Summary
Jeremy Wacksman, the current CEO of Zillow, took a massive career risk in 2009 by leaving a stable job at Microsoft during a global financial crisis. While his friends and family were worried about the failing housing market, Wacksman saw an opportunity to build something new at a small, money-losing startup. His decision to lead Zillow’s move into mobile apps, inspired by the launch of the Apple App Store, helped turn the company into a multi-billion dollar success. Today, he credits his rise to the top to his willingness to say "yes" to new and unexpected challenges.
Main Impact
The transition from desktop websites to mobile applications changed the way people buy and sell homes forever. When Wacksman joined Zillow, the company was focused on its website, but the world was about to change because of the iPhone. By recognizing that mobile technology was the future, Wacksman helped Zillow dominate the real estate market at a time when many other companies were failing. This shift allowed users to search for homes and apartments directly from their phones, making the process much faster and more convenient. His leadership during this period proved that taking a chance on new technology during an economic downturn can lead to massive growth.
Key Details
What Happened
In early 2009, Jeremy Wacksman decided to quit his job as a marketing and product manager for Microsoft Xbox. This was a surprising move because the United States was in the middle of a severe housing crisis and a recession. Zillow was still a young company and was not yet making a profit. Despite the risks, Wacksman was driven by a passion for building products that stay in the minds of users. He joined Zillow as the Vice President of marketing and product, and within six months, he was tasked with leading the company’s move into the mobile app space.
Important Numbers and Facts
Zillow is now a major real estate firm with a market value of approximately $10.5 billion. Wacksman spent 15 years at the company before he was officially named CEO in August 2024. During his long career at the firm, he held several high-level positions, including Chief Marketing Officer, President, and Chief Operating Officer. His success was largely tied to the timing of the Apple App Store launch by Steve Jobs, which happened shortly after he started his new role. Because Wacksman had spent about 25% of his time at Microsoft working on mobile projects, he was the perfect person to lead Zillow’s mobile expansion.
Background and Context
The 2008 financial crisis was a very difficult time for the American economy. Many people were losing their jobs, and the housing market was in a state of collapse. During this time, most professionals were looking for safety and job security. Leaving a giant company like Microsoft for a real estate startup seemed like a bad idea to almost everyone Wacksman knew. However, Wacksman believed that the way people interacted with technology was about to change. He used his degree in marketing to focus on how to make a product essential to a user’s daily life, which eventually led him to see the potential in mobile apps.
Public or Industry Reaction
When Wacksman told his friends and family that he was leaving Microsoft, they were shocked. They questioned why he would want to work for a company that was losing money in a market that was currently failing. At the time, real estate was seen as one of the worst industries to enter. However, the tech industry soon realized that Wacksman’s move was a smart one. As mobile apps became the standard for business, other companies like Airbnb, eBay, and Etsy followed a similar path. Wacksman’s ability to ignore the doubts of others and focus on the future of technology is now seen as a key reason for his professional success.
What This Means Going Forward
Wacksman’s story shows that career growth often comes from being flexible and taking on tasks that are not in your original job description. He believes that his career was built on 15 years of saying "yes" to the next big thing, even if it was outside of his comfort zone. For Zillow, the future involves continuing to simplify the home-buying process through technology. Wacksman encourages other leaders to embrace new opportunities, even if they might fail. He argues that even a failed project provides lessons that make a person a better leader in the long run. The company continues to focus on its "housing super app" to keep its lead in the industry.
Final Take
Success often requires the courage to move in a different direction than everyone else. By leaving a safe job and embracing the mobile revolution early, Jeremy Wacksman didn't just help Zillow survive a crisis; he helped them lead an entire industry into the digital age.
Frequently Asked Questions
Why did Jeremy Wacksman leave Microsoft for Zillow?
He wanted to follow his passion for building products that stay in the user's mind. Even though the housing market was in a crisis, he saw an opportunity to grow with a startup that could change the industry.
How did Steve Jobs help Zillow become successful?
Steve Jobs launched the Apple App Store shortly after Wacksman joined Zillow. This allowed Wacksman to lead the company's move into mobile apps, which became the primary way people search for real estate.
What is Wacksman’s advice for career success?
He believes in saying "yes" to new responsibilities and challenges, even if they are not part of your official job. He credits his rise to CEO to 15 years of taking on new projects and learning from both success and failure.
