Director of Learning & Development

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

Who We Are

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.
• Coach the Coaches: Empower classroom trainers, floor trainers, and frontline managers with the necessary coaching skills, playbooks, and feedback rhythms to develop and retain their teams effectively.
• Build the Management Bench: Oversee the two-year Management Development Rotational Program, strategically deploying classroom trainers across Customer Operations, Customer Sales, Carrier Sales, and analytical roles to build a robust future management pipeline.
• Evolve Continued Education: Set continued education priorities using feedback from the Mentorship Directors, Advisory Board and Senior Leadership Team. Partner with a Content Strategist to meet employees where they are through agentic interfaces, delivering content based on individual performance and technology adoption.
• Partner on Management Development: Collaborate closely with Management Development to ensure training and coaching initiatives seamlessly feed into Arrive’s leadership pipeline.
• Measure What Matters: Define and report impact on the people you develop: early talent who reach year two in the seat, faster ramp to productivity, program effectiveness, and new hires who grow into top performers and leaders.
• Other Project Needs: Assist with additional strategic project needs as they arise, demonstrating flexibility and a proactive approach to supporting broader organizational goals.

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

The Perks of Working With Us

• Take advantage of excellent benefits, including medical, dental, vision, life, and disability coverage.
• Invest in your future with our matching 401(k) program.
• Build relationships and take part in learning opportunities through our Employee Resource Groups.
• Enjoy office wide engagement activities, team events, happy hours and more!
• Leave the suit and tie at home; our dress code is casual.
• Work in the heart of downtown Chicago, IL!
• There are CTA and L train stops walking distance from the office and you can store your bike safely inside of the building.
• Sweat it out at the LifeStart gym in our office building that includes brand new Peloton bikes, top-of-the-line equipment and personal training options.
• Maximize your wellness with free counseling sessions through our Employee Assistance Program
• Get paid to work with your friends through our Referral Program!
• Take time to manage your physical and mental health - we offer company paid holidays, paid vacation time and wellness days.
• Receive 100% paid parental leave when you become a new parent.
• Get relocation assistance! If you are not local to the area, we offer relocation packages.

$170,000 - $210,000 a year

The base salary range for this position is $170,000 - $210,000, plus bonus and benefits. The range displayed on each job posting reflects the pay range for the position across all locations. Within the range, individual pay is determined based on work location, job-related skills, experience, relevant education or training.

Your Arrive Experience

When we say “award-winning culture,” we mean it. We’ve been recognized as a top workplace by Inc. Fast Company, Fortune, and earned Top Workplaces and Great Place to Work, to name a few. We intend on topping many more of those lists in the years to come, but we’re not in it for the trophies. We’re committed to culture because it keeps us connected to each other and invested in our shared success while having a blast along the way. Our employee-founded resource groups create communities within Arrive’s walls, including Women in Logistics, Emerging Professionals, Prisms, Black Logistics Group, Salute and Unidos.