Head of Early Talent Development & Coaching

arrivelogistics.com; Chicago (IL); On-site; USD 170,000 - 210,000; Full time

Benefits offered by this job

Medical, dental, vision insurance

401(k) with matching

Relocation assistance

Wellness and Employee Resource Groups

Job summary

Arrive Logistics is a leading transportation and technology company seeking a Director of Learning & Development to own early talent development. You will lead classroom and floor training programs, shaping onboarding, engagement, and retention across multiple offices.

The role emphasizes building a coaching engine, leveraging data-driven insights, and partnering with leadership to grow a robust management pipeline. Chicago based with relocation support.

Qualifications

• 10+ years of progressive experience in learning & development, sales enablement, or sales leadership, including 5+ years leading multi-level teams.
• Proven track record designing, implementing, and scaling classroom and on-the-job training for early-career talent in high-volume sales or logistics.
• Demonstrated success creating training and coaching frameworks that improve retention and ramp time.
• Experience partnering with business development, account management, client success, or sales leadership.
• Exceptional coaching abilities; experience building coaching capacity among trainers and frontline managers.
• Highly analytical and data-driven; able to use retention, performance, and hiring metrics to inform decisions.
• Experience modernizing learning content delivery, including LMS integration and AI-enabled learning tools.

Responsibilities

• Shadow classrooms and floor trainers to assess onboarding and retention opportunities.
• Direct the Classroom Manager and trainers to establish the classroom as the starting point for early talent development.
• Build programs that give new hires skills, confidence, and belonging to stay engaged.
• Lead floor training and ensure coaching aligns with real-time performance data.
• Connect classroom, floor, and management coaching to support new hires through ramp and retention.
• Identify at-risk hires through metrics and intervene with targeted coaching.
• Develop coaching skills in trainers and frontline managers through playbooks and feedback rhythms.
• Oversee the Management Development Rotational Program across multiple functions to build future leaders.

Skills

Leadership

Coaching

Analytical thinking

Strategic thinking

Communication

Talent development

Tools

LMS platforms

AI-enabled learning tech

Job description

Arrive Logistics is a leading transportation and technology company seeking a Director of Learning & Development to own early talent development. You will lead classroom and floor training programs, shaping onboarding, engagement, and retention across multiple offices.

The role emphasizes building a coaching engine, leveraging data-driven insights, and partnering with leadership to grow a robust management pipeline. Chicago based with relocation support.