It’s been just over a year ago that our company went all remote. What this means is that we gave up the centralized office and all work from our homes now. When I started my software company back in 1994, I was sharing an office suite with my best friend who was also starting his CPA firm. It was great to get out of the house and helped to feel like I still had a job. I had worked for the government and a large corporation since I’d graduated from college, so I was used to “going to work”.

Remote WorkingOver the years SherWare has gone from working at home to multiple offices. There was a 12 year stint that I had the office at home and all the employees came to the house office. We had built our house and built in an office suite in the basement with it’s own entrance. After several years of this I decided to move out into an office space in town again. We kept this office for three years until we went remote last year.

So far, the experience has been great and I don’t think we’ve missed a beat. Clients have no idea we’re working from home unless we tell them. In this age of information, especially for a software company, working remotely isn’t only possible, it’s becoming more of the standard.

What are the benefits? Here’s what we’ve found:

  • The commute is terrific.
  • Less interruptions.
  • More freedom for employees.
  • Greater quality of life.
  • Less overhead.
  • Less structure.
  • Easier to find and keep good employees.

It can’t be all good, right? Well, there are trade-offs. Here are some of the challenges we’ve encountered:

  • Those with children have more interruptions.
  • There’s less structure.
  • You have to have more self-discipline.
  • It’s hard to get away from work.
  • Less boundaries.
  • It’s lonely at times.
  • You have to do your own tech support.

All of these challenges can be handled and the benefits far out-weigh the challenges. Also, the freedom of working remotely means that you don’t have to work from home if there are too many distractions. There’s been times that I’ve worked from the closest coffee shop just to get a break from the home office.


Today’s technology makes it easier than ever to have a remote workforce. The transition has been almost seamless for us and our clients because of technology. Here’s some of the technology we use to make this possible.

Phone System

You need the ability to have a phone system that works just like your central phone system in the office. You need the phone to ring for everyone at the same time and the ability to transfer calls to each other. What we’ve found that works best is 8×8 We’re able to do all of the above as well as have a virtual operator that let’s callers choose between sales and support. We’ve set the ring groups for each of these to go to the employees handling each. One of the nice things too is that we’re able to keep our original phone number and no matter which extension or location we call from, the caller id the person we’ve called sees is our main number and company name.

Inter-company Communication

One of the drawbacks of working remotely is not being able to walk over to another co-worker’s desk to chat or ask a question. We’ve tried several chat programs and the one that we’ve found that works the best is Slack. Slack seems to be all the rage these days and for good reason. It’s easy to setup and use and it makes keeping in touch really easy. We’ve been using it for a couple of years now and really like it. It’s easy to have a group conversation or a direct conversation with someone. One of the nice features is that there are phone apps for it too. If you don’t answer within a couple of minutes a message will be sent to your mobile device. It makes it really easy to stay in touch and get quick answers.

UPDATE: Read this recent post about group chat by Jason Fried. He brings up some interesting points.


In our company, we need the ability for all employees to be able to create and send an invoice or receive a payment over the phone. They also need the ability to search for invoices and payments. We’ve used QuickBooks for our accounting since the beginning of the company so it was only natural for us to switch to QuickBooks online a few years ago. It gives us all of the above capabilities and more. There are other great options out there like Xero and FreshBooks but since all of our data was in QuickBooks, it made sense for us to stay with it.

File Server

When you’re all centralized in one office it’s easy to share files because you usually have a file server on the network that everyone has access to. When you go remote that’s no longer the case. What we’ve done is switched all of our shared files to Dropbox and Google Drive. We purchased the upgraded Dropbox that gives a terabyte of disk space. We all share the same login so that we don’t have to purchase a business account. This works really well. The only problem with Dropbox is when more than one person edits a file at the same time. You’ll end up with conflicted files that you’ll have to sort through. Another nice features is that each workstation can decide what shared folders they’ll sync. This means that everyone doesn’t have to have access to all folders if they don’t need it. For the files we tend to edit at the same time such as documents and spreadsheets we use Google Drive.


Working remotely definitely has it’s advantages. It’s given us a lot of freedom that a centralized office doesn’t offer. It makes it much easier to be present for family matters such as a sick child or parent. It also cuts down on “snow days” since there’s no commute. It makes the hours more flexible as well.

One of the best resources I’ve found on remote working is the book by Jason Fried: Remote. In the book he details all the benefits and gotchas that, at the time, 37 Signals had encountered by working remotely.

How many of you work remotely? What’s been your experience?