- Employment
- Full-time
- Seniority
- Mid-Level
- Department
- Retail & Boutique Operations
- Industry
- Selective Retailing & Department Stores
- Posted
- Oct 25, 2026
About Harry Rosen
Founded in Toronto in 1954 by brothers Harry and Lou Rosen, Harry Rosen is a leading Canadian luxury menswear retailer, distinguished by its curated designer collections, tailoring expertise and personalized service. Its heritage combines entrepreneurial ambition with an enduring commitment to helping clients dress with confidence. As an employer, the company offers a setting where sartorial knowledge, relationship-building and commercial acumen intersect, with career paths spanning client advising, tailoring, merchandising and corporate functions. Professionals drawn to refined retail will find a business in which attentive service, product expertise and long-term client relationships are central to the brand’s identity.
Harry Rosen is hiring a Made-to-Measure Specialist for a full-time, permanent position at Rideau Centre in Ottawa. The specialist leads a designer brand or department, drives sales and repeat clientele, trains Advisors, coordinates trunk shows, and partners with buying and visual teams; compensation combines variable commission and team bonuses with a fixed base salary, with starting average annual income of $50,000–$70,000.
Role & Responsibilities
- Lead by example and focus on achieving sales goals while managing a designer brand or department.
- Deliver product knowledge training to Advisors and develop their taste level and understanding of the brand image.
- Drive personal sales through holistic in-store selling, building customer relationships and developing repeat clientele.
- Prepare for appointments and client meetings by planning merchandise presentations and identifying add-on sales opportunities.
- Communicate with buying and visual teams to ensure product inventory and the spirit of the brand are represented.
- Participate in and coordinate trunk shows.
- Inspire repeat exceptional customer experiences online and in-store through consistent training.
- Demonstrate an interest and ability to develop others.
- Build the team’s focus on achieving financial goals.
Qualifications
- At least 2 years of retail sales experience, preferably in a luxury environment, clothing, or store/department leadership.
- Experience in sportswear, footwear, accessories, outerwear, tailored clothing, or made-to-measure retail is preferred.
- Previous made-to-measure experience is an asset.
- Passion for inspiring repeat business through exceptional customer service experiences online and in-store.
- Willingness to participate in training initiatives and incorporate acquired skills into daily activities.
- Demonstrated interest in technology and using tech innovations to support retail customer service.
- Ability to work effectively as part of a team.
Skills
Experience
At least 2 years of retail sales experience, preferably in a luxury environment, clothing, or store/department leadership; previous made-to-measure experience is an asset.
Workplace
This position is based in Ottawa, Ontario, Canada.
Explore jobs in Ontario or in Canada.
Benefits
Eligibility to earn monthly and annual team bonuses; employee discounts and special purchase opportunities; comprehensive flexible benefits package; pension and Group RRSP programs; career coaching; opportunities for internal growth and promotion; modern, digitally advanced workplace; diverse and inclusive workplace.
Culture
Harry Rosen’s workplace culture reflects its heritage as a Canadian luxury menswear specialist, with an emphasis on sartorial expertise, personalised service and lasting client relationships. Its client-focused retail environment values attention to detail and collaborative service, with employees helping clients develop a wardrobe that expresses their individual style.
About Cerulean
Cerulean is the definitive career portal for the global luxury industry. We match exceptional professionals with exclusive opportunities at the world's most prestigious brands. From haute couture and fine watchmaking to prestige beauty, hospitality, and boutique retail, Cerulean centralises luxury employment to help you find the career for which you were destined.
Frequently Asked Questions
The luxury industry is characterised by a diverse and nuanced nomenclature. Esteemed houses frequently employ proprietary terminology, and even within a single organisation like Harry Rosen, titles may vary across global markets to reflect local conventions. To ensure absolute clarity, Cerulean assigns a standardised, industry-coherent canonical title to every listing. However, it is worth noting that this role is functionally synonymous with «Custom Clothing Specialist», «Bespoke Tailoring Specialist», «Made-to-Measure Advisor», «Custom Tailoring Advisor», and other variations. Our sophisticated search architecture anticipates these variations, ensuring that inquiries using related terms will seamlessly yield the exact roles you desire.