Sales Training Specialist

Loadsmart•Chicago, IL

3d•$70,000 - $90,000•Onsite

About The Position

Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)! We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less. With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork. As our organization continues to scale, we are investing in training and sales enablement as a core driver of seller performance, productivity, and consistency. We are hiring a Sales Training Specialist to serve as a key execution partner, working from our Chicago office. This role is designed for someone who thrives at the intersection of content development, facilitation, organization, and program execution. You will help ensure sales teams have the clarity, confidence, and capability to execute Loadsmartâs value proposition consistently - owning training delivery, materials, and coordination - while partnering closely with Sales leadership and strategic owners. This is not a âbuild it from scratchâ role. It is a high-impact opportunity to scale, strengthen, and operationalize a training foundation that already exists, while contributing thoughtful improvements within a clearly defined enablement philosophy.

Requirements

3+ years of experience in sales training, enablement or learning program development in a fast-paced, tech-driven environment - logistics/brokerage experience is preferred
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

Nice To Haves

Knowledge of Salesforce and SalesLoft is a plus.

Responsibilities

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.