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Director - Enterprise Sales
Build something here.
Lead the launch of our enterprise division — strategy, accounts, team. Lead-from-the-front role, not manage-from-the-sidelines.
Chicago, hybrid, or fully remote
Travel ~10–15%
Full-time
About Freightbull
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 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.
What you'll own
The work that's yours.
- 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. Lead from the front, not from a distance.
- 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
The bar — twelve months in.
- 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.
What you bring
The experience we're hiring for.
- 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.
Bonus points
Nice to have, not required.
- 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.
- Cross-border (U.S./Canada/Mexico) enterprise account experience.
The Package
We pay producers like we mean it.
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 production
- Comprehensive health, dental, vision, and PTO benefits
- Chicago, hybrid, or fully remote (downtown Chicago office opening summer 2026; Tinley Park, IL HQ available for collaboration)
- Travel as noted per role
We respond to every applicant.
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.