Working Remotely as a C-level Executive – Opportunities and Considerations

By Robert Adelson on 3 October 20   Executive Employment,Startups

CEO World Magazine logoThis article was publish in CEO World magazine on October 2, 2020.

Over the past decade, more and more business has been conducted remotely and that trend has only increased with the COVID-19 pandemic crisis. While the pandemic has done much harm to many businesses and the careers of CEOs and C-level executives in those businesses, it has also given rise to new opportunities, especially the chance to work remotely for those who do not wish to relocate to take a new executive position.

In recent representations, my executive client was a CEO based in Chattanooga, TN negotiating for a position in Texas, a CFO in Atlanta negotiating for a position in California, and another CFO in Connecticut negotiating with a virtual company whose CEO is in Florida, COO in Vancouver and manufacturing in New Jersey.

In a world where due to the pandemic both party’s conventions were virtual, where so many of our business meetings are via Zoom, the opportunity to take a position elsewhere in the U.S. and even around the world now presents itself without the need to uproot your life and family.

This article discusses this new world – the opportunities and challenges of working remotely for the CEO or other senior executives.

Dislocation and Change Brought by the Pandemic

During the months of March and April 2020, when the entire state of California was in lockdown due to the pandemic and to varying degrees complete and partial lockdowns went into effect in states across the country, businesses had to adjust to a new reality that executives could not come into the office.  The Zoom meeting and Facetime on your iPhone became the new way to “meet” colleagues.

Even many months later, as this article goes to press, in the Autumn of 2020, we remain far removed from the close proximity to colleagues which was the norm before March 2020.  If you commute into Boston, New York, Chicago, San Francisco and many of our major U.S. cities, they seem like ghost-lands with so few people walking the streets or populating the office towers compared to the pre-pandemic days.  So many executives are now working from home offices or suburban satellite offices!

Air travel too is way down. TSA checkpoint numbers averaged about 2 million per day in 2019 and right through February 2020.  Those numbers cratered at less than 150,000 for almost all of April 2020.  This Autumn, the number has climbed to an average of 500,000 but still remains less than 1/3 of the number in 2020. Thus, far fewer Americans have confidence in returning to crowded airlines to travel to distant destinations.

Certainly important parts of the U.S. economy have suffered severely. Restaurants, live entertainment, air travel, hotels have all suffered greatly, and industries closely related those have suffered as well.

Zoom meeting

Photo by visuals on Unsplash

New Meeting Opportunities via Zoom:  ENET example

Yet, as the saying goes: when one door closes, another one opens.

Because of the lockdowns and concerns over travel, we have all seen the rise of virtual meetings where executives participate from their homes or other remote locations, all gathered together in one conference on the computer or iPhone screen, where we all can see and speak to each other via Zoom.

This Zoom culture has given rise to new opportunities for Americans and others, too, from Europe, Asia, Oceania and the Third World to connect, which were little used or never attempted before.

My law practice these days is focused on CEO, C-level and senior executive representations in executive employment, equity, contract and tax matters – that is more than 90% of my law practice growth.  Yet, before that for many years, I had equal focus on representing founders or start-up companies.  Tied in with that business focus, for 10 years I was Chairman of the non-profit group Boston Entrepreneurs’ Network (ENET) ( where I am now Chair Emeritus but remain active.  Our group holds 20 meetings a year on different subjects of interest to tech and life science entrepreneurs (angel funding, co-founders, marketing, IP etc.), each meeting with three guest speakers on the chosen topic.

With our shoestring budget, ENET could never spring for travel or hotel for out of town speakers.  Now, we regularly have speakers who Zoom into our worldwide audience from their homes in California, Texas, Florida and around the country.  Also, ENET has a segment to begin each meeting, the “eMinute Pitch,” that allows up to three entrepreneurs to pitch their companies. Here too, we are getting entrepreneurs from outside New England who pitch despite the time difference – one founder delivered via Zoom an excellent 90-second pitch from his office in India!

