Sales Trainer

Description

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

Requirements

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