These 10 CEOs Share Tips and Benefits to Working Remotely

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Working remotely has become a growing phenomenon in the last few years and for good reason. Not only does this work style offer employees the flexibility they constantly seek, but also a great opportunity for employers to save on overhead costs, decreases sick days and employee time off, reduces stress and increases the employee talent pool.

Thousands of companies have begun offering work from home positions and many CEOs and executives foresee the trend continuing to grow. In fact, below we have interviewed 10 CEOs of companies of all sorts, and their experiences and tips on working remotely.

Are you thinking about making the change? If so, find out why these CEOs chose this work style and how they keep afloat.

  1. What motivated you to work remotely?

Karen Donoghue, Founder of Human Logic

I work remotely with my clients and they are located all over the world. My motivations for working remotely include being able to best utilize my time to help my clients solve their challenges, save time and reduce costs associated with travel    and to be able to work with a variety of leading-edge client projects spanning enterprise cybersecurity, healthcare robotics, and device management among others. It’s a huge benefit to not have to spend time commuting to and from an office, and to use that time to do productive work for clients.

 

Laura Spawn, CEO and Co-founder of Virtual Vocations

I turned to remote work as a solution for my family. At the time, I had three kids under the age of 5—a 4-year-old, a 2-year-old, and a 2-month-old—and my middle child had just been diagnosed with a disorder that would be requiring intense therapy. My husband also decided to go to medical school around that time, which meant we would be living out of the country for a little while. I wanted to return to work to provide a little extra income for my young family, but I had a lot going on and I didn’t want to cut too much into valuable time with my husband and kids, so I turned to telecommuting.

I quickly learned that finding remote work wasn’t as easy as it sounded—between vetting potential employers and looking for roles that matched my skill-set, I was spending upwards of 20 hours some weeks searching for remote work, and I knew there had to be a better way. That’s why I teamed up with my brother to create a website that would make searching for remote work safer and easier—and the rest is history.

Adriana Herrera, Founder and CEO of EpicHint

I started the EpicHint as a passion project while on sabbatical traveling around Mexico, surfing, and eating my weight in tacos. The project has grown into a high growth tech startup. I attribute part of the rapid growth to living as a Digital Nomad. I’ve done the “Silicon Valley/ Silicon Beach thing”. The areas are great for knowledge share and growth resources. They are also an echo chamber. Working remote means that I’m meeting people from around the world and from all walks of life. Varying perspectives on completely unrelated topics have lent insights to develop creative solutions which have in turn resulted in unprecedented growth.

 

Amad Ebrahimi, Founder and CEO of Merchant Maverick

There were a couple reasons why I chose to work remotely. The first and main reason was for efficiency. When I was working a 9-to-5 job I found it highly inefficient to have to sit in my car in traffic, especially where I live in Southern California, wasting time that could be used to be productive. The second reason is that remote work was beginning to be accepted by employers during that time (I remember reading about it in several books), and most of the sentiment within those books was that requiring employees to travel or commute to work is just plain inefficient. I then carried that mentality into my current role now as the Founder of Merchant Maverick and built a fully remote team as a result.

Michael Drake, President of PMG Home Loans

I find that working in a different location sometimes sparks new thoughts. I generally work remotely when working on strategy or long term planning. Also, it can help our team reduce their reliance on me. If am just up the hall, it is easy for staff to just poke their head in to ask a quick question instead of figuring it out on their own.

 

 

 

John Rampton, Founder and CEO of Calendar

A lot of things motivated me to work remotely. I have family here in Palo Alto, CA. I also have more connections and opportunity with the industry here as well. I have connections worldwide, but being right in the middle of CA with big cities surrounding me is a big benefit. My team is located in Palo Columbia, MO, Salt Lake City, UT, Pune, India, and many other locations.

 

 

 

Leo Friedman, CEO of iPromo

Working remote breaks up some of the monotony of the standard office setting. The freedom to get out of the office and continue to work is a major plus.

 

 

 

 

Jeff Root, Founder of Rootfin

Access to the best talent nationally. There was limited talent in our local area and everything we do is via email and on the phone, so it made sense.

 

 

 

 

Katharine Wolf, Founder and CEO of Odetta.ai

Quitting my job and working remotely has been liberating, terrifying and humbling. I had the entrepreneurial bug for many years until one day I got an idea that I just couldn’t stop thinking about. I had heard statistics about this massive pool of highly educated pool of female talent underemployed all across Asia and the Middle East. A bit daringly, I booked a flight to Pakistan, a place where the overeducation underemployment seemed most pronounced. It was during this trip, after meeting hundreds of women, that I decided to build from scratch a remote working platform designed for ambitious women centered around flexibility and community.

