A Tale of a Fashion E-tailer: Scaling Dilemmas in Entrepreneurship

by: Julia Lee Cunningham

Publication Date: January 9, 2020
Length: 16 pages
Product ID#: 9-416-726

Core Disciplines: Entrepreneurship & Innovation, Leadership/Organizational Behavior

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Teaching Note

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This case provides a cautionary tale of the one-size-fits-all approach to organizational culture. Despite the success of Zappos.com and Southwest Airlines, not all companies’ culture achieves its intended outcomes for employers and employees. Through the eyes of fictional protagonist Roxie Steele, founder of StyleForYou.com and StreetFashion.com, students learn about issues that entrepreneurs face when they scale a business from startup to full-fledged enterprise. Although Steele launched a new fashion e-commerce site in 2019, StreetFashion.com, the case is largely based on Steele’s past experience as StyleForYou’s CEO from 2000 to 2015. Students gain insights into the entrepreneurial challenges StyleForYou.com faced within the competitive and fast-paced fashion industry.

Students apply a framework (i.e., leadership congruence model) to analyze the strengths and weaknesses of StyleForYou’s management practices, with a focus on organizational culture and structure. Students also develop solutions for Steele regarding how to establish StreetFashion.com as a sustainable enterprise in the future.

Teaching Objectives

After reading and discussing the material, students should:

  • Apply the leadership congruence model to analyze the situation.
  • Create arguments for or against StyleForYou’s culture and management practices (or lack thereof).
  • Identify managerial and strategic challenges associated with scaling up a startup business in the fast-changing, e-commerce retail business.
  • Articulate leadership strategies for effectively managing creative yet inexperienced employees.