The Broadway Angels investment group represents one of the few women-run angel groups in Silicon Valley. The group was founded by some of the most illustrious investors and operators with the mission to generate strong returns to members and inspire women in tech and investing. The case begins during the April 2014 investment meeting of the Broadway Angels. The members are evaluating an investment in Other Machine Co (OMC) and contemplating the structure of the angel group. Through the lens of these two key decisions, the case illustrates the factors that impact the angel fund's success and its ability to support entrepreneurs.

CEO, Ryan Smith and the rest of the founding team at Qualtrics grew the company to 350 employees and an estimated $50M in revenue through an inside-sales model. After ten years of bootstrapping however, the company took on $70M in funding from prominent venture capital funds. With this milestone, the team faced a new inflection point in the company's growth. To support the next phase of evolution, Smith brought in John D'Agostino as the new Head of Worldwide Sales. Smith and D'Agostino needed to increase revenue without negatively impacting the company's strong foundation. The Qualtrics leadership team faced several options for the future of their sales organization. It was up to Smith and D'Agostino to decide--how should they organize the sales team to face the challenges of Qualtrics' next phase of growth?

In March 2012 the founders of Qualtrics sat together in the Provo, Utah, office of advisor Duff Thompson. They stared down one of the toughest decisions in the ten-year history of the company. Thompson and Qualtrics' CEO Ryan Smith had spent the last few months fielding calls from venture capitalists and strategic partners who were interested in becoming a part of the Qualtrics story. The culmination of their effort was a $500 million buyout offer, several venture capital (VC) term sheets, and a line-up of prominent institutional partners. This case examines Qualtrics' growth through ten years of bootstrapping and challenges the reader to evaluate four potential liquidity options for the next phase in Qualtrics' evolution.