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Manager - Customer Sales
Build the team. Run the engine.
Lead our high-volume customer sales team. Coach the AEs producing today, hire the next wave, and stand up the operating system that turns activity into closed business.
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 hybrid seat — equal parts coach, builder, and operator. The customer sales team is the production engine of our brokerage: the AEs working SMB and mid-market shippers every day, turning prospecting activity into pipeline, pipeline into freight, and freight into recurring revenue. You'll inherit a team of producing reps, hire and onboard the next wave, and own the rhythms — pipeline reviews, deal coaching, performance accountability — that keep the engine running. You'll report directly to the COO and work alongside leadership to shape Freightbull's customer-sales playbook, hiring profile, and operating cadence. 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. This is a roll-up-your-sleeves role. You'll carry your own slate of customers alongside the team — leading from the front, not from a distance.
What you'll own
The work that's yours.
- Lead, coach, and develop a team of Account Executives selling to SMB and mid-market shippers across food and beverage, automotive, retail, packaging, and beyond.
- Hire the next wave of AEs — sourcing, interviewing, onboarding, ramping — in partnership with the COO and our recruiting team.
- Stand up the customer-sales operating system at Freightbull: 1:1 cadences, pipeline reviews, deal coaching, account planning, performance accountability rhythms.
- Carry your own slate of customers in parallel with the team — production credibility matters in this seat.
- Partner with operations, pricing, and carrier sales to keep the customer experience consistently sharp.
- Shape Freightbull's customer-sales playbook, hiring profile, and onboarding curriculum based on what's working and what isn't.
What success looks like in Year 1
The bar — twelve months in.
- A high-functioning team — AEs ramped, producing, and accountable to a clear set of expectations.
- Documented playbooks for prospecting, qualification, quoting, account growth, and rep onboarding — in active use.
- Weekly operating cadences (1:1s, pipeline reviews, team meetings) that are consistent and useful, not theatrical.
- A repeatable hiring and ramp process — so the next AE you hire ramps faster than the last one.
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 SMB and mid-market shippers.
- A track record of producing as an IC and leading other producers as a manager — you've coached reps to close, not just managed pipelines from a dashboard
- Direct people management experience. You've hired, ramped, coached, and held reps accountable.
- 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.
- 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 or scaling a customer-sales team at a growing brokerage or 3PL.
- Hands-on with sales hiring profiles, onboarding curriculums, and ramp programs.
- Cross-modal experience (truckload, LTL, intermodal, drayage) that informs how you coach reps to design customer solutions.
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.