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Account Executive — SMB / Mid-Market
Hunt every day. Build a book that lasts.
Drive new customer acquisition and recurring lane business across our core customer book. Hunter-heavy, mostly self-sourced, building relationships that turn first deals into long-term lanes.
Chicago, hybrid, or fully remote
Travel ~5–10%
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 hunter seat. Lead flow at the SMB and mid-market tier isn't going to be handed to you — you'll build your book the way every great broker built theirs: list, call, qualify, quote, close, repeat. We've got the asset depth, pricing tools, and operational chops to back you up. What we need is the rep who can turn cold lists into recurring lanes. You'll report to our Manager of Customer Sales, work alongside a team of producing AEs, and run a mix of motions — high-velocity transactional quoting on spot freight where speed wins, and patient mid-cycle relationship building on lanes worth winning the long way. Both matter. 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 want a defined territory inherited from someone else, that's not what's on offer here. If you want to build a book you own — with tools and operational depth that make you sharper than your last seat — keep reading.
What you'll own
The work that's yours.
- Self-sourced prospecting into SMB and mid-market shippers across food and beverage, automotive, retail, packaging, and beyond.
- Running quotes, qualifying loads, closing first business, and turning first loads into recurring lanes.
- Building decision-maker relationships with logistics, traffic, and supply chain contacts at customer accounts.
- Working closely with carrier sales, operations, and pricing to deliver consistently — because the second load is what builds the book.
- Owning your weekly pipeline and activity targets — outbound calls, emails, qualified opportunities, quotes-to-close ratios.
- Contributing to Freightbull's customer-sales playbook as you find what works.
What success looks like in Year 1
The bar — twelve months in.
- A built book of recurring customers across multiple verticals.
- An established prospecting cadence and pipeline rhythm — something the next AE can model.
- Measurable contribution to team production — your book showing up in the team's monthly numbers.
- First customers coming back unprompted — the early signs of a book with stickiness.
What you bring
The experience we're hiring for.
- 5+ years of sales experience in logistics, freight, or 3PL — including direct experience selling to SMB and mid-market shippers.
- A track record of building a book from cold — outbound calling, prospecting from scratch, qualifying without inbound flow to lean on.
- Comfort with a mix of velocity and relationship — closing fast on spot freight when speed matters, patient enough to win the recurring lanes.
- 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 SMB and mid-market shippers in food and beverage, automotive, retail, or packaging.
- Experience with cold outbound at scale — call cadence, list-building, sequence work, CRM discipline.
- Multimodal exposure — truckload plus LTL, intermodal, drayage, or cross-border depth.
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.