Director of Learning and Development

arrivelogistics.com; Chicago (IL); On-site; USD 120,000 - 190,000; Full time

Job summary

Arrive Logistics is seeking a Director of Learning & Development to own onboarding and talent development. This strategic leader will unite classroom training and floor training into one coaching engine focused on retention.

You will direct the Classroom Manager and trainers, drive early talent engagement, and align coaching across offices to ensure new hires succeed and stay engaged.

Qualifications

• Experience leading onboarding and training programs.
• Proven ability to design and implement L&D initiatives.
• Strong coaching and instructional design capabilities.

Responsibilities

• Lead transformation of onboarding and training programs within 30–60 days.
• Direct Classroom Manager and trainers to build early talent development programs.
• Drive early talent engagement across offices and cohorts.
• Manage floor trainers to reinforce classroom content post-classroom.
• Coordinate coaching across classroom, floor, and management.
• Identify struggling hires and intervene with targeted coaching.

Skills

Leadership

Learning & Development

Onboarding

Coaching

Stakeholder management

Job description

Arrive Logistics is a leading transportation and technology company in North America with plans to grow significantly year over year. Our success is a testament to our remarkable team and what we’re building together. We’re committed to providing employees with a meaningful work experience and have established an award-winning culture that supports personal and career development in a fun, casual, and collaborative environment.

Who We Want

We build the people who build the business. 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. Classroom training is where early talent development and engagement begin and floor training is where new hires are coached in the seat. Together, they form one coaching engine with a single goal of retention.

What You'll Do

• Lead the Transformation: Shadow classrooms, floor trainers, BD, Carrier and Client Success teams, and top performers in your first 30 days. Review current content and complete an opportunity analysis of onboarding, training, management development and retention. Identify team needs and make necessary adjustments by 45-60 days to execute your strategic vision.
• Own Classroom Training and Early Talent Development: Direct the Classroom Manager and trainers, establishing the classroom as the critical starting point for early talent development. Build and implement programs that equip new hires with the skills, confidence, and sense of belonging needed to succeed and remain engaged.
• Drive Early Talent Engagement: Cultivate classroom culture and community to integrate new hires into the Arrive team. Leverage engagement initiatives and travel investments to connect early talent across various offices, cohorts, and leadership levels.
• Lead Floor Training: Manage Arrive’s floor trainers to ensure effective in-seat coaching post-classroom. Guarantee that floor training reinforces foundational content, adapts to real-time performance data, and proactively supports struggling hires.
• Drive Retention Through Coaching & Collaboration: Connect classroom, floor, and management coaching so new hires are supported at the moments they most often struggle or leave.
• Spot Risk Early: Analyze performance metrics and qualitative feedback from trainers to identify struggling hires. Intervene with targeted coaching and strategically redirect investments when necessary.