Director of Learning & Development

Arrive Logistics • Chicago, IL

15h • Onsite

About The Position

Arrive Logistics is seeking a strategic Director of Learning & Development to lead how the company develops and retains early-career talent. The role owns two connected programs—classroom training and floor training—which together support new hires from their first day of classroom instruction through in-seat coaching and continued development. The central goal is to improve retention, engagement, and performance.

The Director will assess current onboarding, training, management development, and retention efforts, then set and implement a strategic vision. They will lead classroom and floor trainers, strengthen coaching capabilities among trainers and frontline managers, and use performance data and feedback to identify and support employees at risk of struggling or leaving. The role also oversees a two-year Management Development Rotational Program and sets priorities for continued education, including personalized content delivered through digital and AI-enabled learning technologies.

The position measures success through outcomes such as early talent reaching their second year in the role, faster ramp to productivity, program effectiveness, and employees developing into top performers and leaders. It requires travel across Arrive offices. The position is based in downtown Chicago, Illinois, and offers a base salary of $170,000–$210,000, plus bonus and benefits.

Requirements

• At least 10 years of progressive experience in learning and development, sales enablement, or sales leadership.
• At least five years of experience successfully leading and developing multi-level teams.
• Demonstrated success designing, implementing, and scaling classroom and on-the-job training programs for early-career talent in a high-volume sales or logistics environment.
• A track record of creating training and coaching frameworks that measurably improve retention and accelerate ramp time.
• Background in business development, account management, client success, or sales leadership, or significant experience partnering closely with those teams.
• Strong coaching abilities and a history of building coaching capacity among trainers, floor trainers, and frontline managers.
• Analytical and data-driven approach, with proficiency using retention, performance, and hiring metrics to identify risks, evaluate training return on investment, and guide strategic decisions.
• Experience modernizing learning-content delivery, including LMS platforms, digital tools, and personalized or AI-enabled learning technologies.
• Strong leadership presence and ability to manage and influence teams across multiple locations.
• Comfort operating with variable compensation tied to strategic business outcomes and retention goals rather than output metrics.
• Ability to work in a fast-paced, dynamic environment, manage shifting priorities, maintain accountability, and maximize business impact.
• Willingness to travel across Arrive offices.

Nice To Haves

• Freight brokerage, logistics, or supply chain industry experience.

Responsibilities

• Shadow classrooms, floor trainers, business development, Carrier and Client Success teams, and top performers during the first 30 days; review existing content and assess onboarding, training, management development, and retention opportunities.
• Identify team needs and make adjustments within 45–60 days to execute a strategic vision.
• Direct the Classroom Manager and trainers, and build and implement classroom programs that equip new hires with the skills, confidence, and sense of belonging needed to succeed.
• Cultivate classroom culture and community, using engagement initiatives and travel to connect early talent across offices, cohorts, and leadership levels.
• Manage floor trainers and ensure in-seat coaching reinforces foundational content, responds to real-time performance data, and proactively supports struggling hires.
• Connect classroom, floor, and management coaching to support new hires at points when they are most likely to struggle or leave.
• Analyze performance metrics and trainer feedback to identify struggling hires, provide targeted coaching, and redirect investments when appropriate.
• Equip classroom trainers, floor trainers, and frontline managers with coaching skills, playbooks, and feedback rhythms.
• Oversee the two-year Management Development Rotational Program, deploying classroom trainers across Customer Operations, Customer Sales, Carrier Sales, and analytical roles to build a future management pipeline.
• Set continued education priorities based on feedback from Mentorship Directors, the Advisory Board, and Senior Leadership Team.
• Partner with a Content Strategist to deliver learning content through agentic interfaces based on individual performance and technology adoption.
• Collaborate with Management Development so training and coaching initiatives support Arrive’s leadership pipeline.
• Define and report impact measures, including early talent reaching year two in the seat, ramp-to-productivity time, program effectiveness, and new hires becoming top performers and leaders.
• Assist with additional strategic projects as they arise.
• Travel across Arrive offices to support engagement and program execution.

Benefits

• Medical, dental, vision, life, and disability coverage.
• 401(k) program with company matching.
• Employee Resource Groups and learning opportunities.
• Office-wide engagement activities, team events, and happy hours.
• Casual dress code.
• Access to an on-site LifeStart gym with Peloton bikes, fitness equipment, and personal training options.
• Free counseling sessions through the Employee Assistance Program.
• Referral Program.
• Company-paid holidays, paid vacation time, and wellness days.
• 100% paid parental leave.
• Relocation assistance and packages for candidates who are not local.
• Bonus in addition to base salary.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed