Director of Regional Sales
Location: Chicagoland Preferred
Travel: Approximately 75%
Compensation: $130,000–$150,000 Base + Incentive Compensation
Overview
A growing organization in the transportation and equipment leasing space is seeking a Director of Regional Sales to lead and develop a national team of Regional Sales Managers. This is a highly visible, hands-on leadership role focused on driving new business growth, increasing field activity, and improving overall sales performance across multiple territories.
This is not a sit-behind-the-desk management position. The ideal candidate will operate as a true player-coach — traveling alongside reps, supporting key customer opportunities, reinforcing accountability, and helping elevate the overall performance of the sales organization.
Responsibilities
- Lead, coach, and develop a team of Regional Sales Managers across the U.S.
- Travel regularly with reps in-market to support customer meetings, prospecting activity, and strategic sales efforts
- Drive pipeline generation, territory development, and new business activity
- Reinforce accountability around KPIs, customer engagement, and overall sales execution
- Assist with high-profile opportunities and complex customer sales cycles
- Partner closely with executive leadership on sales strategy, team development, and performance improvement initiatives
- Evaluate team performance and provide coaching, mentorship, and performance management as needed
- Maintain visibility into market trends, customer needs, and competitive activity within transportation and intermodal markets
Qualifications
- 7+ years of experience in transportation, logistics, intermodal, drayage, or equipment leasing sales
- Previous leadership experience managing or mentoring sales teams preferred
- Proven track record of generating net new business and building customer relationships
- Strong hunter mentality with a willingness to remain active in the field
- Experience managing pipeline activity, forecasting, and sales accountability metrics
- Comfortable operating in a fast-paced, performance-driven environment
- Strong communication, coaching, and relationship-building skills
- Ability and willingness to travel extensively (approximately 75%)
Preferred Backgrounds
- Intermodal transportation
- Drayage services
- Chassis or equipment leasing
- Asset-based transportation providers
- Fleet or transportation solutions sales
What Success Looks Like
- Increased field engagement and customer activity across the sales team
- Improved pipeline generation and quota attainment
- Stronger accountability and sales discipline within territories
- Growth in new business opportunities and long-term customer relationships
Why This Opportunity
This is an opportunity to join a growing organization at a pivotal stage and play a meaningful role in shaping the future of the sales organization. The role offers strong executive visibility, leadership influence, and the ability to directly impact business growth and team performance.