Remote Vice President Learning Development Jobs in Orlando, FL

Department: Transportation
Reports to: EVP, Transportation, Logistics and Client Growth
Location: Remote or Hybrid
FLSA Status: Exempt (Salary)
Position Summary
The Vice President of Transportation is responsible for leading the strategic direction, operational performance, network development, and financial results of OneRail’s transportation business. This executive leader will drive transportation excellence through the development and execution of scalable network strategies, customer-focused solutions, operational innovation, disciplined cost management, and strong Logistics Partner relationships.
The Vice President of Transportation will work closely with executive leadership, commercial teams, customers, technology, operations, and other functional stakeholders to optimize transportation services, maximize profitability, strengthen strategic partnerships, and support OneRail’s long-term growth objectives.
As a key member of the leadership team, this individual is accountable for building and maintaining a safe, compliant, efficient, scalable, and customer-centric transportation network while delivering sustainable growth and financial performance.
Key Responsibilities
Strategic Leadership & Business Growth

• Develop and execute a multi-year transportation strategy aligned with OneRail’s overall corporate, commercial, and growth objectives.
• Define and implement scalable transportation network strategies that support same-day, next-day, scheduled, and on-demand delivery capabilities.
• Identify new market opportunities, service offerings, network capabilities, and strategic partnerships that create competitive differentiation and enterprise value.
• Partner with Commercial, Customer Success, Operations, Product, and Technology teams to develop transportation solutions that address customer needs while achieving OneRail’s financial and operational objectives.
• Represent OneRail externally through industry forums, strategic partnerships, technology ecosystems, and professional networks to identify emerging trends, disruptive innovations, and opportunities that position OneRail as a transportation and logistics leader.

Transportation Network & Operational Leadership

• Provide executive oversight of transportation network performance, capacity, service quality, operational scalability, and overall network health.
• Develop and execute strategies to optimize transportation modes, Logistics Partner capacity, geographic coverage, and service capabilities.
• Establish performance standards and operating mechanisms that drive consistency, reliability, efficiency, and continuous improvement across the transportation network.
• Proactively identify and mitigate operational risks while leading business continuity and contingency planning across the network.
• Ensure transportation operations consistently meet customer service expectations, contractual commitments, and internal performance objectives.
• Drive continuous improvements in network utilization, service performance, cost efficiency, and operational resilience.

Logistics Partner Management & Procurement

• Lead the strategic management of OneRail’s Logistics Partner network, including capacity, performance, pricing, service quality, and business continuity.
• Develop and execute strategies to optimize total wallet share with Logistics Partners while appropriately managing concentration and business risk.
• Lead the negotiation and execution of master service agreements, pricing agreements, and other strategic commercial arrangements with Logistics Partners.
• Manage performance management frameworks, including scorecards, business reviews, and improvement plans, to ensure Logistics Partners consistently meet OneRail’s operational, financial, and customer requirements.
• Identify, evaluate, and onboard new Logistics Partners to expand network capabilities and support future growth.
• Drive procurement strategies that balance cost competitiveness, capacity, service quality, geographic coverage, and strategic value.

Customer Pricing & Commercial Support

• Lead the development, evaluation, and negotiation of transportation pricing strategies for OneRail customers.
• Partner with the Commercial organization to ensure customer pricing aligns with network economics, service requirements, market conditions, and profitability objectives.
• Support strategic customer discussions by providing executive-level expertise on transportation capabilities, network design, pricing, and operational solutions.
• Continuously evaluate customer and network profitability and implement strategies to improve margins and long-term financial performance.

Financial & P&L Leadership

• Maintain accountability for the financial performance of the transportation business, including revenue, gross margin, contribution, operating expenses, and other key financial metrics.
• Develop and manage departmental budgets, forecasts, and financial plans.
• Identify and execute cost-reduction, productivity, and margin-improvement initiatives.
• Establish financial and operational reporting that enables data-driven decision-making and clear visibility into business performance.
• Balance growth initiatives with disciplined financial management to support sustainable, profitable expansion.

Continuous Improvement & Performance Excellence

• Continuously benchmark OneRail’s transportation network, operating costs, service performance, technology, and capabilities against leading internal and external organizations.
• Translate industry best practices and emerging market trends into actionable strategies that create competitive advantage.
• Establish a culture of continuous improvement, accountability, and operational excellence.
• Utilize data and analytics to identify root causes, improve processes, and drive measurable improvements in customer experience, cost, and performance.