A little over a year ago, I embarked on this adventure leaving Brooklyn en route to the Middle East, settling in Amman, a city that soon became home. Following the heartbeat of the start-up, I moved from Amman to Paris, and ultimately to San Francisco, and this idea has become a team of nearly 150 women working from all parts of the globe. Our vision is to become the highest quality on-demand labor solution in data-related services, and the career platform of choice for women in the Middle East and South Asia.

Right now, Odetta is a community of 5,000 women from 15 different countries, serving clients including Google. Our community has members from Pakistan, UAE, Jordan, Egypt, Philippines, Tunisia, Morocco, Singapore, India, Turkey, Saudi Arabia, Sri Lanka.

  1. Benefits / Challenges to working remotely?

Sebastian Britz, CEO and Co-founder of Digitty.io

Location-independent working is a trend – not only for employees, but also for many companies.

Where new freedoms arise for the individual, completely new recruiting opportunities are offered for companies.

The remote work model also promises employees a permissive and self-determined way of working. Nevertheless, they can still benefit from all the advantages of a fixed employment contract. The majority of Freelancer have been more flexible in their working lives, which has led to more personal satisfaction and even to an increase in their sense of health. Freelancers get access to work from all over the world – Freelancer can work on projects for companies of all sizes and budgets throughout the world. No language or geographical barriers will hold them back.

Reduction of a previous location disadvantage. In particular, small and medium-sized enterprises located outside urban agglomerations are increasingly complaining of a shortage of skilled workers and declining numbers of applicants. Remote work almost looks like a recruiting miracle here.

 

Laura Spawn, CEO and Co-founder of Virtual Vocations

The biggest challenge for me over the years has been finding the right balance between my personal and professional lives. When we first started the company, I found myself working long hours, often late into the night, because I always felt like there was one more thing I could get done that would help grow the business—and since my office was at home, it was really easy to get sucked into work outside of office hours. The final straw for me was when I found my then-2-year-old screaming my name and shoving her hands under the door to the laundry room trying to get to me, while I was in there trying to take a business call. I knew I had to make a change.

 

Adriana Herrera, Founder and CEO of EpicHint

My previous companies each had an office with employees. I’d get in at 7:30/ 8 am to have at least an hour of quiet before others showed up and I’d stay an hour after everyone left to have additional quiet time to work. As the leader of the company I made sure I was always well presented (hair, makeup, great outfits). The benefits of working remote are not having to wake up early or stay late because there are established processes to facilitate communication and collaboration at set times. I of course had processes at my other startups but you can’t just ignore someone and tell them to go away which would result in my not being as productive daily. Working remotely I get 3x the amount done in half the time and do my best work in a bikini with no makeup on. There’s no way that would have happened with teams in an office.

The largest challenges to working remote is ensuring, strong wifi signal, access to power, and making sure to schedule meetings on the right time zones.

 

Amad Ebrahimi, Founder and CEO of Merchant Maverick

There are many benefits — I am able to avoid a commute, I am able to conserve my energy to be more productive, and I am free to dictate my schedule as I please. The challenges are, there are plenty of distractions to keep me from being productive, it is difficult to fully engage with the team on a personal level when you are remote, and of course the isolation is not always fun.

 

 

 

Michael Drake, President of PMG Home Loans

It is easy to get distracted when working remotely. You have to really be disciplined and keep distractions to a minimum if at all possible.

 

 

 

 

 

John Rampton, Founder and CEO of Calendar

There’s many benefits and challenges of working remotely. I would have to say the greatest benefit is we get to have company retreats at least once a year and travel. Maybe the biggest challenge is the time difference, and also not being able to meet in person all the time. Other than that, I love having a remote team.

 

 

 

Leo Friedman, CEO of iPromo

Answer to question one is a benefit. Other benefits include traveling and working, not being confined to the ‘9 to 5’ model. The biggest challenge is you can be easily distracted while working remote. It takes a certain discipline to be able to work remote. A challenge that is related to traveling and working is access to some sort of internet or limited technology type issues.

 

 

Jeff Root, Founder of Rootfin

A big benefit as a business owner is location arbitrage. For your admin work, you can find workers in places where the cost of living is low and they don’t require a big salary.

