Director of Regional Sales

Director of Regional Sales
Lombard, IL (On-site with National Travel)
Full-Time | Exempt
Base Salary:
$130,000 – $150,000 + 20% Target Bonus
Travel:
50–75% (national, field-based leadership role)

About the Role
Milestone Chassis is seeking a Director of Regional Sales to lead and scale a high-performing team of Regional Sales Managers across multiple territories. This role is responsible for driving new business growth, revenue performance, and disciplined sales execution across the region. You will lead a team of five (5) Regional Sales Managers, with a strong focus on coaching, accountability, and performance culture. This is a highly visible leadership role requiring industry expertise and the ability to influence results through people.

What You’ll Do
Partner with the VP of Sales to develop and execute regional sales strategies aligned with company growth goals
Lead, coach, and develop a team focused on new business generation and revenue growth
Establish and drive accountability around
KPIs, pipeline management, and activity metrics
Conduct performance reviews and implement development or corrective action plans
Develop and manage annual business plans and regional budgets
Optimize territories, account assignments, and lead distribution
Participate in key sales opportunities and maintain executive-level customer relationships
Recruit, hire, and develop top-performing sales talent
Analyze weekly and monthly sales performance and adjust strategy as needed
Approve pricing and customer credits within authority guidelines
What We’re Looking For
5+ years of progressive sales leadership experience
Background in equipment leasing, transportation, logistics, or related industries preferred
Proven success leading teams focused on new business development and revenue growth
Strong track record of meeting or exceeding sales targets
Experience building, coaching, and holding high-performing teams accountable
Excellent communication, leadership, and negotiation skills
Ability to thrive in a fast-paced, performance-driven environment
Willingness and ability to travel extensively (75–100%)
Proficiency in
CRM systems and Microsoft Office
Bachelor’s degree in business or related field (or equivalent experience)
Authorized to work in the United States
Compensation & Benefits
Competitive base salary:
$130,000 – $150,000
20% target bonus opportunity
Comprehensive benefits: medical, dental, vision, and retirement plans
Paid time off and additional company benefits
Why Join Milestone Chassis?

Lead a nationally distributed sales team with significant growth opportunity
High-impact role with direct visibility to executive leadership
Performance-driven culture with strong earning potential
Opportunity to shape sales strategy and drive business results