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Sales Training Specialist at Loadsmart

Loadsmart · Chicago, United States Of America · On-site

$70,000.00  -  $90,000.00

AWS

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Description

ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?

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 Loadsmart’s value proposition consistently - owning training delivery, materials, and coordination - while partnering closely with Sales leadership and strategic owners.
This is not a “build it from scratch” 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.

DEPARTMENT: Account Sales
LOCATION: Chicago - HQ

Job Type: Exempt

WHAT YOU GET TO DO:

  • 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.

    • REQUIRED QUALIFICATIONS:

  • 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.

    • Additional Information

    WORKING AT LOADSMART:

    • 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 

    At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

    It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.
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