Interview: The Future of Work

Amitree founder and CEO Jonathan Aizen shares lessons from going all-in on remote work

Like many Silicon Valley founders, Amitree CEO Jonathan Aizen spent much of the past year navigating both a shift to remote work and a painful reorganization. Though in his case, the pandemic had nothing to do with either decision.

In October of last year, months before the global pandemic got underway, Aizen gathered his 25-person team at their San Francisco headquarters to announce the company was going all-in on remote work. He’d shutter the expensive office and restructure the team (those who left did so with generous terms) and hire a new, global staff.

“That was easily my hardest day as a founder,” said Aizen, who’s started three companies and steered one through the Great Recession.

That day also marked a crucial turning point for his fledgling company, which is now cash-flow positive. Aizen manages a team of a dozen people across nine countries from his home near Tel Aviv. 

He learned a lot about what works — and doesn’t — when building remote teams and shared some of those lessons with us.

Russ: How did you first get interested in tech?

Jonathan: I’ve been a technology entrepreneur pretty much my whole life. I’ve always loved the process of understanding problems people have and figuring out how to solve them — and delight them in some way. My dad taught me to code when I was 8. My parents were both psychologists, and the first program I wrote was like a virtual psychologist that would ask you questions about how you’re feeling and spit back random answers. It would probably sell in the COVID age. 

Russ: What was the origin of Amitree and your core product, Folio?

Jonathan: When my wife and I were buying our home, I observed that our agent — who we loved — spent a significant portion of his time on tedious, administrative project management tasks.

I quickly realized this wasn’t just a real estate problem; it’s a modern work problem that most of us have. It’s a consequence of inefficiencies in the core tool set that people use to do their work, and it’s particularly acute for complex process managers — real estate agents, architects, event planners, divorce attorneys — who have to coordinate relatively complicated processes with a lot of stakeholders all working at different companies.

We created a machine learning algorithm that functions as a workflow compression tool. Today our system is used in almost 40% of all the residential real estate transactions in the U.S., and we’re expanding to new markets.

Russ: You decided to transition your company to an all-remote workforce well before COVID hit. Did you have a crystal ball telling you remote work was the future?

Jonathan: (Laughs.) Hardly. When we started the company, I asked my co-founder to move to San Francisco from the East Coast — that’s how strongly I believed in the need to all be together in the same room sharing Post-it notes and enjoying the benefits of serendipity. 

It didn’t take long for us to bump into problems. For one, my co-founder wanted to get back to his life in New Jersey. Also, we had a hard time building a team because it was so competitive in San Francisco.

I started thinking, “We’re building this thing that's supposed to usher in the future of work, and this doesn’t feel like the future of work.” San Francisco used to be the center of the universe for startups; it feels increasingly less so. 

I started to experiment, hiring people in different areas and building a hybrid team of remote and on-premise employees. That brought its own problems, as employees in San Francisco wanted to work remotely, too.

A little over 14 months ago I went to the board and said I wanted to do something radical: I wanted to build a team globally, sourcing the best talent we can find. In the meantime, we’d realize the cost benefits by focusing on areas with great talent and a reasonable cost of living.

Russ: How did you figure out your plan?

Jonathan: We interviewed CEOs who built remote companies using all types of models. Ash was really helpful in making introductions.

At the time many of the companies shifting to all-remote were bootstrappers that hired patchwork teams in different areas to save money. It was all about cost to them. But we also found people like Thejo Kote, CEO of Airbase, who did it to hire the best possible team without being tethered to geography or the inefficiencies of office work that have come to the forefront since COVID. 

I also read everything I could find, including Gitlab’s Remote Manifesto, which has a lot of great information on the different models out there. 

Russ: Looking back, what early decision proved crucial to your success?

Jonathan: Pretty early on we decided we wanted to be a fully asynchronous team, which means we don’t need live conversations to get our work done.

The whole process of ideating, developing, understanding, designing, creating, and shipping software happens asynchronously. We serve customers that way, too. 

If you are an engineer, you should be able to wake up whatever time you want and be able to do your work without having to ask questions that you need an immediate answer to.

We learned from Air Base how to make our employee onboarding process asynchronous, too. It’s all written down and self-directed. It gives them exercises to do it and quizzes along the way. Instead of me sitting there showing them how to look up our MRR, the document tells them how to do it and tests them later. It works incredibly well.

Russ: Why did you decide on such an extreme route?

Jonathan: Our goal was to tap the best talent no matter where they are in the world. You can’t do that if your employees need to be able to talk to each other all the time to get their work done — because then everybody has to be within three hours of each other and it defeats the purpose.

