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 #J-18808-Ljbffr