Director of Sales Training

Crucial Hire; Chicago, Winnetka (IL, IL); On-site; USD 190,000 - 220,000; Full time

Job summary

A leading enterprise organization is seeking a Director of Sales Training in Chicago, Illinois. This pivotal role involves strategic sales enablement and leading high-impact training programs. The ideal candidate will come with 7+ years of sales or account management success and proven experience in leading training that drives field behavior change. Compensation ranges from $190K to $220K base with additional incentives and requires up to 25% travel.

Qualifications

• 7+ years of real success in sales or account management, non-negotiable.
• Experience in building or leading sales training that changed field behavior.
• Advanced at presenting, facilitation, and influencing senior audiences.

Responsibilities

• Act as a trusted partner to senior sales and commercial leaders.
• Lead enterprise-scale sales training programs with clear ROI.
• Coach and develop a high-performing sales training team.

Skills

Sales success

Sales training experience

Influencing skills

Data validation

Presentation skills

Tools

PowerPoint

Excel

AI-enabled productivity tools

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