5 things being an Upwork founder taught me about all-remote

My passion for all-remote teams began in 2003 when I founded oDesk/Upwork with my childhood best friend. At that time he was in Greece and I was in California, which inspired us to create a company for remote workers. Today, I’m aware that founders who are embracing remote work face many practical challenges. I started this blog as a platform to share with other founders the lessons I’ve learned from 16 years of building remote teams and companies.

This first post covers the main takeaways from my time at oDesk/Upwork and how I’ve used my learnings at my current company Ergeon.

1. All-remote is easier than part remote

While I did not have the courage to go all remote at oDesk, I realized that in many ways it’s a lot easier to be all-remote than part remote. My current company Ergeon is all-remote. We have 50+ team members in over 20+ countries. Our Palo Alto “office” is a small conference room with phone booths. The Bay Area staff spends 50% of our time at home or at coffee shops. In one year, our team grew 5x and we did it without experiencing the typical delays due to finding local staff or the need for more office space. The all-remote model also safeguards us against the risk of isolating remote staff in the case of part-remote companies. Typically I have seen companies start all-remote, but as they grow they start hiring local executives. When your senior managers are all local, your corporate culture can quickly slip into the dynamic of headquarter staff vs. remote staff. This can devolve into the remote staff feeling like second class citizens. When everyone is remote, your organization is truly flat and inclusive.

2. Ask people how they feel
When people are co-located, a manager can easily walk around the office and sense the energy level of each team member. This isn’t possible when you are all-remote. You could live stream everyone’s workspace but I am against ‘Big Brother’ surveillance. It can be tough to feel the pulse of your remote staff, but it’s possible to overcome. At Ergeon, I regularly ask my engineering team to share their feelings on a scale of 1–10 to gauge their energy level. I have weekly one-on-ones with my direct reports and fireside chats with the entire team to stay connected. We also use an app called “Leo bot” to conduct employee surveys to help uncover issues related to compensation, job satisfaction, stress, and physical health. I was initially skeptical of these tools and tactics when my cofounder introduced them. Now that I see the positive culture this creates, I wish I had been doing this sooner.

3. Video is the biggest enabler of all-remote

In 2003 there weren’t enough powerful laptops, phones, global broadband penetration, and mature collaboration technology to facilitate an all-remote organization. The only possibility was an all-remote engineering team. Since then, there has been a proliferation of web-based tools (Slack, Trello, Google Meet, Amazon Cloud) that are incredible for collaborative work. Still, video stands out as the only technology that allows people to interact ‘face to face’. Video communication has made huge improvements over the past 16 years. Now Google Meet has amazing new features, such as a tiled layout so you can see multiple faces enlarged, dual-screen sharing and presentation, recording capability, and concurrent audio from multiple participants. It has allowed a much deeper personal connection between people even when they have never met face to face. Of course, I look forward to AR/VR being readily available and taking this one step further.

4. Time zone is a real challenge

At Upwork, many of our engineering talents were based in Eastern Europe. Our biggest headache wasn’t due to different cultural norms or English communication. Instead, time zone differences were a major challenge. At first, I asked the Engineers to follow our US business hours, which meant they had to work until midnight their time. This approach caused burn-out and affected long-term retention. I have since learned to be more flexible and considerate of a remote worker’s time zone. At Ergeon, engineering meetings happen between 6–10 a.m. PT to facilitate a more agreeable time for remote workers. As an added benefit, I can push out a feature during my business hours and have it done when I wake up the next day!

For remote functions like sales, operations, application and QA engineers, which all need to be responsive to vendors and customers, I have had the most success hiring from similar time zones as my business hours.

5. Apply best practices from large distributed companies

I used to think large companies have nothing to teach remote companies. More recently, I realized that in order to build a successful all-remote company you have to implement the processes designed for a much larger workforce as early as possible. I’ve applied this idea to Ergeon; for example, even when we were just 10 people, we held All Hands, Quarterly Reviews, documented processes, and ran boot camps for various functions. Most startups begin implementing these practices after they reach 100+ staff members. To my knowledge, no all-remote company has grown beyond 1000 staff members, and if our ultimate goal is to grow to the size of a public company, we will need to consult the public companies with 10,000+ staff for best practices. Of course, much still needs to be adapted for the remote context.

The tools and processes used for building all-remote companies have come a long way. In future posts, my co-founder and I will discuss more specific topics around all-remote work such as:

• How to upskill people remotely?
• How to pay engineers in different regions?
• How to transition from office worker to remote worker?
• How to work effectively given time zone differences?
• How to keep remote teams productive?
• How to source remote workers when LinkedIn fails us?
• How to give stock options to a remote team member?
• Why stock options are important for a startups’ remote team?
• How to build personal connections while being a distributed company?
• How to operate without a physical office?

Interested in any of the above topics? Be sure to follow us here to be notified when a new post is published. I also welcome your feedback, comments at Hacker News.