Rolex Training & Development Lead

Rolex Training & Development Lead

• Develop and execute an annual Rolex training calendar across all Diamond Cellar markets.
• Align learning priorities with Rolex brand standards, Diamond Cellar business goals, product launches, seasonal needs, and client-experience expectations.
• Serve as a subject-matter resource for Rolex heritage, product knowledge, storytelling, clienteling, luxury hospitality, and selling behaviors.
• Deliver monthly Rolex training meetings, workshops, onboarding sessions, product launches, role plays, and virtual or in-person development programs.
• Create structured learning paths for new hires, Rolex specialists, developing advisors, and leaders.

• Oversee Rolex training-app assignments, participation, completion, quiz results, certification, and recertification requirements.
• Monitor overdue training and partner with Store Directors and managers to ensure timely completion.
• Maintain accurate training records and provide regular reporting on participation, proficiency, and development needs.
• Create monthly scorecards by market, store, and associate to identify risks, gaps, and follow-up priorities.

• Create and maintain Rolex-specific e-learning courses, microlearning, knowledge checks, role plays, product resources, facilitator guides, and digital job aids.
• Adapt approved Rolex materials into practical Diamond Cellar learning experiences while maintaining brand standards.
• Develop content that strengthens product confidence, brand storytelling, appointment preparation, client discovery, follow-up, and long-term relationship building.
• Refresh learning content as products, business needs, and brand direction evolve.

• Create concise Manager Micro-Tool Kits for daily huddles, team meetings, one-on-ones, and coaching conversations.
• Provide leaders with ready-to-use huddle guides, observation checklists, coaching questions, role-play scenarios, and quick-reference tools.
• Conduct recurring market visits and observe Rolex client interactions, appointment execution, product presentation, and follow-up habits.
• Deliver real-time coaching and partner with leaders to build targeted development plans.
• Facilitate manager calibration sessions to ensure consistent expectations across all markets.

• Establish training measures that include completion, assessment results, certification, store observations, manager feedback, and relevant business indicators.
• Present a monthly Rolex Training Performance Report to leadership, including key metrics, coaching themes, market comparisons, accomplishments, and recommended actions.
• Conduct training needs assessments, learning audits, and store observations to identify improvement opportunities.
• Maintain an organized library of current learning content, manager tools, attendance records, reports, and assessments.

• Three or more years of experience in luxury retail training, luxury watch or jewelry sales leadership, learning and development, client experience, or multi-unit retail operations.
• Strong luxury-selling, clienteling, hospitality, and relationship-building skills.
• Rolex, luxury-watch, or premium jewelry category knowledge strongly preferred.
• Experience creating and facilitating instructor-led, virtual, and digital training.
•  Experience managing learning platforms, e-learning completion data, assessments, and training reporting.
• Strong coaching, observation, facilitation, presentation, communication, and project-management skills. 
• Ability to translate complex product and brand information into practical, client-facing learning.
• Comfort working independently, managing multiple priorities, and traveling regularly between markets.
• Proficiency with Microsoft 365, including PowerPoint, Excel, Teams, SharePoint, Forms, and digital-learning tools.
• Bachelor’s degree preferred; equivalent luxury retail and training experience considered.

• Medical, Dental, Vision coverage – Medical coverage starts day one
• Company paid Short Term Disability & Long Term Disability coverage 
• Employee Discount
• Company paid life insurance
• 401(k) program with a company discretionary match
• Paid Time Off
• Work-Life Balance – our stores are closed in the evenings and on Sunday
• Opportunity to work with the top brands in the luxury jewelry space
• Be a part of a passionate, loyal, dedicated team