In the aftermath of the 2008 financial crisis, Jeremy Wacksman, now CEO of Zillow, made a bold career move from Microsoft Xbox to the emerging real estate startup Zillow. Despite skepticism from friends and family, who questioned his choice to leave a stable position during a tumultuous time for the housing market, Wacksman recognized the potential for growth within the company.
Reflecting on his journey in a recent podcast, Wacksman noted that he joined Zillow as VP of marketing and product when the market was challenging. Shortly after his arrival, Apple launched the App Store, prompting a pivotal shift toward mobile platforms—something Wacksman capitalized on due to his prior experience at Microsoft. He embraced additional responsibilities, which significantly contributed to Zillow’s adaptation to mobile technology.
Wacksman’s strategy to say “yes” to new opportunities ultimately propelled his career within the company. Over the next 15 years, he held various leadership roles, including chief marketing officer, president, and chief operating officer, before becoming CEO in August 2024. He credits his willingness to engage with diverse projects, even in the face of uncertainty, as a foundational element of effective leadership.
As he reflects on his career, Wacksman emphasizes the importance of embracing challenges and learning from both successes and setbacks during one’s professional journey.
Why this story matters:
- Highlights the importance of adaptability and seizing opportunities in leadership roles.
Key takeaway:
- Embracing new challenges and responsibilities can lead to significant career advancement.
Opposing viewpoint:
- Critics may argue that moving to a struggling industry poses unnecessary risks, reflecting on Wacksman’s initial decision to join Zillow during a market downturn.
