- Location
- Mississauga Ontario Canada
- Employment
- Full-Time
- Seniority
- Mid-Level
- Department
- Retail & Boutique Operations
- Industry
- Fashion, Apparel & Leather Goods
- Posted
- Nov 10, 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 full-time, permanent Brand Specialist for Boss at Square One in Mississauga. The role leads sales performance and brand development, delivers product training, builds client relationships and repeat business, coordinates trunk shows, and supports team achievement of financial goals. Compensation combines variable commission, variable team bonuses and fixed base salary; starting average annual income is $50,000–$70,000.
Role & Responsibilities
- Lead by example and pursue 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 repeat clientele.
- Prepare for appointments and client meetings by planning merchandise presentations and identifying opportunities for add-on sales.
- 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 in developing others.
- Build a team focused 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 is preferred.
- Passion for inspiring repeat business through exceptional customer service experiences online and in-store.
- Willingness to participate in training initiatives and apply the skills acquired through those programs in daily activities.
- Demonstrated interest in technology and using technological innovations to support retail customer service.
- Ability to work effectively as part of a team.
Experience
At least 2 years of retail sales experience; experience in luxury, clothing, or store/department leadership preferred.
Workplace
The successful candidate will be located in Mississauga, Ontario, Canada, with easy access to Toronto.
Explore jobs in Ontario or in Canada.
Benefits
Eligibility for monthly and annual team bonuses; employee discounts and special purchase opportunities; a comprehensive flexible benefits package; pension and Group RRSP programs; a career coach; and a diverse and inclusive workplace with internal growth, promotion, and succession-planning opportunities.
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.