Director of Sales / Sales Manager — Chicago (In-Office)

> **In-office, Chicago, IL — no remote.** 1 opening. Immediate hire. ## About the Role We're hiring a Director of Sales (Sales Manager) for a rapidly growing freight brokerage. Their sales force is built on individual brokers leveraging an industry-leading software stack, an established carrier network, and corporate financial backing to build and grow their own books. This is a Chicago-based leadership seat — you'll manage and grow the local sales team while running your own book. **Seat is in their Chicago office. No remote.** ## Responsibilities - Quickly transfer, establish, and grow your own book of business at the new shop - Provide professional client service and consultative support, implementing optimal solutions - Spearhead all sales-related initiatives — land business autonomously without hand-holding - Manage the Chicago office: recruit, hire, and train new sales reps - Direct management of sales and operations professionals — training, in-person mentorship, sales call coaching - Oversee Account Executive quotas and KPIs - Final say on new sales hires; partner with senior leadership on hiring decisions - Assist senior management with annual and quarterly P&L development for sales budgeting - Run frequent sales contests and team-building events - Develop and continually improve best practices for the sales team (templates, training materials, educational content) ## Required Qualifications - Must have a portable book of business (current/previous shipping clients you can transfer) - Hands-on experience in freight brokering and/or freight sales - 3-10 years of professional experience, including proven results in a management role - Track record of recruiting, hiring, and developing freight brokerage talent - P&L exposure and comfort with sales budgeting / forecasting - **In Chicago or willing to relocate** — this seat is in-office, no exceptions ## Compensation - Base salary: $85,000 - $100,000 - Commission: up to 35% - Bonus based on overall sales team performance - Opportunity for stock option grants based on performance ## What's Included - Comprehensive healthcare plan - Unlimited paid vacation - Dedicated Carrier Sales and Account Management teams to support your book - 24/7 after-hours operations staff (weekend and after-hours freight coverage) - Industry-leading technology — automated client updates, 24/7 live tracking, client logins - Small sales team with very low client concentration — diverse and lucrative pursuit opportunity ## Why This Role Entrepreneurial leadership seat with real upside. Build a Chicago office in-person, run your own book, lead a team face-to-face, and share in the equity story via stock option grants. The infrastructure (carrier network, tech, after-hours coverage, claims, ops) is already built — your job is to put points on the board and develop the reps under you.