Productivity

Small Business Corner: An interview with Jonathan Wasserstrum, the CEO and co-founder of SquareFoot

This article is one in a multi-part interview series with small business owners and experts to discuss their insights and recommendations on productivity, collaboration and business growth. The interviewer, Allen Gannett, is the author of the book The Creative Curve and is the Founder and former CEO of TrackMaven, a marketing analytics company. 


Finding an office space is rough. You have to tour countless offices, figure out your budget, negotiate with large landlords and then move in! 

Jonathan Wasserstrum started SquareFoot to fix that. The fast-growing company is using proprietary technology to make the commercial leasing process surprisingly painless. They combine their top-notch brokers with software that helps clients figure out what they need and where the best deals are.  

Even though Jonathan focuses on helping companies find their home bases, he’s recognized the power of remote work. We talked through how to build effective remote and distributed teams while ensuring a growth culture built on clear communication and efficiency.  


What have you seen as the biggest inhibitors of business growth, and how have you remedied those? 

It’s the biggest cliché, but people. Without the right people in the right seat, not all mission and vision aligned, you’re not going to go very far. When you start getting everybody on the boat rowing together, it’s pretty special. 

My Dad used to say, tell people what you’re going to tell them, then tell them that you’ve told them. It’s the repetition of it. Different people learn and process things in very different ways, which means it’s not just a matter of repetition, but it’s repetition across [the] medium. 

With seventy people especially, remote and distributed, not everybody’s going to process information the same way. There’s not a one size fits all for that.  

Because of this, from a technology standpoint, we put a big focus on figuring out what tools to use in order to most effectively communicate with our team, whether that be chat, email, so on.  

What is essential for productive teamwork, and why? 

Communication is at the heart of productivity, so having collaboration tools that help keep the communication open and accessible is key. We have an office in Belfast and NYC, so we rely on collaboration software to keep us all in sync. We [do] a ton of video conferencing and instant messaging. 

We [also have] twice a month All Hands where employees from the other offices call in. There’s a live stream of them to us, and us to them. It’s as if we’re sitting next to each other. We’ve grown the business from five to now more than seventy, and without productivity software, we’d be feeling our way through the dark.  

What do you think about the rise of remote work today? Do you feel it impedes productivity? 

I think remote work is awesome. When done well, it’s a boost to productivity. One of our employees wanted to move to Seattle for reasons separate from work, and it was a no brainer for us to say great, we want to keep you around. We didn’t really think twice about it. 

Technology has enabled us to build our company culture together, even in multiple locations. The nature of tech enables us to continue to collaborate when we’re not all next to each other. Without video conferencing, it would have been a lot scarier of a proposition for us to think about.  

How has the cloud helped maintain real-time connections and facilitate collaboration? 

Thankfully we have never really done anything without the cloud at SquareFoot, and honestly, I can’t imagine companies not doing everything on [it]. I think back to when I started my career fifteen years ago. If there was a spreadsheet that we were all working on, version control was worrisome. 

When we had to make edits to something, we would have to email it, download it, edit it, email it back. You didn’t know who had the pen at any given moment. Everything had to be done in series instead of in parallel.  

With the cloud, that’s a thing of the past. You don’t have to worry about what the most recent version is, because everybody’s able to collaborate in real-time, in multiple cities, even across seas.  

What is your go-to productivity hack?  

Do the most important thing you have to do that day in the morning. Otherwise, life always gets in the way. I’ll try and do it from my apartment before I even get into the office, because once I’m [there], there’s always something that needs attention. 

Somebody comes by my desk and asks, hey, do you have two minutes? Two minutes is never two minutes. It breaks up your flow.  

Task automation can be a huge aid for time management. What are some examples you’ve employed that have had the biggest impact on your business? 

On the marketing side, we do a lot of automated drip campaigns that we can tailor based on size of the client, the type of requirement, and what they’re looking for. It’s actually pretty cool how tailored you can make them. 

Further down our funnel, once a broker is working on a transaction, we’re able to automate a bunch of touchpoints and follow-ups. We can say, “Hey, you haven’t talked to this client in a couple days, should we be touching them?” 

Brokers also use it as a way to follow up with clients once they’ve closed a deal, and to make sure that we’re in front of them for the next deal. At every step of the funnel we’re using tools like that. 

As your company grows, how do you maintain efficiencies across teams? 

When we first started, there were five of us at a conference table. So we didn’t have to worry about how to communicate with somebody in another city—much less another country. 

As the company has scaled, we have [had] to figure out how to scale our communication. You have more people doing more things, so efficiency becomes even more acutely important. In that regard, we’ve become a lot more religious about using project management software, both within teams and between teams. 

When there’s a deadline, we all need to be plugged in. It helps keep everybody on the same page and aligned to what the goals are, which is imperative.  

What’s one piece of technology you couldn’t do your job without? 

My cellphone—it’s everything all in one place. On my way home, I can listen to a podcast, or read the paper. I can call my wife and colleagues, check my email, throw a meeting on the calendar. It’s crazy.  


People build companies, and what Jonathan highlights is that companies need to ensure the human foundation is solid, even if you are in a technology-centric business. When you build a culture with a strong foundation, you allow your company to scale.  

Jonathan and his team have built such a culture by focusing on hiring the right people, having clear communication, and finding efficiencies internally and externally. The result: A fast-growing company that is disrupting an antiquated space. 

But none of these processes are out-of-reach. Any small business can adopt similar practices. The key is to be intentional. 

You can’t wait for operations to break and then fix them. Great businesses get there by being ahead of the curve. 

Best of all? Process and communication are free. 

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