Director of Learning & Development

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.