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Crucial Hire

Director of Sales Training

Crucial Hire, Chicago

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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

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