Interview with Julia DeWahl, Employee #10 at Opendoor

This article is part of a series revealing the stories of early employees from the most successful tech companies of the past few years. You’ll walk away having learned about what these individuals experienced, what they wish they knew, and the advice they’d give to others joining high-growth startups. Key takeaways are at the top and you can find the full interview below. 

This interview is with Julia DeWahl who joined Opendoor in 2014 as the 10th employee. She spent over 4 years at Opendoor working in various roles, most recently as Senior Director of Operations. Julia started her career at Bain, worked at SpaceX after Opendoor, and is currently an active angel investor. 

Note: If you’re looking for an all-in-one solution to manage your personal finances, Compound can help. We can help you diversify concentrated stock positions, optimize company equity, plan asset allocation, and more. Request access here and we’ll be in touch. 

Key Takeaways

• On learning what your customers want – “We used the term “liquidity” in some of our copy. People didn’t understand what we were talking about – they didn’t care about “liquidity”, instead, they wanted certainty that they would have an offer. They just wanted to sell this house to buy their dream house. Even though it meant the same thing to us, they meant very different things for the customer. We quickly learned what resonated with them.”
• A unique early Opendoor ritual – “One of the things that we did from the very beginning was share a customer story with the team every week. [...] it really focused the team on the “why”. Why are we working on this problem? Why are we working these long hours? What is our mission?”
• On using cross-team collaboration to build a better pricing model – “The field ops team realized that there was a key input missing from the pricing model: the floorplan layout. They were the ones to realize that we were buying some homes with outdated floor plans and missing out on some with newer, open floor plans. So the teams worked together to add that input and make the pricing model more accurate.”
• On using a geographical organization structure – “This ended up working well because there were differences between markets. In Dallas, for example, there are a lot more foundation issues than there are in the Phoenix just due to the clay soil and geological differences. It was important to let the GM incorporate that into the playbook for Dallas. “
• On diversifying a public stock position – “I’m a huge fan of Fred Wilson’s one-third selling model for how to take liquidity in a concentrated position. His philosophy is that when you have a liquidity event (for example, a company going public), you should break down your position into three equal buckets. Immediately sell one-third – capture your gains right away. With your next third, liquidate it and actively manage it almost like your own hedge fund. With the final third, keep it in the individual stock if you still believe in the business. It’s a long-term hold.”
• On pacing yourself if you angel invest – “Timelines also apply to deploying capital – you need to pace yourself. Some people begin angel investing, meet lots of founders and make investments really quickly. Then they realize that they invested all of the money they had allocated to angel investing. They might be seeing interesting deals now but have to miss out. So if you do angel invest, pace yourself and plan out how many investments you can make and over what time horizon."

How did you first hear about Opendoor? What made you decide to join?

I started my career working at Bain as a consultant which was a great introduction to a variety of types of companies and types of work. I did everything from surveys and qualitative work to financial modeling – it was like a business bootcamp right out of college. 

I knew I wanted to work at a startup and started reading TechCrunch. There was an article about Opendoor and I loved the idea. It was a new concept at the time to be able to simply – and with high certainty – sell your home. Real estate is also one of the biggest markets in the world and they had amazing founders and investors. I worked to get an intro to the company, got in touch with [co-founder & CEO) Eric Wu, and was really excited to get to work. 

What did you work on first? What was it like talking to early customers?

There wasn’t a job description that I was applying for at Opendoor. I came in as a generalist and was willing to work on whatever was the highest priority for the business. 

My first mandate was working on customer experience, and one of the first projects was putting up Facebook Ads in order to talk to customers. We would pitch Opendoor and learn what people thought. Did they understand what our product was? Were they interested? Why or why not? 

Refining our value proposition and how we talked about ourselves on our website was important for figuring out if we had product market fit. One thing we tried definitely didn’t land, which was the term “liquidity”. People didn’t understand what we were talking about – they didn’t care about “liquidity”, instead, they wanted certainty that they would have an offer. They just wanted to sell this house to buy their dream house. Even though it meant the same thing to us, they meant very different things for the customer. We quickly learned what resonated with them.

This first project was honestly so impactful to my development. It taught me that the most important thing really is to bring value to people. There were so many glimmers early on that Opendoor had found a solution to a real problem – people were very interested in a better way to sell their house. This process helped me learn that first-hand. 

Eventually I developed a playbook around what we would say, how we compared ourselves to working with a realtor and other parts of the customer experience process. I helped hire a team and set up processes & analytics in order for us to scale up the function. 

How did you find great people to hire?

There were two buckets of people we hired. 

First were the people who came from unlikely backgrounds – a very “Keith Rabois” type of hire. They wouldn’t necessarily come from top schools or have a traditional background, but they were hungry to work. In situations like this, we would just spread the word that we were a startup called Opendoor and if anyone was interested in joining to reach out. It was a good sign for those who showed the initiative to reach out. From there we looked for people who were willing to work hard and do anything that was needed to help the company. 

We would take bets on people and it often paid off well. It brought a diversity of skill sets to the table that we wouldn’t have otherwise found. 

The second archetype was people who had defined skillets where we knew what they would bring to the table. Later on, we would bring on specialists to work in specific roles. For that, searching through LinkedIn or using more formal recruiting processes usually worked for us. 

