CEOs Are Moving To Remote Teams and It’s a Win for All of Us

By Jordan French Jordan French has been verified by Muck Rack's editorial team
Published on December 12, 2019

While remote work has certainly been on the rise in the last ten years, especially among millennials and “digital nomads,” it could very soon even become as common, if not more common, than working in an actual office.

What started as a trend of outsourcing to remote executive assistants has morphed into entire companies of thousands of employees, e.g. WordPress and Github, working remotely. The decision by corporate leaders to go “remote” isn’t purely out of magnanimity either — research shows that productivity and profitability can skyrocket thanks to many benefits of allowing employees to work remotely.

But Why Can’t Every Company Work From Home?

To be sure, not every single company can work from home, and measures do need to be taken to remain productive while working at home.

But what’s very clear is that the future of building very large companies, especially tech unicorns, could largely benefit from CEO’s utilizing remote teams. To get a better understanding of how the benefits of remote work look for both CEO’s and for the rest of us who work for them, as well as what opportunities it could mean for working as a freelance or gig economy digital nomad, we sat down with Ethan Bull, co-founder of ProAssisting.

After working as executive assistants for high-powered CEO’s of major corporations in New York, Ethan and his wife, Stephanie, made the switch to a remote lifestyle. They founded ProAssisting to help provide remote executive assistants for large corporations, startups and high profile public figures.

The Driving Forces Behind Remote Work

GD: What do you think are the driving forces behind CEO’s increasingly gravitating towards remote teams?

Ethan Bull: First, technology has made communication instantaneous, friction-less and closes the geographical gap between CEO’s and their direct reports/teams.

Second, as remote work has been studied more, it’s proven that remote workers are more productive. When an employee is able to create their own work/life balance and has no commute, they work outside of normal business hours and feel a sense of reciprocity toward their company and boss for such flexibility. This leads to more productivity and better work product.

Lastly, since businesses are using the Internet to reach out to a wider and more geographically diverse customer base, CEO’s are taken out of and further away from their own offices more often which makes the locations of their teams less relevant.

GD: Why is it advantageous to utilize a “remote executive assistant?”

EB: The biggest benefit to using a remote executive assistant is having a much larger pool of high-level and talented candidates to choose from versus the restriction that a geographical location has on such a search.

By working with a more tenured and experienced executive assistant in a remote fashion, the principal will still get their “outside-the-box” thinking, their “figure-it-out” attitude and their emotionally intelligent affect even though they don’t work in close physical proximity.

Also, top-level executive assistants understand that they work for the leaders of their companies and that time will need to be spent working outside of normal business hours.

By having the flexibility to manage their work/life balance and not having to commute into an office location, they are more adept and available to accommodate such responsibilities.

GD: What can be some disadvantages to utilizing a remote support team?

EB: A remote executive assistant can’t get your coffee or lunch or pick up your dry cleaning without involving a third-party service or an additional employee to close that physical gap.

Additionally, not all executive assistants have the discipline or disposition to work remotely and candidates need to be interviewed and selected accordingly.

Lastly, while we haven’t seen an issue in regards to creating a strong working relationship between a remote executive assistant and their principal, the remote executive assistant has to take special care to create strong working relationships with the other people on the team and within the company that they interact with regularly.

Taking communications to phone and video conference versus just email goes a long way to forming and solidifying those relationships.

How Founders Prepare for Virtual Teams

GD: How can a company that has traditionally utilized on-site hiring, transition to a “remote” atmosphere?

EB: Before engaging a remote executive assistant, the principal needs to have an honest self-assessment about how they work with their onsite executive assistant.

Are they always running late and need an assistant to knock on their office every five minutes to keep them on schedule?

Are they constantly adjusting their schedule at the last minute and need “by-your-side” support to facilitate those adjustments?

Do they want a gatekeeper to be physically present in their office suite to provide a buffer? If they can take responsibility for those aspects of their working style, they can easily transition to remote executive assistant support.

GD: What are some of the higher-level responsibilities your own firm has had delegated to it by clients that previously may have been reserved for on-site staff?

EB: We view high-level executive assistant support as a combination of project management, chief of staff and executive assistant roles. The project management and chief of staff aspects of the role took us from the office to homes, other businesses and the scouting of locations for events and meetings.

As remote executive assistants, we supplement those location/venue scouts, meetings with contractors on location and such with cellphone to cellphone video conferencing. When needed, we’ll take screenshots of these images to then show the principal and discuss options.

Some of the Biggest Players in Tech Embrace Remote

GD: Can you give an example of a company that you believe “gets it” when it comes to utilizing remote teams effectively?

EB: Matt Mullenweg and what he has built with Automattic, the parent company of popular online publishing platform, WordPress — and a wonderful example of what a company can do when they are built on the principal of remote work.

A complete remote work company valued at multiple billions of dollars powered by 100% remote workers. They rely on technology to keep everyone on the same page and are able to get the best-of-the-best talent regardless of location. If ProAssisting uses that as our North Star, we’ll be just fine.

How Do Millennials and Gen Z Play Into Remote Infrastructure?

What’s might be most interesting is that there is (unsurprisingly) a generational gap of sort that needs to be mentioned in a discussion about remote work.

The trend popularized significantly under millennials. However, gen Z could reshape the meaning of work on a whole new level, with many of them not even considering onsite office positions.

Could the days of cubicles and water coolers finally be ending?

By Jordan French Jordan French has been verified by Muck Rack's editorial team

Journalist verified by Muck Rack verified

Jordan French is the Founder and Executive Editor of Grit Daily Group, encompassing Financial Tech Times, Smartech Daily, Transit Tomorrow, BlockTelegraph, Meditech Today, High Net Worth magazine, Luxury Miami magazine, CEO Official magazine, Luxury LA magazine, and flagship outlet, Grit Daily. The champion of live journalism, Grit Daily's team hails from ABC, CBS, CNN, Entrepreneur, Fast Company, Forbes, Fox, PopSugar, SF Chronicle, VentureBeat, Verge, Vice, and Vox. An award-winning journalist, he was on the editorial staff at and a Fast 50 and Inc. 500-ranked entrepreneur with one sale. Formerly an engineer and intellectual-property attorney, his third company, BeeHex, rose to fame for its "3D printed pizza for astronauts" and is now a military contractor. A prolific investor, he's invested in 50+ early stage startups with 10+ exits through 2023.

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