Working Remotely 101 : the beginner’s guide to building a successful remote startup 2021

As we have transitioned to working remotely, I have been reflecting on how we can be more effective given the new reality, and turn that into an advantage.

While some companies have done exceptionally well when working remotely, most do not have an effective system to address the sudden changes COVID brought to many of us.

In the past several weeks, I have been studying examples of pros at remote work and wanted to share my learnings.

I believe that most companies will end up with a hybrid model (remote + office), but it’s still worth exploring how to leverage working remotely better.

Working Remotely: Man holding his head while sitting on chair near computer desk

We will cover the following topics on working remotely:

Examples of successful remote companies

Some companies have products that encourage remote work. Think of Slack or Zoom. Working remotely at those companies gives you the ability to use the product every day, constantly improving it not just for your clients but for yourself as well. Yet, not all companies have so well aligned products and company structures. Think of Zapier, it could have been easily a regular company with a few offices, yet they decided to be remote from day one:

1. Zapier - is a 100% distributed company with over 300 remote employees in 17 time zones and 28 countries.

“From day one, Zapier has always been a distributed team. Even though my co-founders, Bryan and Mike, and I lived in the same city, we had different schedules and were bootstrapping Zapier on the side of our day jobs and school. We worked on Zapier in every spare moment we each had, but those moments didn't magically line up at the same time where we could work in the same room. Plus, side projects can't afford offices. So we just worked from our apartments, coffee shops—wherever we could get things done.”

Wade Foster a Co-founder and CEO at Zapier

2. GitLab - is the world's largest all-remote company with over 1,300 team members located in more than 65 countries worldwide.

"Remote is not a challenge to overcome. It's a clear business advantage."

Victor, Product Manager, GitLab

3. Unity - recently transitioned its global workforce of more than 3,400 employees to a work-from-home environment.

“We mobilized around 50 people literally around the world, who worked in offices on a Friday, and started all of our employees working from home that following Monday.”‌
‌‌
‌Amanda TaggartGlobal director of PR, communications and events, Unity

4. Buffer - is a fully remote team spread across the whole planet. They have employees in 15 countries, 11 timezones, and 42 cities.

“Our distributed team setup at Buffer is a result of our vision to create a workplace of the future and around our value to live and work smarter.”

Joel Gascoigne CEO and Co-Founder of Buffer

Tips for working remotely

1. Slack

Since we use Slack to communicate internally, I could not write this post without sharing some tips for working remotely by leveraging Slack as a tool.

How to use channels?

Channels are where work happens in Slack. If you are not familiar with Slack, think of them as dedicated spaces for teams to discuss and work on specific topics.

Naming your channels appropriately can help new and old employees to identify what they need quickly. We recently started following the structure Slack recommends:

Working Remotely: Examples of effective channel prefixes in Slack
Examples of effective channel prefixes in Slack

Use emojis for fun, empathy, and emotion 😎👌🙏👀🙈

In today’s highly decentralized work environment, the use of emoji helps teams to communicate emotions. As we do not have visibility to each other’s body language at all times, emojis help us understand how we feel about different announcements. It’s especially valuable when praising people:

A very public happy birthday message
A very public happy birthday message

Tag people

On a busy day, colleagues end up engaging you in discussions across multiple channels. The only way to make sure everyone reads your text is by tagging them on each message. A simple yet effective method we discovered way too late 🤦‍♂️ .

Example of how to support and celebrate your team within Slack with emojis
Example of how to support and celebrate your team within Slack with emojis

2. Establish daily check-ins

In my experience, establishing daily check-in calls helps teams coordinate with each other and feel more connected. The key is to establish video calls that are regular and predictable. Employees must feel that they can consult with the leadership team and that their concerns/questions are heard and addressed.

3. Encourage social interactions

As we are suddenly living in times where nearly all non-work items are excluded from our regular workdays, it’s important to encourage social interactions.

“When you don't see people in person, if they're not broadcasting how they're doing, you won't know. You miss the little hallway conversations where you hear about the antics of someone's children or pets. You can't see the things that might cue you in when someone might be stressed or sad about something in their personal life, or even upset about something at work.

That means you have to ask.”

Janine Anderson Managing Editor of the App Directory at Zapier

From starting each call with a few minutes to catch up with each other, all the way to facilitating events where people can eat and drink together, i.e., virtual office parties. While, at first glance, such events may seem silly, experienced managers report that such initiatives reduce feelings of isolation while promoting a sense of belonging.

Additionally, you can start Slack channels (or whatever platform you are using) for “random” interactions. We recently set up an automation that pulls a funny GIF from the internet and pastes it in our “random” channel on slack to kickstart some funny discussions.

4. Establish remote work playbook

To ensure consistency in behavior across different time zones and cultures, you will need to establish a “single source of truth.” Communicating and updating such a playbook is a never-ending process. In my experience, Notion is great for documenting such an e-book.

One of the most sizable challenges when going remote is keeping everyone informed in an efficient way. Put concerted effort around systematically documenting important process changes in a central place to minimize confusion and dysfunction.‌
‌‌
‌Darren Murph, Head of Remote at GitLab

5. Virtual meetings, rules of engagement when working remotely

As you are transitioning into a remote work environment, you will need to establish engagement rules during meetings.

