Loadsmart · 3 hours ago
Sales Training Specialist
Chicago
Full-time
Onsite
Mid Level
$70K/yr - $90K/yr
3+ years expLoadsmart is a growth-stage technology company focused on reinventing the future of freight through innovative technology. The Sales Training Specialist will be responsible for driving the execution of sales training programs, facilitating onboarding, and creating training content to enhance sales team performance.
LogisticsSupply Chain ManagementTransportation
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
Qualification
Required
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
Knowledge of Salesforce and SalesLoft is a plus
Benefits
Competitive base salaries - we believe in rewarding top talent
Extremely competitive Equity package - become a shareholder in our company!
Loadie Time Off - PTO and sick days without a limit
Comprehensive Medical, Dental, and Vision insurance plans
401k Match
Company
Loadsmart
Loadsmart is a next-gen freight technology platform and 4PL that lower costs, increase efficiency, and digitize transportation for Shippers.
501-1000 employees
H1B Sponsorship
Loadsmart has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
2024 (2)
2022 (4)
2021 (9)
Funding
Current Stage
Late StageTotal Funding
$346.4MKey Investors
SOFTBANK Latin America Ventures
2022-09-01Undisclosed
2022-02-01Series D· $200M
2020-11-20Series C· $90M
Leadership Team
Felipe Capella
Co-founder, CEO
Ricardo Salgado
Founder and Executive Chairman
Recent News
Morningstar.com
2025-05-17
Company data provided by crunchbase