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Arrive, an airport parking logistics company, is seeking a Director of Learning & Development to lead a comprehensive transformation of their talent development strategy. This is a people-leadership role managing classroom trainers, floor trainers, and coaching initiatives across multiple office locations.
In your first 30-60 days, you will shadow key teams (classroom, floor trainers, business development, carrier, client success) to assess current training content and identify gaps in onboarding, management development, and retention. You'll then execute a strategic vision to transform early talent development.
Key responsibilities include:
• Direct the Classroom Manager and trainers, establishing classroom as the foundation for early talent development and building programs that equip new hires with skills, confidence, and belonging.
• Manage floor trainers to ensure effective in-seat coaching post-classroom, reinforcing foundational content and providing proactive support to struggling hires.
• Drive retention by connecting classroom, floor, and management coaching, identifying at-risk hires through performance metrics and qualitative feedback, and intervening with targeted coaching.
• Coach the coaches: empower trainers and frontline managers with coaching skills, playbooks, and feedback rhythms.
• Oversee a two-year Management Development Rotational Program, strategically deploying talent across Customer Operations, Customer Sales, Carrier Sales, and analytical roles to build a management pipeline.
• Evolve continued education by setting priorities based on feedback from mentorship directors and senior leadership, partnering with a Content Strategist to deliver personalized, AI-enabled learning content.
• Measure impact: define and report on retention of early talent to year two, ramp-to-productivity acceleration, program effectiveness, and identification of high performers who grow into leaders.
• Cultivate classroom culture and community through engagement initiatives and travel investments connecting early talent across offices and cohorts.
• Support additional strategic projects as needed, demonstrating flexibility in a dynamic environment.
Requirements:
• 10+ years of progressive experience in learning & development, sales enablement, or sales leadership, including 5+ years successfully leading and developing multi-level teams.
• Proven track record designing, implementing, and scaling comprehensive classroom and on-the-job training programs for early-career talent in high-volume sales or logistics environments.
• Demonstrated success creating training and coaching frameworks that measurably improve employee retention and accelerate ramp time.
• Background in business development, account management, client success, or sales leadership, or significant experience partnering closely with those teams.
• Exceptional coaching abilities with a history of building coaching capacity among trainers, floor trainers, and frontline managers.
• Highly analytical and data-driven; proficient in utilizing retention, performance, and hiring metrics to identify risks, evaluate training ROI, and inform strategic decisions.
• Experience modernizing learning content delivery, including LMS platforms, digital tools, and personalized or AI-enabled learning technologies.
• Strong leadership presence with ability to manage and influence teams across multiple geographical locations.
• Comfortable with variable compensation tied to strategic business outcomes and retention goals rather than output metrics.
• Freight brokerage, logistics, or supply chain industry experience highly preferred.
• Thrives in fast-paced, dynamic environments; able to manage shifting priorities while maintaining accountability.
• Willingness to travel across Arrive offices to facilitate engagement and program execution.