Unless my internet happens to be terrible, I have made a point of keeping my video always on. My impression is that a video-on rule encourages more attentiveness as your colleagues cannot multi-task with the video on.

Muting notifications is another simple yet important rule to help you run the meeting more effectively.

For recurring meetings, you can run a poll on Slack to find out if people find it effective; here you go, an example from Toptal:

Digital tools to help you work remotely

As you are working remotely, it’s easy to end up using a ton of digital tools. While I test new tools every week, I rarely end up using them in the long run. More tools add more complexity, so strip the tool stack down to a minimum.

In our case, the few most important tools are:

Benefits of working remotely

The rise of tech startups and innovation has made remote work possible. Yet, a decentralized team may not be the perfect solution for everyone. In my opinion, most companies will figure out a hybrid model to tap into both worlds' benefits. Yet, the benefits of remote work are undeniable; here you go a few examples:

1. Reduced costs

Factors like long commutes due to an increasingly expensive cost of living in major tech hubs have accelerated remote work transition.

“I no longer need to rush in the morning to catch a train/bus. I do not need to suffer in a very crowded train rides of Tokyo. I do not need to worry or feel anxious about being on time when there is a delay (trains and buses). I am more in control of my schedule (e.g. when to wake up, eat, work, play, cook etc). On the other hand, you need to be disciplined because no one is managing you.”

Keita Yamada, Customer Support Specialist, Doist

2. Access to top talent and remote jobs

If you are based in a major tech hub like Singapore, it can be tough to attract top talent. Your competition is the worlds’ most successful brands that often have more resources than you do. On the other hand, if you are building a company in a less popular hub, it might be difficult to persuade prospective employees to relocate there and adapt their lifestyles. In our case, working remotely, we can tap into talent across entire Southeast Asia with employees in Indonesia, Malaysia, the Philippines, Singapore, and even Bulgaria. In turn, we have transitioned almost all of our opportunities to “remote jobs.”

“Remote teams almost have an unfair advantage in hiring. I regularly talk to San Francisco teams that lose candidates because other companies offer an opportunity to work from wherever they want. This has become more and more common.”

Andreas Klinger, Head of Remote at AngelList

3. Environmental benefits

According to Global Workforce Analytics, if remote work compatible roles decide to work half the time from home, would create the following annual savings:

  • $20 million in gas
  • 54 million tons of greenhouse gas emissions (equivalent to taking almost 10 million cars off the road for a year).
  • 640 million barrels of oil (worth $64 billion)
  • 119 billion miles of highway driving

Common problems of working remotely

Unfortunately, for all its benefits, remote work comes with some common problems. A fully decentralized organization presents challenges, and not every company can address them adequately:

1. Communication

Transitioning to a 100% remote environment comes with more opportunities for miscommunication. Instead of casual chats, people need to articulate their updates and challenges in a written format clearly. Not everyone adapts to that quickly, and even if you do a great job at communicating concisely, you have not idea if the person on the other end will rea, let alone understand your message.

“A big challenge was projects taking twice as long to complete because of time zone differences. My designer was in Australia and my developer was in the Philippines, so if I outlined an ask, I had to be very specific about why we needed something, what I wanted, and what examples already existed. If there was a question, I wasn't online at the same time to answer it. I had to become adept at providing detailed instructions, and mocking up what was in my head.

Juliana Casale, Former Head of Marketing, Crazy Egg

2. Loneliness and isolation

Remote work eliminates almost entirely happy hour drinks, chatting about the weekend, and catching up personally with different colleagues. As a result, it’s harder to connect and build trust.

“Remote work gives you freedom, and with that freedom comes the burden of loneliness. Working from home means, in many cases, that you work alone. The challenge that presents for us is that it can turn some candidates away. We’ve lost people because they realized remote work isn’t for them. Not many, but it does happen, and it’s something companies should prepare for.”

Devin Bramhall, Director of Marketing, Animalz

3. Company culture

From a leadership perspective, working remotely presents many challenges when it comes to fostering comradery and tight company culture. Building trust, communicating objectives, addressing challenges, setting the right examples becomes much harder and requires a dedicated effort. Early-stage companies may find it difficult to allocate extra resources for such activities.

“I still don’t think we’ve fully solved the culture equation. Companies have augmented remote interaction with in-person meetups and a suite of collaboration tools, but I still think we haven’t found a way to build relationships across remote teams effectively. I think the biggest gap there is that most solutions try to copy and paste what works in an office, instead of coming up with new solutions for this new workforce.”

Steph Smith, Head of Publications, Toptal


As we are now well into the pandemic, the pros and cons of working remotely are getting clearer. Cultural norms and tech barriers are now broken, setting in motion a new reality where more and more companies will either give a try to remote work or adopt hybrid models. We are not an exception and I am looking forward to embracing a new hybrid model that allows us to take advantage of both worlds.

Over to You

I’d love to hear about your perspectives on remote work by dropping us an email at hello@greenhouse.co.

  • Do you do remote work at your company?
  • What are your learnings around building the organizational culture at a remote business?
  • What are your tips for working remotely?
  • Do you offer remote jobs?
  • How does your organization define the concept of work(ing) remotely?
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