We had the opportunity to sit down with Jacob Chai, to learn more about his world as Chief of Staff at the leading multi-family property management company, Common. Having joined the team as one of the first hires leading business development 5+ years ago, Jacob helped the organization navigate multiple waves of growth and market expansion before transitioning to his CoS role in mid-2020.
While Jacob's background is rooted in BD, he's applied a swiss-army style approach to his professional development to excel in his position - being a master of staying organized, a superb listener, and always keeping the company's mission in focus. More impressively, Jacob takes these skills one step further by continuously learning about his industry through his own entrepreneurial pursuits.
Read the full interview with Jacob —
You were one of the first employees at Common, what led to your CoS role?
I joined when we were around 15 people and we had just opened our first property in Crown Heights, Brooklyn. That was in February of 2016, so it’s been amazing to be a part of an organization and watch it grow for the last five and a half years. There definitely was not a Chief of Staff role at that time. I think people were wearing a lot of different hats and there was different overlap, but we were not at the point where we needed anything like a COS. I was living in New York city at the time and I joined to launch Common on the West coast. I took a business development role based in LA and moved from New York. I worked on developing relationships and structuring deals with our real estate partners. So building the supply side of the business.
I stayed in a business development role for about four and a half years. In that time the role was expanded from working on the West coast to covering all markets outside of the United States. I'm originally from Canada, so when we were getting a lot of international inbound and seeing some good opportunities outside of the US, it made sense for me to start to cover and tackle those. So I was focused on expanding our business in Canada and in Europe and signed our first deals in those markets.
In June/July of 2020, I was supposed to move to London, England to launch Common’s business in Europe when COVID shifted those plans, I started considering what other career paths within Common were available and interesting. It turned out that the existing Chief of Staff was transitioning to a new role.
The chief of staff role seemed to be a perfect fit to give me more breadth and visibility into how big strategic decisions were getting made. It also allowed me to be more internal facing. This was a great role to get maximum exposure to the top folks at Common and also get to support people throughout the entire organization. Working really closely with Brad, our CEO and Simon, our CIO, has been really incredible as part of that experience.
What most excites you about the Chief of Staff role?
There's a lot of variety, so I get to deal with new things everyday. I typically don't know how long I'm going to be working on those things, so it requires a lot of flexibility. I'm enjoying working on projects from 1-6 weeks that cross a really wide span of different initiatives.
What are you working on right now?
Some of my shorter term projects are figuring out how Common could source utilities from renewable energy sources. I'm very passionate about that and it’s been something on my mind for quite some time, but I wasn't really ever in the right kind of role to put something like that in place. As a CoS I am able to dive into that head first.
Other projects I’m working on:
- Developing a coordinated effort in unlocking ancillary revenues. This type of initiative naturally crosses a whole bunch of different teams.
- Managing our largest institutional real estate account. I kept that with me since transitioning from the real estate team and the business development side.
Projects like ancillary revenues and renewable energy are going to be shorter term, but are exciting things that I'm enjoying working on.
What’s something that you’re sneaky good at or that people wouldn’t expect about you?
Coming into the chief of staff role, I would say that organization was a challenge. I would not have claimed to be a very organized person. I had a few months heads up that I was going to be transitioning into the CoS role. And I knew this was something I had to improve.
I read the book, Getting Things Done (GTD) by David Allen. And then I went and hired a GTD coach and actively worked on transitioning my entire work style and backend of how I keep track of everything that I'm doing. What does it mean for me to sit down, to do any work? What does my workflow look like? I invested personally in that with both time and finances and it has paid huge dividends.
Now I do feel like I'm in control of my life, my world, and my landscape. And it couldn't have come at a better time because in a Chief of Staff role, there are too many important things. You can't drop the ball. There's too many people relying on you. And that applies to so many senior roles and it really applies to life in general. If you want to have a big fulfilling life, you have to be dependable. Organization is the framework for dependability.
Now I would say I am sneaky good at being really organized. That feels amazing.
What’s a framework that you or your founder use that you find indispensable?
After reading some of the articles written by other Chiefs of Staff, I often think am I an extension of my CEO or do I enhance their work directly? The answer for me is really both.
I work in different capacities with Brad, where in some cases I find myself playing a very direct supporting role. Where I will take on some more administrative things so that he doesn’t have to, like working with the Exec Team to ensure they’ve set company level OKR’. Making sure All Hands meetings are ready and programming is available is another good example. The same is true for our project managing out board slides or monthly board updates.
In other cases I work directly on key strategic projects and keep Brad updated on the progress. An example of that would be in ensuring we’re making progress on launching new Ancillary Revenue lines.
I can work directly with our Chief Investment Officer and other senior leaders in a way that allows our CEO to take a step back and be selectively involved at only the most important moments that we need him to be.
What’s your professional goal in the next ~10 years?
I've been involved with Common from the beginning. I'm excited to see how the story unfolds and to help see Common through the next few chapters of growth. I don't know what those are going to look like, but I know that our aspirations are around going public at some point and would love to participate in the chief of staff capacity in the IPO. The potential of that experience is very exciting.
Beyond that, I feel like I'm continuing to develop a toolkit and a way of being in the professional world and in the business world that I am excited to apply to other initiatives and endeavors that are my own entrepreneurial ideas. I've started businesses in the past, and I also have a real estate development company that I've been slowly building in Newburgh, New York. We've done six projects in the last 18 months. I’m happy to continue to see where that goes and over the next ~10 years my goal is to continue building new, amazing businesses that solve big problems and have local impact too.
I’ve been playing across the spectrum of impact between and renovating a few buildings in Newburgh, New York, and also trying to build the largest property management company in the world. I find a lot of joy and fulfillment in operating at both sides of the spectrum — super local and super global.
I’m lucky to have both aspects of this industry at my fingertips right now. I do think that real estate will likely be a part of what I do in the future. I love creating experiences through the built environment.
What Pro Tip would you offer to other CoS?
The two biggest things are —
- Hold the alignment with the organization in the highest regard. It's not about you. It's not about the other person. It's not even about an individual project. The question is what is the best thing for the company?
Honor and understand what the company's objectives and mission are and hold it in the absolute top regard. What I found is when I do that, making decisions becomes a lot easier. I don't have to think as much about what's the right thing to do in this situation. There's a lot more clarity that comes from having directly aligned interests with the organization. Anytime that I've found that I might have misaligned interests, I have to think through things a lot more to try to create alignment. And it's a waste of time, energy, and effort. There's a lot of clarity and efficiency and ease and productivity that comes from maintaining super alignment with the organization.
- The second pro tip would be around listening. This is something I’ve heard time and time again and I've realized more and more over the last 10 years. What does it mean to actually be a great listener? The first part is really believing people when they tell you something and brushing over what they said if it doesn’t fit your narrative or your understanding of the situation. I believe that before you can even start to listen to someone you have to put yourself in an open mindset and be willing to change your perspective in order to be fully receptive to hearing what they say.
I think that one of the most important things is asking great questions, knowing when the story isn't finished. Listening is kind of like a team effort. In order for me to be a good listener, I need to also proactively give you the prompts to share more.
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