Loadsmart

Sales Training Specialist

Loadsmart

full-time

Posted on:

Location Type: Hybrid

Location: Chicago • United States

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Salary

💰 $70,000 - $90,000 per year

About the role

  • Drive consistent, high-quality execution of sales training programs as hiring scales
  • Facilitate onboarding and ongoing sales training for customer and carrier-facing brokerage teams
  • Create compelling, cross-functional content including playbooks, talk tracks, GTM briefs, competitive guidance, sales-ready materials, and customer-facing narratives.
  • Compile, organize, and centralize training content from across the organization into a cohesive, up-to-date enablement hub
  • Create short-form learning assets recorded coaching, video role-plays, microlearning modules, practice scenarios, assessments, and facilitator guides.
  • Ensure training programs run smoothly by owning scheduling, coordination, preparation, and follow-through across multiple stakeholders
  • Partner closely with Sales leadership to translate strategy, frameworks, and priorities into executable programs
  • Reinforce training concepts with front-line managers and sales teams through structured check-ins and reinforcement
  • Utilize LMS and enablement tools (e.g., Litmos) to scale delivery, track engagement, and drive adoption
  • Diagnose training needs using feedback, observation, and performance metrics to identify gaps and opportunities
  • Apply multiple training methodologies, including classroom facilitation, workshops, virtual learning, role-plays, self-paced modules, and on-the-job coaching
  • Explore and leverage new tools and technologies, including AI-enabled solutions, to improve training efficiency and effectiveness.

Requirements

  • 2+ years of experience in sales training, enablement or learning program development in a fast-paced, tech-driven environment
  • Experience facilitating, coordinating, or administering sales training programs
  • Proven ability to develop or enhance training content and materials
  • Strong presentation and facilitation skills across live, virtual, and blended learning environments
  • Exceptional written communication skills with the ability to simplify complex concepts
  • Highly organized with strong project management instincts and attention to detail
  • Demonstrated ability to build effective cross-functional relationships with Sales, HR, and brokerage leadership
  • Comfort managing training logistics involving multiple stakeholders and schedules
  • Hands-on experience with LMS platforms (Litmos experience a plus)
  • Strong technical aptitude and openness to leveraging new tools, including AI-enabled solutions
  • Knowledge of Salesforce and SalesLoft is a plus
  • Experience as a sales trainer in a tech/SaaS/logistics environment preferred, but not required
Benefits
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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
sales traininglearning program developmenttraining content developmentpresentation skillsfacilitation skillsproject managementtraining methodologiesperformance metricsAI-enabled solutionsSalesforce
Soft Skills
communication skillsorganizational skillsattention to detailrelationship buildingcoordination skillsadaptabilityproblem-solvingcollaborationcreativityleadership