Enterprise Sales Director

Freightbull; Chicago (IL); Hybrid; USD 150,000 - 230,000; Full time

Job summary

Freightbull is seeking a high-impact Enterprise Sales leader to own the enterprise division end-to-end. You will build the playbook, pipeline, and team, while managing marquee accounts and driving long-cycle, RFP-driven wins.

This is a fast-paced, build-focused role reporting to the COO. You’ll collaborate closely with operations, pricing, and asset teams to architect solutions that differentiate Freightbull in a competitive market.

Qualifications

• 7+ years in logistics/freight/3PL with enterprise sales
• Proven track record closing six- to seven-figure RFP deals
• Experience building and leading sales teams
• Deep understanding of loads, pricing, and solution architecture
• Comfort with AI, data, and modern sales tooling
• Build-focused mindset, comfortable with ambiguity

Responsibilities

• Land enterprise customers including Fortune 1000 shippers
• Build and lead Enterprise Sales Executives team
• Stand up enterprise sales operating system (RFP response, account planning, QBR cadence, governance, win/loss reviews)
• Carry marquee accounts in Year 1
• Partner with operations, pricing, and asset teams to craft enterprise-grade solutions
• Represent Freightbull at HQs, during RFDefenses, and industry events

Skills

Enterprise sales leadership

People management

Operational fluency

Strategic account management

AI awareness

Tools

CRM software

RFP tooling

Job description

Freightbull Logistics is an asset-backed freight brokerage and carrier built around a simple idea: do what we say we'll do. Founded in 2012 by our owner — who started as the company’s first driver — we’ve grown to a $50M operation with 250+ tractors and trailers moving freight for major global manufacturers, CPG companies, and food and beverage shippers across the U.S., Canada, and Mexico. Our brokerage is our fastest-growing arm, and we’re now building the enterprise muscle to match. We’re not a traditional brokerage with a website, and we’re not a pure-tech digital broker pretending to understand freight. We’re building a next-generation logistics provider — combining decades of asset and operational depth with AI-assisted pricing, voice-enabled workflows, and intelligence tools built in-house. The future of this industry belongs to operators who can use both, and we’re building for it.

About the Role

This is a build, not a continuation. We don’t have an existing enterprise book to hand you. What we do have is a strong asset-backed foundation, real customer relationships, and a brokerage platform with momentum — and we need a leader who knows how to translate that into long-cycle, RFP-driven, strategic enterprise wins. You’ll report directly to the COO, work alongside a small senior leadership team, and own the enterprise division end-to-end: the playbook, the pipeline, the team, the customer outcomes. We move fast. Decisions get made the day they need to be made, not three meetings later. If that pace energizes you, you’ll fit here. If it makes you uncomfortable, this isn’t the seat for you. If you’re looking for a plug-and-play seat with a defined territory and inherited accounts, this isn’t it. If you want to roll up your sleeves and build something with real upside, read on.

Responsibilities

• Land net-new enterprise customers — Fortune 1000 shippers, complex multi-mode networks, strategic long-cycle relationships.
• Build and lead a team of Enterprise Sales Executives. Hire, onboard, develop, hold accountable.
• Stand up Freightbull's enterprise sales operating system — RFP response, account planning, QBR cadence, strategic account governance, win/loss reviews.
• Carry your own slate of marquee accounts in Year 1 while the team is being built. This is a lead-from-the-front role, not a manage-from-the-sidelines role.
• Partner with operations, pricing, and the asset team to architect enterprise-grade solutions our competitors can’t.
• Represent Freightbull externally — at customer HQs, on RFP defenses, at industry events.

What success looks like in Year 1

• A built team — Enterprise Sales Executives in seat, ramped, and producing.
• A closed slate of marquee strategic accounts driving meaningful new enterprise revenue.
• A documented enterprise sales playbook in active use across prospecting, qualification, RFP response, pricing, onboarding, and account growth.

Qualifications

• 7+ years of progressive sales experience in logistics, freight, or 3PL — including direct experience selling to enterprise/strategic accounts at scale.
• A track record of opening and closing complex, multi-stakeholder, RFP-driven deals with six- and seven-figure annual revenue.
• Direct people management experience — you’ve built and led sales teams, not just been a senior IC.
• Deep operational fluency. You understand how loads actually move, how pricing actually works, and how to architect solutions that deliver.
• Comfort with technology and curiosity about how AI, data, and modern tooling sharpen a sales motion. You don’t need to be an engineer or developer — but you can’t be allergic to working alongside tools smarter than the average broker stack.
• The temperament for a build — comfortable with ambiguity, decisive under pressure, willing to do the hands-on work alongside the strategic work.

Preferred Skills

• Experience standing up an enterprise division at a growing brokerage or 3PL.
• Existing relationships with national accounts in food and beverage, automotive, retail, or packaging.

Pay range and compensation package

We pay our producers like we mean it. Compensation at Freightbull is built to be among the strongest in the industry — base, bonus, and commission stacked so the people who deliver take home more than they would at the competition. Base salary, performance bonuses, and commissions tied to the production you and your team generate. Comprehensive health, dental, vision, and PTO benefits. Chicago (River North) - Hybrid schedule. Travel: approximately 10–15%, primarily for customer visits, RFP conversations, and strategic account events.

How to apply

Send your resume and a short note about why this role caught your attention to [e-mail]. We respond to every applicant.

Equal Opportunity Statement

Freightbull Logistics is an equal opportunity employer. We make hiring decisions based on the work you do and the way you do it — nothing else.