From Gilt to Glamsquad: Alexandra Wilkis Wilson’s Journey Building Unicorns and Investing in Talent

Ken Pilot interviews Alexandra Wilkis Wilson for this episode of The Retail Pilot podcast.

Alexandra is an ENTREPRENEUR, INVESTOR & BOARD DIRECTOR.

She is best known as Co-Founder of ecommerce sensation, Gilt, which grew to $650M+ within 5 years of its launch and later sold to Hudson’s Bay Corporation. She was also Co-Founder of GLAMSQUAD, and Fitz, a closet organizing and styling company, which sold to Tradesy the peer-to-peer luxury recommerce company.

Today, Alexandra is Co-Founder and Managing Partner of growth equity fund, Clerisy, investing in consumer and techsumer companies. She has been an avid angel investor and advisor to over 80 consumer tech companies including Rent the Runway, The Mirror and Bubble. Alexandra is an active champion of female founders and the co-author of New York Times bestseller, “By Invitation Only: How We Built Gilt and Changed the Way Millions Shop”.

Summary

Alexandra discusses her entrepreneurial journey, starting with her time at Gilt and later founding Glamsquad. She shares the challenges and successes of both ventures and the lessons she learned along the way. She also talks about her involvement in other startups and her decision to join Clerisy, a growth equity fund. Alexandra discusses her career journey, the founding of Clerisy Partners, and their investment strategy. She highlights the importance of understanding consumer needs and solving problems in a unique way. Wilson emphasizes the hands-on approach of Clerisy Partners, where they actively partner with portfolio companies and provide support beyond capital. She also shares her leadership philosophy, the influence of mentor Mindy Grossman.

Takeaways

Alexandra Wilkis Wilson had an entrepreneurial spirit from a young age and pursued a career in investment banking before venturing into the world of retail and entrepreneurship.

Gilt, founded in 2007, grew rapidly and became a successful online luxury fashion retailer, attracting a large customer base with its timed sales and curated assortments.

Glam Squad, founded by Alexandra Wilkis Wilson, offered in-home beauty services and expanded to multiple markets, providing a hyper-local experience.

Alexandra Wilkis Wilson applied the lessons learned from Gilt to Glam Squad, including managing people, motivating teams, and giving and receiving feedback.

She later worked on other ventures, including Dressr, an app that used AI and machine learning to help users style outfits, and FITS, a service that organized consumers' closets and provided styling recommendations.

Alexandra Wilkis Wilson joined Clerisy, a growth equity fund, to continue her involvement in the tech and consumer-focused industry. Understanding consumer needs and solving problems in a unique way is key to successful investments.

Clerisy Partners takes a hands-on approach and actively partners with portfolio companies.

Delivering tough messages and providing constructive feedback is important for effective leadership.

Mindy Grossman has been a mentor and role model for Alexandra Wilkis Wilson.

Favorite streaming shows include El Tiempo Entre Costuras, Fauda, and Outlander.

Favorite vacation destinations are Key Biscayne and Brazil.

Taylor Swift is someone Alexandra Wilkis Wilson would love to meet.

Clerisy Partners aims to invest in the next unicorn among their portfolio companies.

Chapters

00:00

Introduction and Background

02:36

The Attraction to Gilt

05:34

The Early Vision and Success of Gilt

09:02

Gilt's Journey to Unicorn Status

12:07

Challenges and Exit of Gilt

15:29

Glam Squad: Inception and Expansion

18:44

Lessons Learned and Next Ventures

23:22

Dresser and FITS: Innovative Ventur...