Commercial Enablement Learning and Development Manager

About the Role

Grade Level (for internal use): 10

automotive

Mastermind is experiencing significant growth within our Commercial Organization in 2025. We’re seeking a dedicated Commercial Enablement Manager to ensure our client-facing teams across multiple verticals are equipped for success with robust, high-touch onboarding and continuous development.

This role is pivotal in shaping the performance and consistency of our Commercial Organization by establishing scalable frameworks, materials, templates, and standards for training, evaluating, and supporting our teams.

This is a 100% remote position that requires regular domestic travel to conduct in-person training.

We are seeking a Commercial Enablement Manager to enhance the performance of our client-facing teams. This role blends strategy, content, and coaching to ensure our Commercial organization delivers consistent, high-quality customer experiences that fuel growth and retention.

Beyond product and process training, you will design and deliver programs that strengthen sales methodology, consultative skills, and customer engagement techniques. From teaching our teams how to structure conversations (e.g., Challenger-style) to building confidence in objection handling, storytelling, and negotiation, you will raise the bar for how we sell.

This role reports to the Director of Commercial Enablement and will have a significant influence on shaping how we enable, measure, and continuously improve performance across the Commercial org.

• Design and deliver ongoing enablement programs that close skill gaps, reinforce playbooks, and strengthen execution in the field.
• Embed a modern sales methodology (e.g., Challenger, MEDDICC, SPIN, or a hybrid approach) across our Commercial org, ensuring consistent language, frameworks, and execution.
• Deliver soft skills training that improves discovery, active listening, storytelling, negotiation, and executive presence.
• Partner with Product and Product Marketing to translate launches into training and readiness that are clear, actionable, and measurable.
• Build and maintain a library of scalable enablement assets (playbooks, frameworks, videos, LMS courses, templates).
• Facilitate live training sessions, workshops, and coaching sessions—both virtual and in-person—that are practical, engaging, and high-impact.
• Partner with Commercial leadership to identify performance gaps through data and feedback, then design targeted interventions to address these gaps.
• Track, measure, and report on program impact and enablement KPIs (adoption, proficiency, performance lift).
• Co-host large-scale events, including sales kickoffs, quarterly enablement sessions, and manager summits.

• 5+ years of experience in Sales Enablement, Sales Training, or a high-performing Commercial role (Sales, BDR, Customer Success).
• Experience implementing, coaching, and measuring a sales methodology (Challenger, MEDDICC, SPIN, or similar).
• Strong facilitation and coaching skills—confident leading workshops, role plays, and one-on-one development conversations.
• Proven ability to design clear, simple, and reusable training assets that drive adoption.
• Excellent organizational skills and the ability to prioritize in a fast-paced environment.
• Experience working cross-functionally with leaders across Sales, Product, and Marketing.
• Bonus points for:
  • Experience in SaaS or automotive technology.
  • Content creation or video production skills.
  • Familiarity with LMS or enablement platforms.

• Make an immediate impact by shaping how a rapidly growing Commercial org learns, sells, and succeeds.
• Be the driving force in embedding sales methodology and raising the bar for soft skills across the team.
• Work in a fast-paced, innovative environment where your ideas directly influence results.
• Be part of a culture that values collaboration, accountability, and growth.
• Flexibility:
  This role is remote-first, with domestic travel to team events and training sessions.

Equal Opportunity

Employer:

automotive

Mastermind is an equal opportunity employer and all qualified candidates will receive consideration for employment without regard to race, ethnicity, gender, sexual orientation, or any other protected status.