How would you describe the early culture? Were there any rituals that seemed ordinary but might’ve been unique to Opendoor?

One of the things that we did from the very beginning was share a customer story with the team every week. As part of the customer story, we would always include a photo of the customer. 

There were a few reasons why we did it. First, it really focused the team on the “why”. Why are we working on this problem? Why are we working these long hours? What is our mission? Second, it made sure we were building the right product. We were all getting to know the different types of customers that we had. We learned to be laser-focused on delivering value to our customers and honing our product to do that in the best way possible. 

Was there ever a time when you were worried about the future of Opendoor? How did you price the homes? 

Early on, there was a time when we thought we might actually run out of money in our line of credit that we were using for home purchases. Our growth was starting to take off but the financial markets hadn’t seen a model like Opendoor before. Plus, we didn’t have a track record as a company yet, so it wasn’t easy to get capital. It was the first time where I wondered if we were really going to make it. 

When we started getting into higher volume buying and selling home, we realized that a large portion of our homes didn’t perform well. We would lose money on them. We needed to tighten up our operations and our pricing in order to make it. 

Pricing was always a collaboration between the field operations team and the data science team. The data science team would pull information from publicly available sources (square footage, zip code, etc.) and combine it with on-the-ground data from our field ops team. I’m simplifying here, but a field operations manager might rate different factors they could see in person (like the quality of the interior) on a scale from 1-10 and send that data back to the data science team to add it to their pricing model. 

There was one interesting example of how these teams collaborated to solve pricing problems. The data science team would come up with one number to buy or sell a home, and the field ops team would come up with a different one. Somehow they weren’t adding up right. But the field ops team realized that there was a key input missing from the pricing model: the floorplan. They were the ones to realize that we needed to modify our price point depending on if it had a more desirable open floor plan, or an older or more awkward floor plan, which we hadn’t been doing. So the teams worked together to add that input and make the pricing model more accurate. 

How did Opendoor structure its organization? 

Just like any startup, there was a lot of change to our organizational structure and leadership team over time – it’s inevitable. One of the big questions we had to ask ourselves was, “Should we organize functionally or geographically?”

In the very early days, it made sense for us to organize functionally. We had a pricing operations team, a field operations team, a customer experience team, etc. We just needed to figure out the v1 playbook. 

As we expanded beyond our first market, it was important to move to a geographically-focused org structure so that we could finely tune the playbook for each market. We would have a GM in each city who was responsible for pricing, customer experience outcomes, looking through each home in the portfolio, and all of the other nitty-gritty details. 

This ended up working well because there were differences between markets. In Dallas, for example, there are a lot more foundation issues than there are in the Phoenix just due to the clay soil and geological differences. It was important to let the GM incorporate that into the playbook for Dallas. 

How did you think about the tradeoffs between salary and equity in your job offer? How did you first learn about exercising your options?

I was frankly much more naive about all of that than I am today. I honestly wish Compound existed when I started at Opendoor – I just didn’t give much thought to exercising options or how that worked. 

That said, I was aware that equity could mean a much larger upside in the future and that was something I actively wanted to optimize towards in my offer. And whether it was the initial offer or discussing raises / additional grants going forward, I was always very excited about what equity offers to employees. Fortunately, at the time I didn’t have large personal expenses I needed to cover so I decided to defer cash now for what could be more in the future. 

Opendoor was also quite proactive about at least having a conversation around refresher grants and raises once a year. The only advice I have for salary negotiations is to continue advocating for yourself and asking what you can be doing better. 

Opendoor went public last year. How did you think about diversifying from your concentrated stock position? 

I’m a huge fan of Fred Wilson’s one third selling model for how to take liquidity in a concentrated position. His philosophy is that when you have a liquidity event (for example, a company going public), you should break down your position into three equal buckets. Immediately sell one-third – capture your gains right away. With your next third, liquidate it and actively manage it almost like your own hedge fund. With the final third, keep it in the individual stock if you still believe in the business. It’s a strategy that allows for a balanced outcome whether the position goes up, down, or sideways, and takes some of the stress out of the decision-making around how to proceed in a liquidity event. 

How does angel investing fit into your portfolio? Any advice for people who want to get started? 

I started angel investing while I was at Opendoor and it’s absolutely the riskiest part of my personal portfolio – most companies that get venture funding go to zero. If you’re lucky, you might have one bet that counts for more than all of the others combined. It’s a major power law. 

The most underappreciated thing about angel investing is the long timelines and capital lockup. If you allocate X dollars to angel investing, you have to realize it’s going to be seven to ten years before you see that money come back (if at all). It’s important that you think on that longer time horizon. 

Timelines also apply to deploying capital – you need to pace yourself. Some people begin angel investing, meet lots of founders and make investments really quickly. Then they realize that they invested all of the money they had allocated to angel investing. They might be seeing interesting deals now but have to miss out. So if you do angel invest, pace yourself and plan out how many investments you can make and over what time horizon. 

Final note: If you’re looking for an all-in-one solution to manage your personal finances, Compound can help. We can help you diversify concentrated stock positions, optimize company equity, plan asset allocation, and more. Request access here and we’ll be in touch.