Vice President of Strategic National Sales at Transportation Insight in Chicago, IL

Job description

The Vice President of Strategic National Sales is a senior, revenue-generating role responsible for driving new business growth across Enterprise, RFP-driven, and strategic LTL opportunities. This role owns a national pipeline while also serving as a force multiplier for office-based sales teams—supporting deal strategy, coaching, and execution on complex opportunities. The ideal candidate brings deep experience in third-party logistics, strong commercial acumen across LTL, TL, and multimodal solutions, and a proven ability to influence outcomes without direct people management authority. ESSENTIAL DUTIES AND RESPONSIBILITIES: Revenue Growth & Deal Ownership Own and grow a national pipeline of Opportunities including: Enterprise, Large-scale RFPs, Strategic LTL Account Management (LTL AM) opportunities, and Multimodal deals (LTL, TL, IMDL, WHSE, Final Mile, Etc.). Lead full sales cycle from discovery through close on assigned national accounts. Develop and execute deal strategies that align customer needs with brokerage capabilities, carrier networks, and pricing strategy. Partner closely with Pricing, Procurement, Operations, and Account Management to ensure competitive, executable solutions. Maintain accurate forecasting, opportunity tracking, and pipeline hygiene within CRM tools. Office-Level Sales Development & Support Act as a sales enablement partner to office-based sales teams: Support local sales reps on complex, high-value opportunities. Provide guidance on solution design, pricing strategy, and customer positioning. Participate in office-level sales strategy sessions, pipeline reviews, and opportunity planning. Coach and mentor sales reps on: Enterprise selling techniques RFP strategy and response development LTL-specific value articulation and pricing structures Help elevate office-level selling capabilities by sharing best practices, market insights, and competitive intelligence. RFP & Enterprise Strategy Lead or support end-to-end RFP management, including: Discovery and qualification Pricing strategy alignment Solution design and response development Final presentations and negotiations Ensure RFPs and enterprise pursuits are margin-accretive and operationally sound. Collaborate with leadership to prioritize high-value opportunities and allocate resources effectively. Cross-Functional Collaboration Partner with: Strategic Customer Executives and LTL Account Management to transition wins and support long-term growth Procurement & Carrier Management to align capacity, pricing, and service Operations & Implementation to ensure seamless onboarding and execution Serve as a voice of the customer, providing feedback that informs product, pricing, and process improvements. Performance Metrics New revenue and gross profit generated Pipeline size, quality, and conversion rate RFP win rate and enterprise deal velocity Office-level deal support impact (wins influenced, deal size uplift, cycle time reduction) Customer retention and expansion on national accounts JOB REQUIREMENTS: Bachelor's Degree in related field or equivalent. 7+ years of experience in 3PL / freight brokerage sales (Strongly preferred), with strong exposure to LTL and enterprise accounts. KNOWLEDGE, SKILLS , AND ABILITIES: Proven success managing and closing large, complex, multi-location deals. Deep understanding of RFP processes, pricing models, and brokerage economics. Demonstrated ability to influence, coach, and support sales reps without direct authority. Strong executive-level communication, presentation, and negotiation skills. Highly organized with strong CRM discipline and forecasting accuracy. Willingness to travel as needed to offices, customers, and industry events. **MAY PERFORM OTHER DUTIES AS ASSIGNED** Our Benefits: Competitive base salary (starting at $125k) + commission Paid time off Paid health days Company paid Holidays and Floating Holidays Paid parental leave Competitive Benefit Package, including Medical, Dental, Vision, and Pet ins