New Client Get-Togethers via Zoom / DoorDash

Likewise Zoom has opened new opportunities for my law practice in the area of client entertainment.  When not doing the law, I enjoy eating and spectator sports.  Thus, I have or share season tickets to the Boston Red Sox, the Boston Celtics, and Boston University Terriers ice hockey. I would normally invite clients to dinner and a game for a “free legal get-together” where we can get to know each other better, the client can bring legal questions and I am off the clock – my “give-back” and appreciation for the patronage.  Well, with the pandemic, we can no longer attend Boston spectator sports.  So, over summer, I invited clients to “free legal get-togethers” at restaurants that offered outdoor dining that my wife and I were satisfied as socially distanced and safe.

With the colder days of Autumn now upon us, outdoor dining is no longer feasible, yet here again the pandemic has opened new opportunities. Beginning in November, I will be offering clients a free legal get-together over lunch or dinner via Zoom, where the client is at home or at his or her office, wherever that may be, and their meal is catered from a local restaurant of their choosing paid for by a DoorDash or Grubhub gift card I had purchased for that purpose.  Now, via my Adelson & Associates Zoom account, for the first time, my free legal get-togethers will reach out not only to my clients in New England but to so many of my CEO, C-level and senior executive clients who live and work in California, Florida, Texas, Georgia, Illinois, Ohio, NY, NJ, Pennsylvania and at other locations around the U.S. and even a few outside the U.S.

Bad News:   Pandemic’s toll on many C-level Executives 

That same principle, again due to the pandemic, of bad news and good news, hardships but also new opportunities, I am seeing applied to my clients around the country in terms of executive terminations and separations and then new job offers.

First, I mention those hardships and dislocations which are very real and for so many.

For many C-level executives, the COVID-19 pandemic has been a disaster.  In a recent article of mine, my focus was on CEOs and C-level executives who received job offers, had given their notice and just as they were to start the new job, saw their job offers withdrawn or terms changed because of the huge downturn in business, revenues and profitability due to the pandemic.  Certainly, there are many C-level and senior executives who have lost their positions due to a downturn in business, and still many others who have lost positions for other typical reasons like a new CEO who wants to clean house, and that new CEO uses the pandemic as a cover for his or her real motive to install their old crony in your position despite your exemplary past service to the company.

Losing your CEO, C-level or senior executive position in the pandemic can be devastating, especially so if you had recently relocated or for other reasons you are firmly anchored to your current location. Perhaps, you just bought your dream home.  Your spouse has an excellent position that he or she would not want to leave and perhaps he or she would not be licensed in that field in another state.  Your kids are school-age or perhaps have special needs and you do not want to further disrupt their lives.

Good News:  New Methods to Search Nationally for Your Next Position

Yet, here too, with employment separations and new job offers, just as in other examples I mentioned above with the expanding horizon of the non-profit group ENET and with my client free legal get-togethers soon to expand to clients of mine across the U.S., one door closes, and another door opens.  You have lost your position and don’t want to move again.  Well, in this era of the pandemic, you actually might be in a better position to improve your position in the next job, with much more expanded field of job opportunities and might not have to move after all.

Because executives are working remotely, because travel is harder, and because more companies are getting adjusted to using Zoom to stay connected, there are many new opportunities for CEOs and C-Level executives to interview for new positions and then assume new positions remotely without leaving their home or nearby home office.

My non-profit group, ENET begins this month to offer remote networking using the service Grapevine. (  Well, remote networking is also underway for CEOs and C-level executives seeking new positions. Each month, the Boston-based executive outplacement firm Stybel Peabody ( ) brings 30 board members from around the country to discuss some aspect of corporate governance using a case method approach.  ( These events provide excellent exposure for CEOs and C-level executives seeking to connect with Board members who might know of new openings for outplacement clients outplacement in the San Francisco, Dallas, New York and Boston metropolitan areas and for other major business centers  around the US.

New Job Opportunities for Remote CEOs

With the connectivity provided by the Internet, employers are more likely to look beyond their location to find the talent that they need. Indeed, businesses that offer flexible hours and remote work options are seeing higher retention rates. People want to work from home or wherever they are for the day. Employees who see flexible work at other companies may jump the fence and seek greener pastures. When you find a CEO position for a company willing to let you work remotely, you’ve found a forward-thinking company. So as CEO Rich Ward says, “When the war for talent is as fierce as ever, why limit yourself to the catchment area of your particular metropolitan area with rules around where and when people work?”

