Sandy Kurtzig, Entrepreneur & CEO of ASK Group
Today, my guest is Sandy Kurtzig, who has been the founder, co-founder and investor in many successful software companies. She founded her first company, the ASK Group and grew the company into one of the ten largest software companies in the world and was the first woman CEO to take a technology company public.
She is the author of the best-selling autobiography, CEO: Building a $400 Million Company from the Ground Up and her latest company, Kenandy, is transforming the world of enterprise software on the cloud with a SaaS model. Sandy holds B.S. in mathematics from UCLA and an M.S. in aeronautical engineering from Stanford University.
In this candid conversation, Sandy shared the real stories behind her massive software startup, the immense value of starting a career in sales, and how a double-dare pulled her out of retirement.
1. The $2,000 Part-Time Job. Sandy revealed that she originally founded ASK Computers in her second bedroom simply because she wanted a flexible, part-time job that would allow her to start a family. Because she naively assumed babies would just sleep all day, she thought she could easily run a business in her spare time. Without taking any venture capital, she used a mere $2,000 to invent the first packaged manufacturing software for minicomputers, organically growing the massively successful company entirely through retained earnings.
2. The Equalizing Power of Sales. When advising young professionals—especially women—Sandy strongly recommends starting their careers in sales. While many fear discrimination in the workplace, she argues that sales is an incredibly equalizing field because performance is purely black and white; if you sell more on commission, you succeed. Additionally, the role provides an invaluable foundational education in understanding a company's technology, learning how to handle customers, and mastering financial presentations.
3. Weaponizing Low Expectations. Rather than letting the lack of female peers in the tech industry hold her back, Sandy actively used gender stereotypes to her absolute advantage. Because male clients rarely expected a woman to have a deep technical background, they were massively surprised and doubly impressed when she confidently answered their complex questions. Furthermore, being the only woman wearing a dress in a room full of male competitors ensured that potential customers always remembered exactly who she was.
4. A Cloud-Sized Double Dare. After happily retiring to Hawaii, Sandy's friend—Salesforce founder Mark Benioff—essentially "double-dared" her to return to the tech world. Recognizing a massive paradigm shift, Benioff convinced her that the industry desperately needed someone to rewrite enterprise manufacturing software specifically for the cloud, leading her to found her latest company, Kenandy (named after her two sons, Ken and Andy). Now stepping back from the CEO role, she is currently working on a new book tentatively titled Be in the Game, focusing on helping women successfully balance the demands of family life while building a business or climbing the corporate ladder.
