Case Notes/Answers
Harry Rosen Digitizing Customer Relationships By Vania
Sakelaris, Nicole Haggerty
Discussion Questions:
1. Historically, what factors have given rise to Harry Rosen’s success in the menswear industry?
2. Describe the objectives and elements of the digital strategy that Ian Rosen developed. What were
some of the key considerations and implementation enablers?
3. What technology solutions did Ian Rosen consider? Describe the pros and cons of these options in
the context of the aims of his digital strategy.
4. Describe some of the strategic risks and opportunities that emerged for consideration with the onset
of the COVID-19 pandemic.
, W27515
Teaching Note
HARRY ROSEN: DIGITIZING CUSTOMER RELATIONSHIPS1
SYNOPSIS
Ian Rosen, the recently appointed Executive Vice President of Digital and Strategy at Harry Rosen Inc.
(Harry Rosen), a successful men’s retail chain founded by Ian’s grandfather in 1954, must decide on a
technology solution to support the advancement of his proposed digital strategy for Harry Rosen. The
decision-making challenges he is encountering in early 2020 are compounded by the onset of the global
pandemic and resulting impacts on the luxury menswear family retail business. Given the timing of the
onset of COVID-19, the challenges and opportunities related to the replacement and upgrading of the
company’s e-commerce platform have been heightened. Strategic investment and the seamless execution
of a new digital strategy are imperative components of the sustainability of the retailer’s success. Ian must
review and consider three different options, finalize his decision and proposal, and be prepared to launch
earlier than originally planned.
TEACHING OBJECTIVES
Working through this case will allow students to do the following:
• Understand the role that technology can play in the advancement of a strategy.
• Understand the role of business leaders in strategic decision-making related to the implementation of
technology projects.
• Assess the pros and cons of the technology solution options reviewed by the protagonist.
• Familiarize themselves with the leader conviction required to advance a transformation effort in a high-
risk macroeconomic environment and deal with the associated uncertainty.
• Build an understanding of consumable commerce.
1
All case facts and case research that are referenced in this teaching note are supported by the sources and information
contained in the associated case document (product no. W27514) unless otherwise specified.
This Teaching Note is authorized for use only by DR. CAMILLA JENSEN, University of Nottingham until Mar 2026. Copying or posting is an infringement of copyright.
or 617.783.7860.
Harry Rosen Digitizing Customer Relationships By Vania
Sakelaris, Nicole Haggerty
Discussion Questions:
1. Historically, what factors have given rise to Harry Rosen’s success in the menswear industry?
2. Describe the objectives and elements of the digital strategy that Ian Rosen developed. What were
some of the key considerations and implementation enablers?
3. What technology solutions did Ian Rosen consider? Describe the pros and cons of these options in
the context of the aims of his digital strategy.
4. Describe some of the strategic risks and opportunities that emerged for consideration with the onset
of the COVID-19 pandemic.
, W27515
Teaching Note
HARRY ROSEN: DIGITIZING CUSTOMER RELATIONSHIPS1
SYNOPSIS
Ian Rosen, the recently appointed Executive Vice President of Digital and Strategy at Harry Rosen Inc.
(Harry Rosen), a successful men’s retail chain founded by Ian’s grandfather in 1954, must decide on a
technology solution to support the advancement of his proposed digital strategy for Harry Rosen. The
decision-making challenges he is encountering in early 2020 are compounded by the onset of the global
pandemic and resulting impacts on the luxury menswear family retail business. Given the timing of the
onset of COVID-19, the challenges and opportunities related to the replacement and upgrading of the
company’s e-commerce platform have been heightened. Strategic investment and the seamless execution
of a new digital strategy are imperative components of the sustainability of the retailer’s success. Ian must
review and consider three different options, finalize his decision and proposal, and be prepared to launch
earlier than originally planned.
TEACHING OBJECTIVES
Working through this case will allow students to do the following:
• Understand the role that technology can play in the advancement of a strategy.
• Understand the role of business leaders in strategic decision-making related to the implementation of
technology projects.
• Assess the pros and cons of the technology solution options reviewed by the protagonist.
• Familiarize themselves with the leader conviction required to advance a transformation effort in a high-
risk macroeconomic environment and deal with the associated uncertainty.
• Build an understanding of consumable commerce.
1
All case facts and case research that are referenced in this teaching note are supported by the sources and information
contained in the associated case document (product no. W27514) unless otherwise specified.
This Teaching Note is authorized for use only by DR. CAMILLA JENSEN, University of Nottingham until Mar 2026. Copying or posting is an infringement of copyright.
or 617.783.7860.
