Going Remote? 10 CEOs Share How They've Scaled 100% Remote.

Going Remote? 10 CEOs Share How They've Scaled 100% Remote.
Larson Stair
These 10 CEO's share their insight on how they started and grew their business 100% remote and how you can quickly transition to remote

Times are tough and a rapid transition to remote work is never easy. Even at Demoflow we have been experiencing the trials and errors of remote work. In order to make remote work... work, we've decided to take inspiration from the experts and see how they've built their remote first companies from the ground up.

We created a list of the top 10 CEOs of remote first companies and shared their secrets to success.

These are hard times, so please share this with others so they can also adjust quickly and we can get through this together!

1. Automattic

CEO: Matthew Mullenweg @photomatt

Automattic is the company that builds Wordpress. Wordpress is touted to power 35% of all websites (even if they don't have a blog). Automattic was founded in 2005 and has since scaled to 940 employees that are 100% remote. The only offices they have are for board meetings.

From a conversation between Matt and Laurie Segall (CEO of and host of First Contact Podcast): 

"Leaders — just because you’ve always done things one way, doesn’t mean that’s the best way. When evaluating habits, try to focus on input not output. For example, if you normally have a weekly 9 am meeting in the conference room, that’s the input. How that meeting benefits the business, that’s the output. Is there a different input that will result in the output you’re looking for? These unusual times are a perfect time to reevaluate and reset."

Here are few other resources where you can read about Matt's personal productivity and remote learnings: 

  1. His personal website
  2. Productivity Tips From Matt Mullenweg
  3. Matt's Ted Talk: Why working from home is good for business

Laura Roeder

2. Meet Edgar

CEO: Laura Roeder @lkr

Meet Edgar is a social media marketing automation tool heared toward SMB's and has sent millions of posts to tens of thousands of accounts since 2014. Their team is consists of 12 individuals from UK to San Fransisco. Laura is also the founder of Ropig that helps quie the interrupting notifications that happen throughout the day.

From a conversation between Laura and Chris Ronzio (CEO of Trainual and host of Process Makes Perfect): 

"So something that we're always working towards is really limiting the number of one- on-one, private messages. We use slack like most remote companies do and we've found it problematic in the past, sometimes people will start private messaging a lot, feeling like, oh, I don't want to bother people, I don't want to create more noise in slack, but then you don't realize how valuable it is to just be able to peek in on other teams channels or for everyone on your team to see what you're talking about."

Here are few other resources where Laura has talked about remote teams: 

  1. Laura's Blog: Work From Home Tips & Tricks
  2. Why I Trust My Remote Team Completely

Wade Foster

3. Zapier

CEO: Wade Foster @wadefoster

Zapier is a tool to connect your tools to all your other tools to automate your workflow and not worry about writing code. Zapier was founded in 2012 with it's headquarters in Sunnyvale, California, but with over 250 employees located in the United States and 23 other countries (probably more).

From an interview with Chief Executive and written by Patrick Gorman:  

"We have to work on our communication. You’ve got folks all over the world. You can’t just duck into a conference room or catch someone in the hallway. So you have to be really disciplined about how you do the things that you’re going to do, whether it’s ship product, serve customers, market to customers, you have to build some process around that. You have to talk about here’s how we debate things, here’s how we communicate things, here’s how we raise issues. And that can be a bit different from how you do it in an office, so that’s a skill set that we had to hone over time."

Here are few other places to see what Wade has done to scale: 

  1. TechCrunch: Scaling a remote team up to 300 employees
  2. The Remote Show

Sara Sutton

4. FlexJobs

CEO: Sara Sutton @sarawsutton

FlexJobs is a remote job board that helps employees and individuals find flexible remote working positions. FlexJobs was founded in 2007 and now has over 75 employees located all around the world and has helped companies like Apple, Salesforce, American Red Cross and more scale their teams with remote employees.

From an AMA with Know Your Team written by Mandy Moore: 

"One of the biggest mistakes companies make when integrating remote workers is using “casual flex,” where the scope of the remote work program isn’t clearly defined, goals haven’t been laid out, hasn’t been thought through, and—most importantly—isn’t measured for impact. It’s great to be open to trying new things, and often trying an ad hoc remote arrangement a certain team member or team comes from a really good place… BUT, it’s rarely going to work well that way (for the team member or for the company’s culture)."

Here are few other articles where Sara has talked about remote work: 

  1. Queen of Remote Work: Q&A with Sara Sutton
  2. The Perks of Being a 100% Remote CEO

Jason Fried

5. Basecamp

CEO: Jason Fried @jasonfried

Basecamp is an all in one toolkit for working remotely. It is the premier project management and internal communication tool for remote teams worldwide. Launched in 2004 the company has grown to over 50 employees with over 3.3 million accounts created since then.

