Brokerage

About Bitfreighter

LinkedInVisit site

Our LiveQuote tool has the most sophisticated spotboard quoting rules engine in the logistics industry!

Industry
Truck Transportation
Company size
11-50 employees
Founded
2019
Headquarters
Nashville, TN
LinkedIn followers
3,588

Bitfreighter is transforming the freight industry by offering scalable, automated integration solutions for logistics professionals. Founded in 2020 by logistics executives frustrated with outdated transactionally priced systems, Bitfreighter simplifies freight operations by providing unlimited EDI messaging and seamless API shipper integrations. Our platform automates critical tasks through deep TMS integrations, like freight quoting, load building, updates/tracking, and invoicing, reducing human error while saving valuable time. We empower brokers to win more freight with our user-friendly tools, including LiveQuote, which delivers real-time truckload quotes to your shippers. Our commitment to superior customer support ensures you’re not just using a platform, but partnering with a team dedicated to helping you achieve operational excellence. Whether you’re a shipper, 3PL, or a Trucking company, Bitfreighter’s innovative solutions are designed to meet your needs as you grow. Join us in redefining freight connections. For more information, visit: www.bitfreighter.com

Offices: Nashville, TN 37209, US · Cleveland, OH, US · Austin , TX, US · Chattanooga, TN, US · Los Angeles , CA, US

View all jobs at Bitfreighter

About Bitfreighter

LinkedInVisit site

Our LiveQuote tool has the most sophisticated spotboard quoting rules engine in the logistics industry!

Industry
Truck Transportation
Company size
11-50 employees
Founded
2019
Headquarters
Nashville, TN
LinkedIn followers
3,588

Bitfreighter is transforming the freight industry by offering scalable, automated integration solutions for logistics professionals. Founded in 2020 by logistics executives frustrated with outdated transactionally priced systems, Bitfreighter simplifies freight operations by providing unlimited EDI messaging and seamless API shipper integrations. Our platform automates critical tasks through deep TMS integrations, like freight quoting, load building, updates/tracking, and invoicing, reducing human error while saving valuable time. We empower brokers to win more freight with our user-friendly tools, including LiveQuote, which delivers real-time truckload quotes to your shippers. Our commitment to superior customer support ensures you’re not just using a platform, but partnering with a team dedicated to helping you achieve operational excellence. Whether you’re a shipper, 3PL, or a Trucking company, Bitfreighter’s innovative solutions are designed to meet your needs as you grow. Join us in redefining freight connections. For more information, visit: www.bitfreighter.com

Offices: Nashville, TN 37209, US · Cleveland, OH, US · Austin , TX, US · Chattanooga, TN, US · Los Angeles , CA, US

View all jobs at Bitfreighter

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