Web Operations at a startup, the first 30 days…

Hitting the ground running

I’d recently found myself working at a startup fulfilling their needs for Web Operations. I thought I’d document and give advice for anyone else in the same situation.

Most howtos give you advice for the first 100 days. By most conventional wisdom, you need 90 days to really figure out what’s going on in an organization. Most medium and large organizations let you do this at a relatively leisurely pace. Being at a startup where things are changing at a blistering place, it’s easy to get turned around.

Make Lists, get it out of your head

You’ll find new information daily. Information about things you’ll need to know. Information about things you don’t. You won’t really know what’s what at this point. What you will want to do is centralize it in a place like Evernote. I’m not saying use a notepad, but you’ll want to make it searchable because by the end of a month you’ll probably have forgotten much of what you wrote down at first.

I found that I had so much to think about it was actually keeping me up at night. Take a page from David Allen, and write this stuff down. Honestly, I made a list called “All The Things” since we didn’t even have a ticket tracking system at the time and wrote down, literally, all the things people wanted, or expected to get done that fell under my purview. You’ll get better sleep knowing you don’t have to hold anything in your head.

It won’t be enough to make a list of All The Things. You’ll want to prioritize them as well. You may want assistance from your manager on some of these. Try and figure out what you’ll do in 2 weeks, 4 weeks, etc. Don’t try and put too much on your plate, don’t change the world in a day. You’ll want to focus on quick wins when you can just to get some early recognition.


You’ve probably done this at your former position, don’t neglect it now. Figure how how your boss wants status weekly, and take this opportunity to do weekly one on ones with your directs. The longer you wait the less likely you’ll do it. Get good habits in place as soon as you can. It’s a new job. Make new habits!

Of course, also identify your peers and talk to them whenever possible. It’ll be easy in the future to have adverse relationships with them since their goals may not align with yours. However, they’ll also be most important allies in helping you and the company achieve goals.

Gather Subject Matter

What do you need to focus on. What’s lacking in the company. Do they need better documentation, monitoring, uptime, is there a ton of legacy stuff needing upgrading, are there too many requests being jammed through the hopper, all the above?

You’ll want to gather tasks and group them together so you can focus on like tasks at once. See the First Hundred Days Reference below, and don’t forget the Limoncelli test.

You’ll also want to document everything you find, especially if its lacking. Otherwise, read read read about everything that works there, and definitely use time in your one on ones to find any other bugs under the rug.

The First Hundred Days