A big challenge is making employees feel a part of the company and not on an island at their home. Even with communication platform’s like Slack and weekly calls, some people have trouble feeling connected and it’s hard to figure out who those people will be.

 

Katharine Wolf, Founder and CEO of Odetta.ai

Working remotely is all about independence. I can design my own productive work environment, based on how I feel each day, and what is required in my life.

One of the major downsides that come from remote work paired with entrepreneurial journeys is isolation. I have combated that with our Odetta virtual community, and by joining entrepreneurship groups, running clubs and soccer teams.

  1. There can be a lot of distractions when working remotely. How do you stay motivated and focused?

Sebastian Britz, CEO and Co-Founder of Digitty.io

The secret of staying focused is very simple, you just need to be interested in what you are doing. If someone doesn’t really like his/her job, then working remotely can be challenging, I agree. But for me it’s not the case, cause I’m very passionate about my work.

 

 

 

Karen Donoghue, Founder of Human Logic

If I do need to meet with a client, I might fly in for a kickoff meeting or workshop presentation but I do the bulk of the work remotely. I do not have a problem with distractions while working remotely but when I first started doing it I had to really learn to focus – like any skill one improves with practice. I stay motivated by having a great standing desk setup, large monitors and excellent noise-cancelling headphones and after the work day is over I take a long walk to clear my mind.

 

 

Laura Spawn, CEO and Co-founder of Virtual Vocations

For me, staying focused and productive is a matter of working at the right times and in a meaningful way. I only have so many hours in the day to be a great mom and a great business owner, so I schedule my work time around when I’m most productive, and when I’m with my family, I make sure I’m unplugged and focused on them 100%. Having a separate, dedicated space for work at home helps with that immensely.

 

As far as self-motivation goes, I’m not afraid to celebrate even the small stuff. I like to spend the last 15 minutes or so of my workday completing as many “two-minutes-or-less” tasks as I can, like responding to emails or setting reminders to get back to my colleagues on Slack. Knocking out so many items on my to-do list at once gives me a sense of accomplishment that carries into the next day and helps me start the next morning ready to tackle the day ahead.

 

Adriana Herrera, Founder and CEO of EpicHint

I’ve always been pretty good about not getting distracted. On occasion what has kept me from working is not wanting to be seen working. In some locations outside of the US being wired into my MacBook identifies me as someone who may have money which could lead to being robbed. I have met lots of travelers and there is a type that will ask questions about the type of work I do while looking at my MacBook. I can’t read minds but my intuition has always given me red flags alerting to some form of danger. At that point I end up “distracted” because I leave and “hide out for a bit”.

 

Amad Ebrahimi, Founder and CEO of Merchant Maverick

I think the motivation comes intrinsically. I am pretty focused on my results and goals so that makes it easy for me to block out the distractions that might prevent me from being productive. Through the years the habit has been ingrained in me so now inertia has taken over and makes it almost automatic.

 

 

 

Michael Drake, President of PMG Home Loans

If motivation is an issue, then working remote is not for you! I do find that I need to have a quiet place with a door that I can close. If the door is closed, then my family knows not to bother me.

 

 

 

 

John Rampton, Founder and CEO of Calendar

You’re right; there are a lot of distractions with working remotely. I stay motivated and focused by scheduling everything out. This way, I don’t end up with random calls and unplanned meetings. I have a lot of things automated as well, and I delegate those tasks to my team members. I can stay more focused on the priorities and tasks at hand this way. I also take time to relax and refocus. I might take an occasional walk to get some fresh air or brainstorm ideas or solutions.

 

 

Leo Friedman, CEO of iPromo

Working remote is not for everyone. The distractions can be too much for some and their work will suffer. Start your day off by setting goals and writing them down. Having a set list will keep you focused on those tasks and will keep you from wondering. Have a daily plan and stick to it.

 

 

 

Jeff Root, Founder of Rootfin

Change locations often, even at home. Go from your desk to the kitchen table. Sit outside or on your couch. Work from a coffee shop or co-working space. A quick change of scenery re-focuses you.

 

 

 

Katharine Wolf, Founder and CEO of Odetta.ai

I think this is such a misconception.

Being at work or in a co-working space is SO MUCH MORE distracting than working remotely as there are literally hundreds of distractions. When you work remotely, you can design your ideal environment, whether that’s at a coffee shop, in your living room, or in your car.

You actually need a lot of discipline to turn off work at the end of each day.

  1. Where’s the weirdest place you’ve worked?

Sebastian Britz, CEO and Co-Founder of Digitty.io

On an island in Malaysia.

