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Enterprise Sales Executive
Hunt for the next generation of logistics.
Be one of the first hunters into our newly launching enterprise division. Land net-new strategic accounts and build a book that grows with the division.
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 an early seat at a high-leverage moment. The enterprise division is being built right now — and Enterprise Sales Executives are the producers who turn the playbook into pipeline, and the pipeline into closed marquee accounts. You'll report directly to our Director of Enterprise Sales, partner with our operations, pricing, and asset teams to architect winning solutions, and own your own slate of strategic accounts end-to-end. 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've been an enterprise IC at a large brokerage and felt the friction of layers, approval cycles, and someone else owning your customer relationship — this is the seat where that friction goes away. If you want a defined territory inherited from a tenured AE, that's not what's on offer here.
What you'll own
The work that's yours.
- Net-new prospecting into Fortune 1000 shippers and complex multi-mode networks. Mostly self-sourced, supplemented by inbound RFPs and leadership-developed opportunities.
- Running the long-cycle, multi-stakeholder, RFP-driven selling motion from first conversation through close and onboarding.
- Building decision-maker relationships with logistics, procurement, and supply chain leadership at strategic accounts.
- Partnering with the Director of Enterprise Sales on the largest and most strategic opportunities — collaboration where two heads are better than one, not handoffs.
- Designing customer-specific solutions in coordination with operations, pricing, and the asset team.
- Contributing to Freightbull's enterprise playbook as you build your own book.
What success looks like in Year 1
The bar — twelve months in.
- A qualified pipeline of strategic accounts in motion across multiple verticals.
- A handful of marquee enterprise customers closed and onboarded — with more on deck.
- An established prospecting and account-planning rhythm that's repeatable.
- A documented set of learnings that sharpen the playbook for the reps who follow you.
What you bring
The experience we're hiring for.
- 5+ years of sales experience in logistics, freight, or 3PL, including direct experience selling to enterprise or strategic accounts.
- A track record of opening doors at Fortune 1000 shippers — door-knocking, list-building, multi-stakeholder navigation.
- Comfort running long sales cycles with multiple decision-makers and formal RFP processes.
- Operational fluency. You understand how loads actually move, how pricing actually works, and how to architect solutions that hold up.
- 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.
- Self-direction. You don't wait to be told what to do. You build your own week and own your number.
Bonus points
Nice to have, not required.
- Existing relationships with national accounts in food and beverage, automotive, retail, or packaging.
- Cross-border (U.S./Canada/Mexico) enterprise experience.
- Multimodal experience — truckload plus LTL, intermodal, drayage, or cross-border depth.
- Experience as an early sales hire at a growing brokerage or 3PL.
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.