Jun 11



I recently asked what you’d like me to cover here on the blog. I got a great question from @tfav

I’ve been running Treehouse since August 2010 from my home in the United Kingdom. We started with just three people (me, Nick Pettit and Jim Hoskins) and now we’re about to hit 40 full-time employees. I’m in the UK with one other person on the Support Team, our main office is in Orlando and the rest of the Team is spread out all around the States.

I’ve managed the company for almost two years from another country with up to an eight hour time difference. We’re doing $3,000,000+ in revenue with over 11,000 paying customers and growing fast, so we must be doing something right.

Here’s how I manage the Team …

Outsource HR

We use TriNet to do all of our HR (payroll, insurance, employment taxes and pension contributions). If I had to administer this, there’s no way I could’ve scaled the Team remotely this quickly or effectively.

Don’t do your HR in-house. There are a ton of legal requirements and logistical details to make sure you take care of your Team properly and it’s a huge time suck. TriNet costs roughly $100 per person, per month and it’s worth every penny. The UX on their web portal is terrible, but it’s very powerful and has all the functionality you need.

Hire a Financial Controller / Office Manager

We hired Rich Pettit (who happens to be Nick’s Dad!) as our Financial Controller and Office Manager. I sit 4,247 miles from our office in Orlando, and there’s no way I could run the company without a reliable and hardworking Team Member looking after the day-to-day operations. 

A lot of you will think you can’t afford this person early on, and you’d be right. Don’t hire this person until you are comfortable from a cash-flow perspective. But as soon as you can, hire this person. I think Mark Suster is really smart (which is why I invited him to invest in Treehouse and thankfully he did) and he agrees.

Use Campfire for company chat

When you’re separated physically you need a place to hang out and talk about random stuff or ideas. We use Campfire and it works great. We have a bunch of different rooms setup like:

  • Chiggity Chillin (company wide hangout)
  • Product Team
  • Dev Team
  • Firehose (commits to the Treehouse GitHub repo and deploys to Production)
  • etc

We use hubot to add stupid functionality to Campfire like this: 

Try out different modes of communication

We’re trying out a private WordPress install with the P2 theme to help the Product Team communicate more effectively. The Team was finding that the transient nature of Campfire was bad for having more meaningful long-term discussions about Product.

So far it’s working well and we’ll probably stick with it.

Use Go to Meeting + Google Docs

Whenever we need to meet, we use Go to Meeting. We tried doing multi-person meetings with Skype and it wasn’t reliable enough. GTM has been a great solution and it was affordable ($49/mo). It doubles as a great conference-call solution for meetings with outside people as well.

We use live editing in Google Docs (especially Google Drawing) to act as a virtual white board during our meetings.

I have a Leadership team that consists of seven people who I meet with every Monday. They lead the areas of the business like Video, Teaching, Product, Sales, Support, Marketing and Finance. We do this meeting on Go to Meeting and it lasts about an hour. Each person goes through what they’re working on so everyone is on the same page. As soon as I built out our Management Team I realized we needed these meetings to keep everyone informed. I knew what everyone was doing, but they weren’t coordinating with each other.

Before we created a management team, I met with everyone in the company every week over GTM or Skype. Once we started scaling the team, this wasn’t possible. 

The brutal truth is that meeting over GTM or Skype just isn’t the same as meeting in person. It’s OK but it doesn’t have the fidelity of meeting face-to-face. This is why we fly everyone into Orlando four times a year for 4-day company-wide meeting. These quarterly sessions really bond the team together and help makeup lost time for working remotely. They’re intense but fun.

Organize visually

We’re now using Trello for all our company projects. We switched from Asana because Trello is more visual and it’s a little easier to see how things are progressing. They’re both great tools - we just found the left-to-right kanban-style layout of Trello very easy to parse quickly. Each card is an atomic todo and you can see it moving through various stages to completion. Above is a screenshot of our actual “Product Team: In Progress” Trello board.

Give up?

Now that we’re up to 40 people and things are going 110mph with Treehouse, I’ve decided it’s no longer viable to manage the team from another country. We’re still going to operate remotely as a company with everyone spread out around the US, but as the CEO I really need to be on US time. 

So I’m moving my family to Portland Oregon where we’re going to setup another office for Treehouse. A lot of the team will still be remote but being closer will really help. My goal is to slowly gather Team Members in our Portland office but leave our Video Production and Teaching in Orlando (it’s affordable there and the office is established, so no need to move it). Alan, my Chief Product Officer, is moving his family to Portland as well so we can work together daily.

If you manage a team remotely, please chime in and share your tips in the comments.

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    Kingdom…. Perfectly timed insight...operate remotely- starting next month, Alumni...
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