Director of Learning & Development

The Director of Learning & Development owns how Arrive develops and retains its early talent, starting with a new hire's first day in the classroom, through their role on the floor and beyond. This strategic leader will lead two connected programs, classroom training and floor training. Together, they form one coaching engine with a single goal of retention.

Responsibilities

Lead the Transformation: shadow classrooms, floor trainers, BD, Carrier and Client Success teams, and top performers in first 30 days, review current content, complete an opportunity analysis, and make necessary adjustments by 45-60 days; Own Classroom Training and Early Talent Development: direct the Classroom Manager and trainers, and build and implement programs for new hires; Drive Early Talent Engagement: cultivate classroom culture and community and connect early talent across offices, cohorts, and leadership levels; Lead Floor Training: manage floor trainers to ensure effective in-seat coaching post-classroom; Drive Retention Through Coaching & Collaboration: connect classroom, floor, and management coaching so new hires are supported at key moments; Spot Risk Early: analyze performance metrics and trainer feedback to identify struggling hires and intervene; Coach the Coaches: empower classroom trainers, floor trainers, and frontline managers with coaching skills, playbooks, and feedback rhythms; Build the Management Bench: oversee the two-year Management Development Rotational Program and deploy classroom trainers across Customer Operations, Customer Sales, Carrier Sales, and analytical roles; Evolve Continued Education: set continued education priorities and partner with a Content Strategist on agentic interfaces and personalized content; Partner on Management Development: collaborate with Management Development to feed the leadership pipeline; Measure What Matters: define and report impact on early talent retention to year two, ramp to productivity, program effectiveness, and growth into top performers and leaders; Other Project Needs: assist with additional strategic project needs as they arise

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 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 the integration of LMS platforms, digital tools, and personalized or AI-enabled learning technologies; Strong leadership presence with the ability to manage and influence teams across multiple geographical locations; Comfortable operating with variable compensation tied directly to strategic business outcomes and retention goals rather than output metrics; Thrives in a fast-paced, dynamic environment; able to manage shifting priorities while maintaining accountability and maximizing business impact; Willingness to travel across Arrive offices to facilitate engagement and program execution

Nice to have

Freight brokerage, logistics, or supply chain industry experience is highly preferred

Benefits

Medical, dental, vision, life, and disability coverage; Matching 401(k) program; Employee Resource Groups; Office-wide engagement activities, team events, and happy hours; Casual dress code; CTA and L train stops within walking distance and secure bike storage; LifeStart gym with Peloton bikes and personal training options; Free counseling sessions through Employee Assistance Program; Referral Program; Company paid holidays, paid vacation time, and wellness days; 100% paid parental leave; Relocation assistance