Sales Trainer

About Trucker Path

Trucker Path is North America's leading platform for truckers and fleets, trusted by more than 1 million commercial drivers. The platform combines truck-safe GPS navigation, real-time road intelligence (fuel prices, parking, weigh stations), a live load board, and AI-powered fleet tools to help drivers, fleets, shippers, and brokers move smarter and safer. As Trucker Path expands rapidly, we're building a world-class sales organization to fuel that growth.

Role Overview

The Sales Trainer equips new hires and existing team members with the product knowledge, sales skills, and process fluency needed to perform at a high level from day one. This is a hands-on, dual-function role — when not delivering training or upskilling sessions, the Sales Trainer actively contributes to the team's revenue efforts by handling outbound sales calls.

This role demands more than curriculum delivery. The ideal candidate has personally carried quota, closed deals, and understands the pressure of a live sales floor. They earn credibility with senior Account Executives through depth of knowledge, directness, and real-world relevance — not just presentation polish.

Key Responsibilities

Training & Development

• Design, deliver, and continuously improve the Product and Sales Training curriculum for all new hires

• Facilitate onboarding training programs (minimum one month) prior to new hire endorsement to Operations

• Conduct regular upskilling sessions for existing Account Executives covering product updates, objection handling, pitch refinement, and sales process improvements

• Assess trainee performance throughout the training period and provide structured feedback and coaching

• Track training completion, assessment scores, and readiness indicators; report outcomes to Sales leadership

• Collaborate with Sales Operations and Product teams to keep training materials current and aligned with business priorities

• Identify skill gaps across the sales team and proactively recommend and execute targeted training interventions

Outbound Sales (Non-Training Hours)

• Actively conduct outbound sales calls during periods when no training class or upskill session is scheduled

• Work assigned prospect lists and contribute to pipeline generation targets

• Maintain accurate and timely call logs, activity notes, and disposition data in the CRM

• Meet or exceed defined outbound activity metrics (calls, connects, qualified leads) during non-training periods

• Apply the same sales methodology taught in training, serving as a live model of best practices

Qualifications

Must Have

• 2-4 years of quota-carrying B2B sales experience; must have personally carried a number and been held accountable to it

• Prior experience as a Sales Rep, Account Executive, or BDR in a structured outbound environment — not solely in a training or enablement role

• Demonstrated track record of hitting or exceeding individual quota targets

• Deep, working knowledge of the full B2B sales life cycle: prospecting, cold outreach, discovery, qualification, objection handling, demo/presentation, negotiation, and close

• Ability to diagnose exactly where a deal is stalling or where a rep is breaking down — not just that performance is off, but why

• Fluency in sales metrics — connect rate, conversion rate, pipeline velocity, win rate — and how to use them to coach with precision

• Comfortable delivering blunt, direct feedback to high-tenure reps; able to say the hard thing clearly and without hedging

• Thinks on their feet: able to coach live calls, respond to in-the-moment objections, and adjust training delivery based on the room

• Excellent communication, presentation, and facilitation skills

• Comfortable switching between trainer and individual contributor modes

• Proficient in CRM platforms and sales tools

• High attention to detail in documentation and reporting

Nice to Have

• Experience in fleet, logistics, SaaS, or trucking

• Prior experience in sales training, coaching, or formal mentoring

• Familiarity with structured sales methodologies (SPIN, Challenger, MEDDIC, or similar) and the ability to adapt them to the team's context

What Success Looks Like

• New hires consistently meet ramp targets within 30-60 days post-training

• Training content is regularly updated, grounded in real deal scenarios, and well-received by participants at all experience levels

• Outbound activity KPIs are met during non-training periods without prompting

• Senior AEs voluntarily engage in coaching sessions because they find it valuable, not because it's required

• Call reviews and coaching sessions produce measurable behavior change, not just agreement in the room

• The Sales Trainer is viewed by the team as both a credible coach and a productive contributor