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Tailored Clothing Leader

Reports To: Store Leader
Location: Bloor St., Toronto

Your Style, Your Career

Harry Rosen is a proudly Canadian born and raised retailer of fine quality menswear with store locations across the nation. We have been specializing in luxury menswear for over 70 years and have been officially recognized as one of Canada’s Best Managed Companies. We are committed to developing retail professionals who love retail and have the passion and ability to inspire exceptional service.

We are looking for a Tailored Clothing Leader to join our Store team. In this role you’ll be responsible for:

The Tailored Clothing Leader exists to drive performance and sales results in tailored clothing and made-to-measure by building capability, confidence, and consistency across the team.

Through hands-on coaching, training, and one-on-one partnership with advisors, this role focuses on teaching the skills and habits that lead to stronger conversion, higher productivity, and an elevated client experience.

By combining product mastery with leadership in service execution, the Leader ensures every advisor is equipped to confidently introduce and sell tailored clothing and MTM, delivering measurable growth for the store and reinforcing Harry Rosen’s position as the leader in this space.

As part of the store’s core leadership team, the Tailored Clothing Leader also contributes to the overall success of the business - supporting daily operations, carrying store keys, and modeling the selling culture by maintaining personal selling activity to keep their own skills sharp and connected to clients and the floor.

Key Responsibilities

1. Sales Leadership & Business Growth

• Drive the store’s tailored clothing and MTM sales performance, partnering with advisors to strengthen results through skill-building, coaching, and live selling support.

• Lead by example through personal selling and client engagement, ensuring firsthand understanding of client expectations, product evolution, and team challenges.

• Analyze sales trends, advisor skills, and missed opportunities to identify gaps and drive continuous improvement.

• Monitor and impact results in:

• MTM order accuracy

• Client penetration of tailored sales (percentage of clients purchasing tailored clothing or MTM)

• Develop and implement programs to support underperformers in becoming achievers through focused training, partnership, and accountability.

• Work closely with top performers to further expand their MTM and tailored business, leveraging them as role models and peer coaches to raise the overall bar of performance in the store.

• Collaborate with Central Office, vendor partners, and store leadership to maximize event performance, trunk show results, and seasonal MTM initiatives.

• Provide ongoing reporting and insights on performance, highlighting opportunities to improve productivity, client outcomes, and team execution.

2. Training, Coaching & Performance Development

• Deliver structured training sessions, one-on-one coaching, and skills evaluations focused on tailored clothing and MTM selling excellence.

• Build advisor confidence by reinforcing our Clothesmanship standards and the technical and service aspects of fitting, garment knowledge, and relationship-based selling.

• Partner with Sales Leaders, CELs, and DSAs to ensure advisors are trained on brand-specific product knowledge and craftsmanship details.

• Develop clear learning paths for both underperformers and high performers, ensuring growth at every level of the team.

• Create a culture of continuous learning where every advisor develops competence, confidence, and pride in the art of tailoring.

• Contribute to succession****readiness by developing internal talent for future leadership roles in tailored selling.

3. Client Experience & Quality Control

• Champion an exceptional client experience across all tailored clothing and MTM interactions.

• Monitor and report on:

• MTM Refusals – frequency and cause, using insights to coach advisors and reduce missed opportunities.

• Re-Alterations – percentage of garments requiring adjustments, identifying root causes and corrective actions.

• MTM Order Accuracy – tracking submission errors and adjustments required post-order.

• Partner with Tailor Shop leadership to ensure fittings, alterations, and delivery standards meet brand expectations and timelines.

• Lead service recovery and client follow-up for MTM or alteration-related issues.

4. Operational & Visual Standards

• Ensure the tailored clothing department and MTM areas consistently meet Harry Rosen’s standards for presentation, organization, and readiness.

• Maintain backstock areas to reflect a luxury, client-ready environment.

• Collaborate with Visual Presentation and vendor teams to ensure brand and category representation excellence.

• Support store opening, closing, and operational leadership duties as part of the core leadership team.

5. Partner Collaboration

• Build strong partnerships with vendor representatives, tailoring operations, and buying teams to align store execution with brand standards and business goals.

• Contribute insights and recommendations to improve MTM process efficiency, product performance, and client satisfaction.

• Serve as the in-store subject matter expert and liaison for all MTM updates, fitting protocols, and operational refinements.

• Act as the voice of the store, sharing best practices, performance results, and opportunities with national teams.

Compensation: $80-$90K + Performance Bonus (non-commissioned)

We thank you for your interest in this opportunity.

Harry Rosen Inc. is committed to ensuring that our environment is barrier-free to all persons, employees, and clients alike, as we believe in equal opportunity and fostering a diverse and inclusive environment. In the spirit of this philosophy, we are committed to providing reasonable accommodations to all applicants with accommodation needs in the interview and assessment process. If you need assistance during the selection process, please contact us at careers@harryrosen.com with details.