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Crucial Hire

Director of Sales Training

chicago, IL

Check who can apply and the requirements below before continuing.

About this opportunity

Crucial Hire lists this Director of Sales Training opportunity in chicago, Illinois. Review the employer’s description below for duties, qualifications and application requirements.

Job description

About the Company

Our client is a market-leading enterprise organization operating in a highly regulated, clinically nuanced environment where credibility is earned, not assumed.

Sales excellence here is not aspirational — it is mission-critical . Training that doesn’t show up in the field doesn’t survive.

About the Role

They are hiring a Director of Sales Training who can operate as a true partner to senior sales leadership.

This role is for someone who understands:

how reps actually sell (not how slides say they sell),

how managers really coach,

and how training either shows up in revenue… or gets ignored .

If you’ve never had to defend your training strategy to skeptical sales leaders, this will not be your role.

Responsibilities

Strategic Sales Enablement

Serve as a trusted, credible partner to senior sales and commercial leaders

Translate business priorities into focused, measurable training strategies

Act as the go-to expert on sales capability, readiness, and field execution

Training Design & Delivery

Lead enterprise-scale sales training programs with clear ROI

Own onboarding, field training, micro‑learning, and reinforcement strategies

Support major training moments (bootcamps, summits, national sales meetings)

Ensure training reflects business pace, customer reality, and clinical sensitivity

Team Leadership

Lead, coach, and develop a high‑performing sales training team

Set clear expectations, roles, and development paths

Foster a culture of accountability, candor, and continuous improvement

Measurement & Continuous Improvement

Measure training impact against sales metrics and rep activityUse data — not anecdotes — to refine programs

Maintain tight feedback loops with the field and sales leadership

Operational Excellence

Own training operations, budget, and execution discipline

Introduce tools and approaches that materially improve effectiveness

Build a team culture that solves problems instead of escalating them

Qualifications (Read Carefully)

You are likely a fit if you:

Have 7+ years of real success in sales or account management (non‑negotiable)

Have built or led sales training that changed field behavior

Are advanced at presenting, facilitation, and influencing senior audiences

Can challenge sales leaders respectfully — and hold your ground

Are comfortable operating on‑site in a fast‑moving enterprise environment

Use data to validate impact, not just tell a good story

Are fluent with modern tools (PowerPoint, Excel, AI‑enabled productivity tools)

Preferred Experience

Experience in clinically sensitive, regulated, or complex sales environments

Prior leadership of a sales training or enablement team

Compensation & Scope

$190K–$220K base + incentive eligibility

Up to 25% travel

Final Word

This is a career‑defining role , not a lateral move.

If this sounds like the kind of challenge you enjoy — or you know someone who fits this exactly — message

#J-18808-Ljbffr

Worksite address

chicago, IL, 60290, US

Who can apply

Review the original listing for work authorization, qualifications and employer requirements.

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