Training Specialist

2 days ago


Chicago, IL, United States Transloop Full time

Title: Training Specialist

About the Role

The Training Instructor supports the learning and development needs of a fast-growing 3PL organization by designing and facilitating high-impact training across sales, carrier operations, and enterprise support teams. This role blends instructional design and delivery-analyzing business needs, creating targeted learning interventions, and onboarding new employees through both classroom and live-desk experiences.

What You'll Do

Learning Needs Analysis & Design

  • Conduct ongoing training needs analyses (TNA) in partnership with business leaders to identify performance gaps, skill trends, and process inefficiencies.
  • Translate business objectives into structured learning solutions that improve sales productivity, operational efficiency, and customer satisfaction.
  • Collaborate with SMEs to design engaging, scenario-based curricula aligned with company SOPs and logistics workflows.
Program Development & Facilitation
  • Develop and facilitate onboarding programs for new hires across departments, including Sales, Carrier Operations, Account Management, and Support.
  • Create and maintain training materials-presentations, facilitator guides, job aids, and eLearning modules-using adult learning and blended-learning principles.
  • Lead live workshops, system simulations, and interactive labs (Turvo, Highway, Parade, RingCentral, etc.) to accelerate learner adoption.
Implementation & Evaluation
  • Support smooth implementation of new systems and SOP rollouts by designing change-readiness training.
  • Evaluate learning effectiveness using Kirkpatrick Levels 1-3 and performance KPIs to drive continuous improvement.
  • Partner with leadership to ensure all onboarding graduates meet defined readiness benchmarks.
Hiring & Readiness
  • Partner with Talent Acquisition and Training to evaluate new-hire candidates through sales competency assessments and ride-along simulations.
  • Support onboarding cohorts by leading sales-focused learning tracks and ensuring role clarity before floor deployment.
Sales Coaching & Development
  • Conduct call reviews, side-by-side coaching, and performance clinics to reinforce best practices in prospecting, discovery, negotiation, and closing.
  • Develop frameworks and toolkits (e.g., MV(3)P sales discovery, objection handling guides, pitch frameworks) to improve rep quality and confidence.
  • Partner with frontline leaders to create individualized coaching plans and progression roadmaps for reps at various tenure levels.
Performance Enablement & SME Collaboration
  • Work cross-functionally with subject matter experts (Carrier, Operations, Compliance, and Technology) to embed enablement into ongoing workflow.
  • Leverage CRM and performance dashboards to analyze metrics (calls, talk time, conversion %, booked margin) and identify areas for enablement intervention.
  • Continuously refresh and upskill sales teams through workshops, contests, and quick-hit refreshers based on emerging market and product trends.
What You'll Need
  • 1+ years in Sales Facing Role
  • Strong knowledge of 3PL operations, including sales cycle, carrier management, and load lifecycle.
  • Excellent communication, facilitation, and stakeholder partnership skills.
  • Preferred: learning & development or training facilitation within a logistics, brokerage, or transportation environment.
  • Preferred: Proficiency in instructional design tools (PowerPoint, Articulate, Captivate, etc.) and LMS management.
Enjoy the good life: TransLoop wants you to love where you work so we offer
  • Competitive compensation
  • Uncapped pay & competitive salaries
  • Medical, dental, and vision coverage (50% paid by TransLoop)
  • Personal financial advisor
  • Wellness Days


About TransLoop

Imagine... working at a logistics company where all team members were supportive, had industry experience and the technology offerings did not look like an excel sheet... Imagine having free rein on all shippers in the country and not being tied down because your company saturated the entire market... Imagine carriers and shippers actually wanting to work with you... Imagine all drivers tracking in real-time, eliminating annoying check calls and issues like finding out a carrier isn't going to pick up a load because he did not answer his phone. Welcome to TransLoop, a much better logistics companyTransLoop is a modern digital freight network revolutionizing logistics for shippers and carriers of all sizes. The team pairs cutting-edge technology with white-glove service to deliver unparalleled transparency, industry-leading reliability, constant innovation, and real-time collaboration with every shipment.

Transloop is proud to be an Equal Employment Opportunity and Affirmative Action employer. We prohibit discrimination and or/harassment of any type, including but not limited to discrimination and or harassment based upon race, religion, religious creed, color, national origin, ancestry, citizenship, sex, sexual orientation, gender, gender identity, gender expression, age, pregnancy or relation medical conditions, childbirth, breastfeeding, parental status, veteran and/or military statue, disability (physical or mental) medical condition, genetic information or characteristics, political affiliation, domestic violence survivor status, marital status, or other characteristics prohibited by federal, state, or local law. Additionally, Transloop participates in the E-Verify program in all locations.

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this job. Duties, responsibilities and activities may change at any time with or without notice.
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