Technology, Innovation & AI Enablement

• Partner with Product and Technology teams to advance transportation technology, automation, analytics, and network visibility.
• Lead the strategic adoption and application of Artificial Intelligence, Decision Intelligence, predictive analytics, and digital technologies to improve transportation planning, network optimization, productivity, autonomous decision-making, customer experience, and operational resilience.
• Champion the use of advanced analytics and technology to improve real-time visibility, forecasting, capacity planning, pricing, and operational decision-making.
• Identify and prioritize technology investments that improve scalability, efficiency, and competitive differentiation.
• Promote innovation across the transportation organization and ensure OneRail remains at the forefront of emerging transportation and logistics capabilities.

Team Leadership & Organizational Development

• Build, lead, mentor, and develop a high-performing transportation organization.
• Establish clear goals, accountability, performance expectations, and development opportunities for team members.
• Foster a culture of collaboration, ownership, innovation, urgency, and continuous improvement.
• Develop future leaders and build organizational capabilities necessary to support OneRail’s continued growth.
• Partner effectively across the organization to ensure alignment between transportation, commercial, technology, finance, operations, and customer success teams.

Safety, Compliance & Risk Management

• Ensure transportation operations and Logistics Partner relationships are managed in accordance with applicable regulatory, safety, insurance, and compliance requirements.
• Establish appropriate governance and risk management processes across the transportation network.
• Proactively identify and mitigate operational, financial, customer, and partner-related risks.

Qualifications & Requirements
Education

• Bachelor’s degree in Supply Chain Management, Logistics, Business Administration, Operations, or a related field required.
• MBA or advanced degree preferred.

Experience

• 10–15+ years of progressive leadership experience in transportation, logistics, supply chain, distribution, or related industries.
• Demonstrated experience leading complex transportation networks and managing significant operational and financial responsibility.
• Proven experience in transportation procurement, carrier or Logistics Partner management, contract negotiation, and pricing strategy.
• Experience leading scalable growth initiatives within a technology-enabled, high-growth, or complex operating environment preferred.
• Experience with same-day, final-mile, expedited, and/or multi-modal transportation solutions is strongly preferred.

Core Competencies

• Strong strategic and commercial acumen with the ability to translate business objectives into actionable transportation strategies.
• Exceptional financial and P&L management capabilities.
• Deep understanding of transportation network design, procurement, pricing, operations, and performance management.
• Highly analytical and data-driven decision-maker with strong problem-solving capabilities.
• Proven ability to lead cross-functional initiatives and influence executive-level stakeholders.
• Strong executive communication, negotiation, and relationship management skills.
• Demonstrated ability to build and lead high-performing teams in fast-paced and evolving environments.
• Knowledge of transportation regulations, compliance requirements, safety standards, and risk management.
• Forward-thinking approach to technology, automation, artificial intelligence, and digital transformation.

Leadership Profile
The successful Vice President of Transportation will be a strategic, commercially minded, and operationally disciplined leader who can balance growth, customer experience, network performance, and profitability. This individual must be comfortable operating at both the executive and operational levels, setting long-term strategy while maintaining a strong understanding of the day-to-day dynamics that drive transportation performance.
This leader will play a critical role in shaping the future of OneRails transportation network and ensuring the organization has the capabilities, partnerships, technology, and talent necessary to scale efficiently and profitably.
 

About OneRail
OneRail is a leading omnichannel fulfillment solution pairing best-in-class software with logistics as a service to provide dependability and speed to help businesses meet their delivery promise. With a real-time connected network of 12 million drivers, OneRail matches the right vehicle for the right delivery so brands lower expenses and increase capacity to rapidly scale their businesses. This people-plus-platform approach features a 24/7 USA-based exceptions team who maintain a 98% on-time delivery rate. By optimizing fulfillment processes, reducing costs and improving order accuracy with store-shelf-to-doorstep visibility, OneRail is committed to empowering clients and improving the customer experience.

OneRail was named to the Deloitte Technology Fast 500™ two years in a row, was ranked 19th in the 2025 FreightTech 25, named for the fifth year in a row to the FreightTech 100, was honored as one of Inc. magazine’s Best Workplaces 2023, was listed on Forbes’ lists of America’s Best Startup Employers for the last three years, was named to the Inc. 5000 two years in a row and was selected as the Last Mile Company of the Year for the 2024 SupplyTech Breakthrough Awards. To learn more about OneRail, visit OneRail.com.

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