Rolex Training & Development Lead

Who We Are At Diamond Cellar, we believe in more than fine jewelry and timepieces — we believe in creating experiences that last a lifetime. For over 78 years, we have been a trusted name in luxury, known for our unmatched craftsmanship, and prestigious brand partners including Patek Philippe, Rolex, and David Yurman. We pride ourselves on delivering unparalleled customer service.

Diamond Cellar is dedicated to our employees – we foster a supportive and fun working environment which has led to a loyal team of employees who have been with us for decades.

What will you do as the Rolex Training & Development Lead at Diamond Cellar?

The Role x Training & Development Lead conducts Rolex learning, coaching, and training performance across all Diamond Cellar markets. This role ensures that associates and leaders representing Rolex deliver a consistent, knowledgeable, and elevated client experience aligned with Rolex and Diamond Cellar standards.

This role owns the Rolex training calendar, learning-app participation, e-learning development, manager reinforcement tools, monthly training meetings, field coaching, reporting, and continuous improvement. This is a hands-on, multi-market role that turns training data and store observations into clear actions that strengthen product confidence, clienteling, luxury hospitality, and sales readiness.

This highly visible role is responsible for building a consistent Rolex client experience through effective training, field coaching, manager support, and performance tracking. The ideal candidate combines luxury-watch knowledge, strong facilitation skills, and a passion for developing people in a high-performance luxury retail environment.

Training Strategy and Delivery 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.

Learning App and Compliance 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.

E-Learning and Training Tools 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.

Manager Support and Coaching 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,…