Director, Learning & Enablement

OneRail

OneRail

Orlando, FL, USA
Posted on Mar 5, 2026

About OneRail

OneRail is a last mile delivery orchestration and fulfillment platform that connects shippers to an extensive carrier network, enabling fast, reliable, and scalable delivery solutions. As we continue to grow, we are investing in scalable learning systems, AI-driven enablement, structured talent development, and centralized knowledge management to support employees and customers efficiently and intelligently.

Position Summary
The Director of Learning & Enablement will design and lead OneRail's learning, documentation, and enablement strategy across internal teams and customer-facing initiatives. This leader will integrate AI-powered tools to increase efficiency, automate repetitive training and documentation functions, and reduce long-term headcount growth through smart enablement systems.
This leader will manage a team of approximately five and will be responsible for:
  • Internal training and continuous development programs
  • New employee onboarding
  • Customer training, adoption materials, and education programs
  • Employee career pathing and development
  • Centralized documentation, knowledge management, and process capture
  • Internal and external content production (SOPs, playbooks, guides, reference materials)
  • Process design, implementation, and workflow adoption across departments
  • AI enablement strategy to scale learning and documentation without linear headcount growth
This is a high-impact, build-and-scale leadership role focused on performance, adoption, operational leverage, knowledge capture, and workforce development.

Key Responsibilities

1. Enterprise Learning & Enablement Strategy

  • Develop and execute a company-wide learning, enablement, and knowledge management strategy aligned to OneRail's growth objectives.
  • Establish KPIs to measure training effectiveness, adoption rates, ramp time, productivity gains, documentation coverage, and cost-per-employee training.
  • Design systems that scale without requiring proportional increases in headcount.
  • Serve as the strategic owner for how OneRail captures, organizes, and distributes institutional knowledge.

2. AI-Driven Learning, Documentation & Automation

  • Identify, implement, and optimize AI tools to automate and enhance:
    • Training content creation and maintenance
    • Knowledge base and documentation management
    • Customer support documentation and self-service resources
    • Onboarding workflows
    • Internal certification tracking
    • SOP generation and version control
  • Develop AI-assisted training modules, simulations, and adaptive learning paths.
  • Partner with Product and Engineering to embed contextual learning and in-app guidance within the OneRail platform.
  • Reduce manual training delivery and documentation upkeep through automation and self-serve infrastructure.
  • Continuously evaluate emerging AI tools to improve productivity and reduce operational costs.

3. Documentation, Knowledge Management & Content Production

  • Build and maintain a centralized documentation ecosystem — including SOPs, process guides, reference materials, policy documents, and technical documentation.
  • Establish documentation standards, templates, and governance processes to ensure consistency, accuracy, and accessibility across all departments.
  • Lead the collection, organization, and curation of tribal knowledge into structured, searchable formats.
  • Produce internal materials (operational playbooks, department handbooks, change communications) and external materials (customer guides, implementation documentation, help center content).
  • Implement version control and review cycles to keep documentation current with product releases, policy changes, and process updates.
  • Partner with subject matter experts across the organization to capture and formalize undocumented processes and workflows.

4. Process Implementation & Workflow Adoption

  • Lead the design, documentation, and rollout of new processes and workflows across departments.
  • Develop change management and adoption strategies that ensure new processes are understood, followed, and sustained.
  • Create enablement materials — including quick-reference guides, video walkthroughs, and FAQ resources — to support workflow transitions.
  • Track adoption metrics and identify areas where additional training, documentation, or reinforcement is needed.
  • Collaborate cross-functionally with department leaders to identify process gaps, standardize best practices, and drive operational consistency.

5. Career Pathing, Certification & Talent Development

  • Standardize competency benchmarks and certification pathways across departments.
  • Design career development frameworks that give employees clear, measurable paths for growth.
  • Create advanced training tracks for high-performing team members.
  • Implement real-time training updates tied to product releases and process changes.

6. New Employee Onboarding

  • Design structured, role-specific 30-60-90 day onboarding programs.
  • Implement automated onboarding workflows and learning paths.
  • Reduce time-to-productivity across departments.
  • Create onboarding playbooks and digital resource hubs that integrate training, documentation, and process orientation.

7. Customer Training & Adoption Enablement

  • Lead development of scalable customer education programs, including:
    • Self-service LMS modules
    • Video libraries
    • Interactive walkthroughs
    • Implementation and onboarding documentation
  • Partner with Customer Success and Sales to improve product adoption and retention.
  • Develop training and documentation frameworks for enterprise implementations.

Qualifications

Required

  • 8+ years in Learning & Development, Enablement, Knowledge Management, or Talent Development leadership.
  • 3+ years managing teams.
  • Experience building scalable learning and documentation systems in high-growth SaaS or technology companies.
  • Demonstrated experience implementing AI tools for workflow automation, content production, or learning enhancement.
  • Strong instructional design expertise.
  • Experience with LMS platforms, knowledge management systems, and learning analytics tools.
  • Proven ability to design programs that improve productivity, reduce ramp time, and drive process adoption.
  • Experience leading documentation strategy, including SOPs, knowledge bases, and cross-functional content production.

Key Competencies

  • Strategic and systems-oriented thinker
  • AI-forward mindset
  • Operational scalability focus
  • Data-driven decision-making
  • Cross-functional leadership
  • Change management expertise
  • Strong executive communication skills
  • Documentation and knowledge architecture fluency

About OneRail

OneRail is a leading omnichannel fulfillment solution pairing best-in-class software with logistics as a service to provide dependability and speed to help businesses meet their delivery promise. With a real-time connected network of 12 million drivers, OneRail matches the right vehicle for the right delivery so brands lower expenses and increase capacity to rapidly scale their businesses. This people-plus-platform approach features a 24/7 USA-based exceptions team who maintain a 98% on-time delivery rate. By optimizing fulfillment processes, reducing costs and improving order accuracy with store-shelf-to-doorstep visibility, OneRail is committed to empowering clients and improving the customer experience.

OneRail was named to the Deloitte Technology Fast 500™ two years in a row, was ranked 19th in the 2025 FreightTech 25, named for the fifth year in a row to the FreightTech 100, was honored as one of Inc. magazine’s Best Workplaces 2023, was listed on Forbes’ lists of America’s Best Startup Employers for the last three years, was named to the Inc. 5000 two years in a row and was selected as the Last Mile Company of the Year for the 2024 SupplyTech Breakthrough Awards. To learn more about OneRail, visit OneRail.com.

About OneRail

OneRail is a leading omnichannel fulfillment solution pairing best-in-class software with logistics as a service to provide dependability and speed to help businesses meet their delivery promise. With a real-time connected network of 12 million drivers, OneRail matches the right vehicle for the right delivery so brands lower expenses and increase capacity to rapidly scale their businesses. This people-plus-platform approach features a 24/7 USA-based exceptions team who maintain a 98% on-time delivery rate. By optimizing fulfillment processes, reducing costs and improving order accuracy with store-shelf-to-doorstep visibility, OneRail is committed to empowering clients and improving the customer experience.

OneRail was named to the Deloitte Technology Fast 500™ two years in a row, was ranked 19th in the 2025 FreightTech 25, named for the fifth year in a row to the FreightTech 100, was honored as one of Inc. magazine’s Best Workplaces 2023, was listed on Forbes’ lists of America’s Best Startup Employers for the last three years, was named to the Inc. 5000 two years in a row and was selected as the Last Mile Company of the Year for the 2024 SupplyTech Breakthrough Awards. To learn more about OneRail, visit OneRail.com.