Not long after landing at PagerDuty in 2016, Jennifer Tejada embarked on that harrowing rite of passage for CEOs of fortunate young startups: the pursuit of an IPO. Tejada raised a $90 million Series D round in late 2018, and saw PagerDuty go public on April 11, 2019. Her path to that point, she observes, was anything but linear. She tells the story of how a very “average” University of Michigan grad ended up becoming the CEO of a public SaaS company, and describes how gritty perseverance, some fortunate early leadership opportunities, and a passion for understanding and embracing different perspectives drove her career forward. She offers strategies that aspiring leaders can employ to challenge themselves and build tenacity while creating diverse, high-performing teams.