Russ: What’s the biggest challenge you confronted in the shift?

Jonathan: The switch to asynchronous communication has been a big one. It’s like a new muscle we need to develop. There’s so many times you want to say, “Let’s just jump on the phone.” 

Like anything, if you invest in it, develop it, and you prepare to be good at it, you will be good at it.

Russ: How has the experiment worked out with employees?

Jonathan: It’s worked out extremely well. We reset the team and the cost structure, so that the company can be long-term sustainable. We’ve also ushered in a new way of working along the way. 

It’s not without its challenges, of course, but we’ve built a very talented team that works well in this environment

I hear from new employees all the time, “I was skeptical, but wow, it’s changed my life.” It’s unbelievably liberating to have control over your own schedule. I can stand up in the middle of my day and ride a bike to a bakery without worrying that I have to check Slack every second, because if I don’t somebody will think I’m not working or won’t have what they need to get their work done.

One of the biggest benefits to being asynchronous is that the stress level is like a tenth of what it was before — and we’re more productive. I’m much more focused on my work and thinking, as opposed to back-to-back meetings. In most meetings, 70% is a waste of time, 10% is relationship building, and 20% is getting work done. We cut out that 70% and get that time back.

Russ: Did you achieve the financial reset you were hoping for?

Jonathan: Yes, absolutely. We’re now cash-flow positive, and that means we have unlimited runway and can use our capital as we see fit.

This shift has allowed us to grow rapidly without being stuck in a never-ending fundraising cycle. We did a $10 million Series B. In our new world, that’s the last round we’ll ever need to raise, unless we decide we want to raise more.

Russ: What’s it like to manage a fully asynchronous team?

Jonathan: It requires a lot of trust in employees that they’re not going to take advantage of you.

Frankly, I don’t know what my employees are doing all day long. I don’t know what hours they’re working. Most of them end up doing incredible work, which is all I really have to base performance on.

One of the biggest switches I had to make was to stop equating responsiveness with engagement and quality work. I can only look at outputs. Do I see you generating code that works well? Is the product manager happy with what you’re doing? Do the customers feel that the customer care manager cares about them?

I think that the trust I put in them motivates them to work hard and deliver; it makes them proud of the work they do. I think it makes them happy to be with the people who are there because they’re trusted, respected and valued.

Russ: Where do companies get remote work wrong?

Jonathan: I think what’s soul-crushing for so many people who’ve gone remote in response to COVID is the feeling that they’re on Zoom calls all day long. They’re working longer hours and dealing with more stress because it’s not asynchronous. Companies are trying to replicate the in-office experience over Zoom, and it doesn’t work. Managers aren’t trusting them to do their work, so they’re creating more touchpoints.

I’m not saying everyone should go asynchronous; there’s a range of models out there. You just have to rethink what you’re doing and be intentional about the processes you create.

If you just go about it blindly switching out of the office and onto Zoom, you’re going to struggle.

Russ: What advice do you have for founders contemplating a move to all-remote?

Jonathan: First, you need to figure out how asynchronous you want to be. There are various models out there — not everyone is going to want to go as extreme as us.

Try to unlearn much of what you already learned, because things are going to work pretty differently. Take advantage of resources like the Gitlab guide and other CEOs who have gone through it.

Explicit, clear written documentation is key. It’s about reducing the need to go back and forth.

We try to get people in a default mode of editing their thoughts before they share them. We like people to be very explicit when there’s something they need. It reduces the stress of not knowing what someone means and allows more time for people to take their time and be thoughtful about what they are doing.

We use public channels in Slack instead of private one-on-one messages, so that other people in the future can find the conversation. We are adamant about using the threads feature on Slack.

Russ: What’s it like working with Ash at Morado Partners?

Jonathan: Ash has this really nice mix of both support and healthy skepticism.

So many times he encouraged me at the same time as he helped me prepare for the inevitable challenges and failures I’d confront. He can see things coming long before there’s any signal.

He helped me understand the baseline expectations from venture investors at any given round of financing. He’d say, “Here’s what people might be looking at, and here’s why it might be hard to get there given your current strategy.”

A lot of times when you hear critique from an investor, they’re telling you why they don’t want to invest. With Ash it was, “I’m going to invest — and here’s where I could see you bump into a challenge, so you can keep it in mind as you move forward.”

Morado has also been incredibly supportive as we made that shift to remote work. They connected me with so many different people who helped pave the way for us.