 

 

 

 

 

Karen Donoghue, Founder of Human Logic

The weirdest place I have worked remotely was in a tiny village high in the French Alps in the middle of winter. During an afternoon video conference call an avalanche struck wiping out power for the entire village – and all communication including cellular failed until the avalanche was cleared the next morning.

 

 

 

Adriana Herrera, Founder and CEO of EpicHint

I don’t think I’ve worked any where too weird. The weirdest has been on the side of the road while driving from one city to another. A client we were onboarding called and needed something urgently so I pulled off to the side of the road, turned on a hot spot, got them what they needed, and continued on.

 

 

 

Amad Ebrahimi, Founder and CEO of Merchant Maverick

Haha! That’s a tough one; probably on the side of the road in the desert on my way to Utah. I was on a road trip and I remember I received a really important email that I could not leave unresponded. I pulled over on the side of the road in an area that had semi-decent wifi and got to work. I think I stayed there for at least 3 or 4 hours.

 

 

 

Michael Drake, President of PMG Home Loans

I am fairly pedestrian. Just hotels, airports, home office, and the occasional Starbucks. I would probably be far too distracted if I went somewhere particularly weird.

 

 

 

 

John Rampton, Founder and CEO of Calendar

The weirdest place I’ve worked would probably be in my bed. In 2006, I was working at a construction site trying to pay for college when I was run over by a large skidster. It snapped my left leg in half and pretty much crushed my dreams of walking again. Over the next 12 months I was confined to only my bed being sponge-bathed. I had 3 surgeries and was told that I would never walk again. So, I had to learn how to still have an income and be productive while I was confined to my bed.

 

 

Jeff Root, Founder of Rootfin

I once hosted a live webinar from the side of the road in the middle of the desert on a road trip with my family. There was no wi-fi so I called in on my cell phone and had someone in my office manage the slides as I was presenting and using my smartphone to access the slides and the notes. It went well!

 

 

 

Katharine Wolf, Founder and CEO of Odetta.ai

I have lived in several different countries in the past year since starting my remote work experience. In Amman, there was a little deck near my house next to a guy who kept birds, and every few hours he would let them out. It was one of the most beautiful places I have ever worked. I dream of the sounds.

I also work in my car, all the time. Generally, I am hustling my way around San Francisco and that means driving to the folks who will meet me. It also means that I take calls in between meetings from my car. I like to drive to look-outs and parking spots with a view, like Chrissy Fields. I am often in Big Sur, working from the back of my car.

  1. Any advice for those who are transitioning to a remote work environment?

Karen Donoghue, Founder of Human Logic

During a project I intentionally stay in frequent contact with clients, keep the team abreast of progress and have frequent check in calls using conference calling systems such as Zoom. When one is working remotely it’s important for the team and your collaborators to know that you are active and available, so I think being very proactive in communicating helps to address challenges. For those transitioning to remote work, I suggest ensuring that you have excellent WiFi with a backup method (e.g. tethering through a mobile phone) in case your connectivity fails. It is also helpful to have a quiet area where you can speak without background noise so clients can hear you clearly.

 

Laura Spawn, CEO and Co-founder of Virtual Vocations

For me, the solution was developing a strict routine that allowed my kids to get the day-to-day structure they needed while ensuring that I met my expectations for myself both as a business owner and as a mom. Early on, this meant my kids had regular playdates and spent time with my husband and other relatives often while I was working. As my children have gotten older, I’ve set boundaries in other ways—I have a dedicated home office that helps me focus and feel “in the zone,” and I set my work hours around my children’s schedules and my own preferences; I do the bulk of my work in the mornings, when I’m most productive, and then log off when my kids get home from school in the afternoon. Over the years, setting aside separate time and space for work has helped me ensure that I’m not dropping the ball on my responsibilities—either as CEO or as a mom.

 

Adriana Herrera, Founder and CEO of EpicHint

I like to get things done as soon as they hit my list. This Type A trait, for better and worse, has helped me successfully build EpicHint remotely. Remote work takes thoughtfulness when it comes to working with teams and clients. If you are good at, or can hire someone good at, establishing process that support operational efficiency then do it. I would not recommend remote work to anyone that doesn’t thrive in autonomy, using processes, or on deadlines.

 

 

Amad Ebrahimi, Founder and CEO of Merchant Maverick

Do not isolate too much lest you wish to be plagued by depression. The best way to avoid over-isolation and cabin fever is to simply go to your local coffee shop, bookstore, coworking space to surround yourself with people even though you may not necessarily converse with them, it’s still good to have them around.