This may be your chance to get a step up in your career with a C-level job in Silicon Valley, in NYC or Research Triangle of NC, where you’ve always wanted to be, where there are big opportunities in your field, yet for some of the reasons said above or others, you are just not in a position to relocate your family.

Alternatively, if you are a sought-after executive from a major metropolitan area, you might consider an especially lucrative, intriguing or attractive job offer from a company in North Dakota, Mississippi, West Virginia or even Alaska or another place far removed from the urban centers of America – because you can take those positions and work remotely from Boston, Manhattan, Palo Alto, or wherever you live today.

Remote CEO Benefits and Challenges 

The benefits of remote work are numerous. Like other remote workers, the remote CEO will have more time with the family and spend less time commuting to the office. You can dress in comfortable clothes and work in the personalized comfort of your own home office.

Taking on a remote executive job has its challenges. It means that you will be leading from afar. You can work effectively as a remote CEO or C-Level executive only if you have the skills and experience to build and manage relationships and company culture virtually by interacting purposefully with co-workers through programs like Slack or having lunch Zoom calls. Can you be encouraging and supporting, are you able to inspire and challenge people to do their best in a virtual work environment? Surely your future employer would be looking for evidence of those skills. So when you are applying for remote jobs, you should highlight your remote skills and experience.

Negotiation Strategies for Employment Terms that Allow the CEO to Work Remotely

In negotiations to serve as a remote CEO or C-level executive, it is wise to enter such negotiations with flexibility to try to build the comfort level of your new employer as it accommodates to the idea of a key executive not on the scene and perhaps not even in the same time zone of the company’s principal office.

  1. Negotiate initial consulting to get to lead to your next CEO job offer
    One strategy for flexibility is to offer consulting.  My CEOWORLD magazine article on Consulting between CEO Positions describes the terms you should seek as a consultant.  But the bottom line is that if you get hired as a consultant to perform C-level tasks, after a period the company may feel comfortable making your position permanent with no change in your physical location.
  2. Negotiate for temporary relocation to build company comfort level
    A second strategy is temporary relocation. In the past, I have used temporary relocation, where terms are structured for the company to provide full funding for an apartment, car rental and weekly air commuting home, during the first year of service, before permanent relocation is required. That remains an option, where after a year, the executive may have established a value with the company, and it is now willing to allow the temporary relocation to continue rather than enforce a requirement for permanent family relocation that might cause the company to lose a valued executive who has demonstrated his or her worth to the company. The pandemic strengthens further arguments for temporary relocation because the executive will want to minimize plane travel for spouse and family for house-hunting and looking at new schools is typical in pre-pandemic permanent relocations.
  3. Use hazards of air and distance travel to reduce on site presence even with temporary relocation
    The third strategy is to use the pandemic, quite reasonably, to argue for reduced presence on site for yourself even with an agreement for temporary relocation.  So, that in the past where you might have commuted weekly, perhaps now, the commute and temporary relocation might be one week per month, so that air travel and exposure is reduced with the requirement for business class and perhaps, if necessary, the company pay for an empty side seat.My CEOWorld magazine article on executive employment agreement discussed terms to seek for your new position.
  4. Make executive compensation and equity concessions now to gain the remote position, with the expectation of being made whole in a later retention agreement.
    My 4th strategy for employment negotiations to secure a CEO position working remotely is offer some concessions in compensation, benefits and equity from what we might normally seek in the job offer, with the plan to seek more later.  My CEOWorld article on retention agreements discussed how you can leverage your success on the job – in this case as a remote CEO or C-level executive – to get the terms you would normally seek, once you have proven the results you are able to achieve while working remotely.
  5. Assure your remote contract provides requisite online connectivity and necessary tools to enable your remote operation
    Finally, in all cases, you would want your contract to provide for online connectivity and productivity tools to be implemented or enhanced in the company infrastructure, if it is not already sufficient. You may negotiate for staff with the right expertise to support the remote work environment as well. These would help to ensure your success in leading the company as a remote CEO.

In conclusion, your dream job may not be in your neighborhood but somewhere farther away, even much farther away. Don’t let that deter you. You have been working remotely due to the pandemic and remote work is here to stay even after the pandemic. Why not go for a remote CEO job now?