automotiveMastermind Inc.
Commercial Enablement Learning and Development Manager
automotiveMastermind Inc., Granite Heights, Wisconsin, United States
Commercial Enablement Learning & Development Manager
AutomotiveMastermind Inc. is looking for a Commercial Enablement Learning & Development Manager to support our rapidly growing Commercial Organization in 2025. The role is 100% remote with regular domestic travel for in‑person training.
About The Role Grade Level:
10 (for internal use). The role focuses on building high‑touch onboarding, continuous development, and scalable training frameworks to elevate our client‑facing teams across multiple verticals.
Responsibilities
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 the Commercial organization, 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.
Partner with Commercial leadership to identify performance gaps via data and feedback, then design targeted interventions.
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.
Qualifications
5+ years experience in Sales Enablement, Sales Training, or a high‑performing Commercial role.
Experience implementing, coaching, and measuring a sales methodology such as 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, or familiarity with LMS or enablement platforms.
Benefits
Remote‑first role with domestic travel for team events and training.
Immediate impact on how a rapidly growing Commercial organization learns, sells, and succeeds.
Opportunity to shape sales methodology embedding and raise soft‑skill standards.
Fast‑paced, innovative environment that values collaboration, accountability, and growth.
Company Overview Founded in 2012, AutomotiveMastermind is a leading provider of predictive analytics and marketing automation solutions for the automotive industry. Through our proprietary Automated Sales and Marketing platform, Mastermind, the company empowers dealers to close more deals by predicting future buyers and consistently marketing to them. We are headquartered in New York City and thrive on high energy at high speed.
Equal Opportunity Employer AutomotiveMastermind is an equal‑opportunity employer and encourages applications from candidates of all backgrounds.
Location Remote, with domestic travel required for in‑person training and events. The role is based in the United States.
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About The Role Grade Level:
10 (for internal use). The role focuses on building high‑touch onboarding, continuous development, and scalable training frameworks to elevate our client‑facing teams across multiple verticals.
Responsibilities
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 the Commercial organization, 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.
Partner with Commercial leadership to identify performance gaps via data and feedback, then design targeted interventions.
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.
Qualifications
5+ years experience in Sales Enablement, Sales Training, or a high‑performing Commercial role.
Experience implementing, coaching, and measuring a sales methodology such as 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, or familiarity with LMS or enablement platforms.
Benefits
Remote‑first role with domestic travel for team events and training.
Immediate impact on how a rapidly growing Commercial organization learns, sells, and succeeds.
Opportunity to shape sales methodology embedding and raise soft‑skill standards.
Fast‑paced, innovative environment that values collaboration, accountability, and growth.
Company Overview Founded in 2012, AutomotiveMastermind is a leading provider of predictive analytics and marketing automation solutions for the automotive industry. Through our proprietary Automated Sales and Marketing platform, Mastermind, the company empowers dealers to close more deals by predicting future buyers and consistently marketing to them. We are headquartered in New York City and thrive on high energy at high speed.
Equal Opportunity Employer AutomotiveMastermind is an equal‑opportunity employer and encourages applications from candidates of all backgrounds.
Location Remote, with domestic travel required for in‑person training and events. The role is based in the United States.
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