 

 

 

Michael Drake, President of PMG Home Loans

Get dressed every day just like you are going into the office. It might sound like it’s a bit much, but things like this help frame your mind to get to work. Create a daily ritual, and follow it.

 

 

 

 

John Rampton, Founder and CEO of Calendar

As for advice for those transitioning to a remote environment, I would say no matter where you are, always keep a calendar. I have a shared calendar with all of my remote team so I can see when they are available and when they aren’t. They are also time-zone specific, so when scheduling events I can see what time the event is on my end and their end. This way, you know their availability and capacity. It makes scheduling time with them so much easier!

 

 

Leo Friedman, CEO of iPromo

This builds on question 3 but setting a daily, weekly, and monthly plan helps keep focus while working remote. Stay consistent in your set up as well. Know exactly what you need to successfully work remote and make sure you always have it. Remote work will take time to get comfortable with. Find what works for you and stick to it.. Remote work is a great skill to have and can benefit both the employee and employer.

 

 

Jeff Root, Founder of Rootfin

Make sure to have your own dedicated workspace at home where you can shut the door. It can’t be your bedroom as those lines between work and rest will be blurred.

 

 

 

 

Katharine Wolf, Founder and CEO of Odetta.ai

Find a community of remote workers. It is surprising what a few virtual meetings can do to make you feel part of something larger. It’s incredible what a slack channel of emojis can do to lift your mood.

Know thyself. I know what I need to keep in the fridge to remain productive. I know that I cannot leave certain books out else I will get sidetracked.

Take advantage. I am more creative when I know I can drive somewhere beautiful, and think of some hard problem I want to solve while staring at the ocean. Sometimes a little perspective can do wonders, and I definitely take advantage of not having to sit in a conference room all day.

  1. Anything else you’d like to add?

Sebastian Britz, CEO and Co-Founder of Digitty.io

Costs can drop or at least be more flexible than if you had to rent offices and hire every employee full-time.

This way, the company can attract talents and specialists who see remote work as an opportunity to choose their own life center or who would otherwise not be able to move.

If necessary, it can be used to cover different time zones, regions of the world, languages and cultures, which can be particularly interesting for international companies.

Freelancer are more motivated to work on a particular project which they chose by themselves. As a consequence, this also results in better work results and high-quality products.

 

Adriana Herrera, Founder and CEO of EpicHint

Working remotely makes it feel like I can breathe. I push myself very hard with KPIs. No matter how hard I push myself I feel free. That was never the case in LA or SF. There is something about not going into an office that has made me better at what I do. Rather than be an entrepreneur that talks about creating and innovating I do it every day from the moment I wake up, to where I wire in, to the product and company I’ve built. Remote work breeds creativity.

 

 

Amad Ebrahimi, Founder and CEO of Merchant Maverick

Yes, I remember when I first started working remotely I felt guilty in some ways because I did not feel like I was being productive. It’s not that I wasn’t actually being productive it was that I wasn’t an environment where I would clock-in and clock-out (so to speak), and for some reason I felt this weird guilt. Understand that that guilt will be there in the beginning but remember that output and productivity are all that matter, not being in a specific location.

 

 

John Rampton, Founder and CEO of Calendar

If I could add anything else, it would be that no matter if you’re remote or local/in-office with your team, it’s always good to respect everyone’s time. Being remote not only allows, but tends to create, more scheduling and strategic planning. Being in-office, we tend to think there isn’t a big need for scheduling things because everyone is right there and can be met in-person. No matter what, you should always have a team calendar so you are aware of everyone’s time and capacity. This helps with being able to really keep everyone on the same page and know when everyone’s availability is. Everyone tends to be more focused and productive this way.

 

Jeff Root, Founder of Rootfin

Building a remote culture where everyone feels connected is key. Having shared goals as a company with rewards like gift cards for hitting monthly/quarterly goals goes a long way. Having annual meetups in exotic locations if you hit annual goals is a way to get everyone working as a team.

 

 

 

Katharine Wolf, Founder and CEO of Odetta.ai

The Future of Work will be Remote. I believe that the best talent will demand it, and the best companies will be those that figure out how to leverage talent from all parts of the global in a distributed manner.

 

 

 

 

Thanks you to all of our participants! If you’re interested in being part of a round-up focused on leadership, hiring or would like to submit a guest post, please email Kollin at [email protected]

Jamie

Jamie

Founder & Managing Director

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