From the book he literally wrote (along with David Heinemeier) Remote: Office not Required:  

"Part of the problem is the perceived need to fill a whole day with management stuff, regardless of whether it’s called for or not. All those dreaded status meetings, interruptions for estimates, and planning sessions have a curious way of adding up exactly to a manager’s workweek. While monitoring output is sometimes quite important, it’s rarely a forty-hour-per-week position. Ten hours maybe, but few full-time managers have the courage to limit their presence to that."

If your company is tackling COVID-19 directly, reach out to for a comp'd account.

Here are few other areas to learn more from Jason Fried: 

  1. Periscope: Remote Livestream Q&A
  2. How To Make Remote Work, Work | Jason Fried

6. Close

CEO: Steli Efti @Steli

Close is a CRM for statrups and SMBs to drive radical transparency and provide a consistent 360 degree view of the company. Launched in 2013, Close has 40 employees working from 17 different countries serving thousands of customers. Even crazier, they have a minimum 7 week paid vacation policy and struggle with employees working too much.

From their very own blog on Remote Team Culture

"Every Monday, each team lead sends out a report that includes that week's goals and metrics. Usually, they share a Google Doc with everyone on the team. We all read each report, make comments, ask questions, and prepare for the team meeting. On Tuesday mornings, we have a company-wide video call, where we typically have follow-up discussions based on Monday’s reports. These calls are scheduled for 30 minutes, but most only last 15–20 minutes. We also make sure to record these meetings, so that anyone can review what we discussed... (Read More)"

Here are few other posts from Steli: 

  1. LinkedIn: Remote Work Activities
  2. The Keys To Maintaining A Great Culture Within A Remote Sales Team

Clark Valberg

7. Invision

CEO: Clark Valberg @ClarkValberg

InVision is a digital product desgin platforms powering the world's best user experiences. Founded in 2011, the company now has over a $1 Billion Valuation and over 900 employees located across the globe.

From an interview with titled "Culture By Design":

"Use the Right tools. Consider the amount of time spent gathering people physically for meetings. People run late, dip in and out of the conference room, and have to quiet down before diving into the agenda. Whereas, tools like Zoom enable people to start meetings within seconds and allow everyone to take advantage of any dead time in between. “If I’m five minutes late to call you, you don’t have someone waiting and twiddling their thumbs doing nothing,"

Here are few other areas to hear from Clark and Invision: 

  1. This Software Company Has A $1 Billion Valuation, 800 employees, and Zero Offices
  2. All 700 employees at this startup work remotely

Sid Sidbrandij

8. GitLab

CEO: Sid Sigbrandij @sytses

GitLab is complete DevOps platform from project planning, source control to CI/CD and monitoring for software projects. Founded in 2011 GitLab has over 1100 employees 100% remote from across 65 different countires.

From their very own GitLab's Guide To Remote Work (Emergency Plan):

"While functioning remotely, strip the tool stack down to a minimum. Google Docs, a company-wide chat tool (like Microsoft Teams or Slack), and Zoom are all you need to start. If your team needs access to internal systems through a VPN, ensure that everyone has easy access, and instructions on usage are clear."

Read The Entire GitLab Manual:

  1. All Remote Guide To Remote Work
  2. Remote Without Warning (Streamed Mar 2020)

9. Doist

CEO: Amir Salihefendić @amix3k

Doist is the 100% remote company behind Todoist and Twist, before productivity tools for teams and especially remote teams. Founded in 2007, Doist has over 68 team members from Taiwan to Poland and have helped users complete over 1.6 Billion tasks.

From a tweet thread Amir Recently published:

"Remote work isn't exceptional as companies that are spread around multiple offices have done it for the last many years. The special sauce is communicating asynchronously as the default."
"Blocks becomes a non-issue as you are blocked by default. Everyone knows how to spend time productively while waiting for an answer."

More from the Doist Blog and Amir himself:

  1. Asynchronous Communication: The Real Reason Remote Workers Are More Productive
  2. Remote Teams Are The Future

10. Know Your Team

CEO: Claire Lew @clairejlew

Know Your Team is a leadership software to help leadership hold effective one-on-ones, get feedback, share progress, and build team rapport.

From their Guide To Manage Remote Teams:

"Based on our survey we conducted with almost 300 remote managers and employees, insights from our online community in Know Your Team, The Water-cooler, and what I personally strive to practice as a leader, here are the 4 biggest things that remote leaders do differently... 1. Switch from "Speak first" to "Write First" 2. Trust your employees... for real. 3. Get intentional about social connection. 4. Have the hard conversations, quickly"

More from the Know Your Team Blog and Claire:

  1. A Guide To Managing Remote Teams
  2. Interview with Founder + CEO of Balsamiq (Another 100% remote company)

Key Takeaways

From reading and evaluating all of the advice these individuals have provided, a couple of key things stick out.

  1. You must be deliberate with your communication
  2. You must be deliberate with your interactions with employees
  3. You must trust your team to do their work
  4. You must accept that you won't know everything and that things will happen when they happen.

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