In 2009, Jeremy Wacksman transitioned from a marketing and product manager position at Microsoft Xbox to join Zillow, a struggling real estate startup during a challenging housing crisis. Despite the skepticism from friends regarding job security, Wacksman believed in Zillow's potential. Just six months after his arrival, Steve Jobs launched the Apple App Store, which marked a pivotal moment for the company, urging a shift from traditional desktop websites to mobile applications. Wacksman, who had mobile experience, took the initiative in adapting Zillow to this new platform. As the VP of marketing and product, Wacksman's willingness to expand his responsibilities beyond his primary role proved vital to Zillow's success. He contributed significantly to developing a mobile strategy, allowing users to engage with the real estate market through their phones. This strategic move not only saved Zillow but also positioned it as a leader in the market, further promoting rental applications on mobile devices. The mobile-first approach quickly became essential as the app landscape exploded, changing how consumers accessed real estate information. Over the next fifteen years, Wacksman's career flourished at Zillow as he ascended through various roles, eventually becoming the chief marketing officer and president. His ongoing commitment to embracing new opportunities was a consistent theme in his professional journey. By the time he was named CEO in August 2024, Wacksman had cultivated a reputation for his adaptability and leadership during transformative changes in the sector. In reflection, Wacksman acknowledges how his career journey was significantly shaped by a series of 'yes' moments. He learned valuable lessons about seizing opportunities, acknowledging that some projects may not yield success but contribute to personal and professional growth. This approach to leadership and willingness to embrace uncertainty has equipped him with the experience to steer Zillow effectively into the future, embracing technological advancements that shape the real estate landscape.