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Arrive, an airport parking company, is seeking a Director of Learning & Development to lead a comprehensive transformation of the organization's talent development strategy. This is a hands-on leadership role that combines strategic vision with operational execution across classroom training, floor coaching, and management development.
In your first 30 days, you will shadow key teams—classrooms, floor trainers, business development, carrier and client success teams, and top performers—to understand current state and identify opportunities. By 45-60 days, you'll execute your strategic vision for onboarding, training, management development, and retention.
Key responsibilities include:
• Direct the Classroom Manager and trainers, establishing the classroom as the critical starting point for early talent development. Build programs that equip new hires with skills, confidence, and belonging.
• Manage Arrive's floor trainers to ensure effective in-seat coaching post-classroom, reinforcing foundational content and adapting to real-time performance data.
• Drive retention through integrated coaching across classroom, floor, and management levels, connecting support at moments when new hires are most likely to struggle or leave.
• Analyze performance metrics and qualitative feedback to identify struggling hires early and intervene 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.
• Set continued education priorities and partner with a Content Strategist to deliver personalized learning through modern platforms and AI-enabled interfaces.
• Collaborate with Management Development to ensure training initiatives feed into Arrive's leadership pipeline.
• Define and measure impact: early talent retention to year two, ramp time to productivity, program effectiveness, and identification of new hires who grow into top performers and leaders.
• Support additional strategic projects as needed.
The role requires travel across Arrive offices to facilitate engagement and program execution. You'll work in a fast-paced, dynamic environment with shifting priorities, and compensation will be tied directly to strategic business outcomes and retention goals rather than output metrics.
QUALIFICATIONS:
• 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 of designing, implementing, and scaling comprehensive classroom and on-the-job training programs for early-career talent in a high-volume sales or logistics environment.
• Demonstrated success in 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 integration of 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 operating with variable compensation tied directly to strategic business outcomes and retention goals.
• Freight brokerage, logistics, or supply chain industry experience is highly preferred.
• Thrives in fast-paced, dynamic environments; able to manage shifting priorities while maintaining accountability and maximizing business impact.
