Chicago - Sr. Director of Sales

Responsibilities

• Develop and execute a comprehensive national sales strategy to drive revenue growth and expand market share across expedited freight and transportation service lines.
• Lead, mentor, and scale a high-performing sales team by setting clear performance expectations, providing ongoing coaching, and fostering a results-driven culture.
• Build and maintain strategic relationships with key enterprise accounts, freight brokers, and logistics partners to grow long-term revenue streams.
• Collaborate cross-functionally with operations, pricing, and customer service teams to ensure seamless onboarding and client satisfaction from contract through delivery.
• Analyze market trends, competitive landscape, and customer data to identify new business opportunities and refine go-to-market approaches.
• Establish and track KPIs, sales forecasts, and pipeline metrics, delivering regular reporting and strategic recommendations to executive leadership.
• Represent the company at industry events, trade shows, and customer meetings to elevate brand presence and cultivate new business relationships.

About the Company

This company is a leading provider of expedited freight and transportation solutions, specializing in time-critical shipments across North America. With a commitment to reliability and speed, it serves a diverse client base ranging from manufacturing and automotive to healthcare and retail industries. The organization operates a modern fleet and leverages advanced logistics technology to ensure on-time performance even under the most demanding conditions. Known for its customer-first culture and operational excellence, it has built a strong reputation as a trusted partner for businesses where every hour counts.

About Caliber

Caliber is a specialized talent solutions firm dedicated to connecting exceptional professionals with leading organizations across transportation, logistics, and supply chain industries. With deep market expertise and a consultative approach, Caliber goes beyond traditional recruiting to understand the unique culture and goals of each client partner. The team is committed to making placements that drive long-term success — for both the companies it serves and the candidates it champions