Sales Trainer

ROLE OVERVIEW

The Sales Trainer is responsible for equipping 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 must be able to 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 1 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

Required — Sales Background

• Minimum 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
• Experience in fleet, logistics, SaaS, or trucking is a strong advantage
• Required — Sales Knowledge & Expertise
• 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
• Familiarity with structured sales methodologies (SPIN, Challenger, MEDDIC, or similar) and the ability to adapt them to the team's context

Required — Coaching & Facilitation

• Prior experience in sales training, coaching, or formal mentoring is a strong advantage
• Comfortable delivering blunt, direct feedback to high-tenure reps — able to say the hard thing clearly and without hedging
• Earns credibility with senior AEs through real-world experience and sharp diagnosis, not authority or tenure
• 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
• General
• Comfortable switching between trainer and individual contributor modes
• Proficient in CRM platforms and sales tools
• High attention to detail in documentation and reporting