However my manager gets along managing me and 5 other employees, all remote, no problem. We have a weekly group call and an individual call every one or two weeks, and we supply a monthly email giving brief details what we did over the month (no more than 20 or 30 lines). The rest of the time we chat on IRC and by email as necessary. We meet together once or twice a year, usually combining that trip with some other event such as a conference to reduce the number of extra airfares.
Pro-tip: focus on hiring the right person for the right role, not just the best-person-you-can-find-but-you-don't-have-a-good-fit-spot-for-them, and outsource things that are not core competencies (perhaps SEO & marketing, perhaps UI/UX, perhaps even mobile dev). Use common sense and treat people respectfully. Make providing an enriching workplace and a good work/life balance part of your mission statement.
I'd never do that.
As it turns out, it's not that bad at all.
Having everyone working remote is actually a blessing - it means that all of our processes are optimized for an asynchronous workflow. We use a private IRC server for all internal communications, email for conversations that need to be a bit less ephemeral, a tracker for our various projects (Pivotal, in this case) that need attention, Dropbox for file transfers and wireframes/mockups, Google Docs for spreadsheet-y things, Google Hangouts and Skype for video/audio communication, and our organization Github timeline for all things code-related.
Additionally, we try to keep the management overhead to a minimum: Weekly company calls on Fridays where we discuss internal dev/design things that happened over the week and what movies we saw or what level our Diablo characters are at, and then project-specific calls as needed during the week. All but the all-hands call on Fridays are optional; if you don't have anything to say, then you just don't join the call. We also try to get together for a more face-to-face gathering once a quarter, and try to pick a fun and convenient city in the world to meet in.
It's not black magic. It just takes good people and some minimal async-focused processes for it to work. Hire bad people, stuff goes bad. Implement too many synchronous (read: obligatory meetings, calls, timesheets, status reports, etc.), and stuff goes bad.
As well as the video interview there is a summary of the points listed for easy reading / linking.
The site is on a .tv domain and I am pretty sure it began with an m. When / if I find it i will edit / reply to this comment. In the meantime if anyone can remind me what the name is...
EDIT: Found it, http://webpulp.tv/
My problem is with the word "I manage 40 people remotely". Almost no one can manage 40 people themselves, probably no one can do it well. It sounds instead that you "run a company of 40 people remotely through managing seven people remotely". I got seven from the department heads meeting you described.)
Of those seven people you directly manage, how many of them are in the same location of their direct reports? It sounds like you have an office manager in Orlando who manages a good sized group of people. What percentage of your employee's work in that office. Because if its a high percentage, then a large part of your true solution on how to manage 40 people remotely is to hire someone who manages them locally.
That's the way I think it could be read and that distracts greatly from the other interesting tools and processes you discussed.
Our VP Sales and Chief Product Officer manage all remote people.
I have a remote team and we're growing but I would like to stay that way for as long as we can so I'm interested in hearing about some of the specific issues.
So is the eventual goal to just have several different offices but no remote workers?
We'll just have a concentration in Portland and Orlando.
Completely off topic, but I always do a bit of a double take when I realize that from Florida, Portland is a lot farther away than, say Bogotá or Caracas. I guess you get used to looking at US maps without any context as a kid.
I'm just about to start a full-remote schedule at the job I've had for 7 years. I'm extremely nervous about my future with the company. I work for a big, older tech company where remote working is an afterthought, not ingrained in the culture like Treehouse.
We're moving from Massachusetts to Tampa, FL to pursue a job opportunity for my wife (She's an attorney). I am extremely lucky to have been approved by the corporate chain to continue my responsibilities remotely.
Who knows, if it doesn't work out with them, maybe a job at Treehouse is in my future!
Since I wrote that post I joined Mozilla as the only employee out of Scotland and I feel like I need to write the post again, Mozilla are superb at dealing with remote employees which I am sure comes from the foundations as an open source project.
This process has been on the forefront of my mind quite a bit lately, as I am growing my company, Canyon Oak Partners (SEO/PPC/Design/Dev) and a supporting SEO Audit software offering (its in private beta).
At this point, the most important facet I wish to grow is the sales team. My partners and I are discussing the need and pros/cons of getting an office, as we all work remote right now. We also gather at my home (I have a spare bedroom as my office and we set up around the rest of the place) a couple days a week.
Our thoughts lean toward the social energy an office brings, but I love not spending the money on an office.
Do you have any advice on managing a remote sales team?
On an interval you like, we send out an email to each team member reminding them to write a status update of what they've been working on. Everyone's status updates are gathered into a summary email sent out the next day.
We're in our free beta right now and would love some feedback. Give us a try at http://TeamSnippets.com
Git commits are way too technical for non-engineers and task trackers either have too much information (i.e debate on how to do X and Y) or too little information (i.e just a simple task title).
Don't do it yourself if it is not your focus, but don't outsource it. You need someone in-house who can not only manage the administrative paper works but also give you advices about what's best for your own company.
You're looking at 65 employees at $100 a month to make that pay off.
For most companies between 4 and 65 people, outsourcing HR is a big headache reducer. Having worked at companies with outsourced HR, I can tell you it's not amazing, and it could be way better. But HR is a cost of doing business, and not something you should be trying to do yourself as a young business.
NOTE: Not a strike against HR, just reflecting a reality that salary figures for HR people probably disproportionately understate their overall cost. HR people are much more unlikely to work at a company where the only compensation is salary.
Update: even if you do hire some flesh and blood to sit behind an HR title, they are still most likely going to outsource things like payroll. Companies like Paychex are huge because they make sense and save a lot of money.
Compared to SF, the cost of living is far more reasonable for experienced folks that have or want to start a family.
The area is attractive with a lot of natural beauty, mild weather, and lots to do.
SF is only a short plane ride away to meet with VCs and angels, and you're still in the same time zone as them.
The business climate seems better and the government is pretty amiable for new businesses.
The one thing it still lacks is diversity. Seattle and SF are still far better in this regard.
I would think saying "I want to live somewhere where everybody is different than me" is almost as bad as saying "I want to live somewhere where everybody is the same as me"