Dan Jacobson: Managing 700 employees with zero physical servers

A deep dive with Dan, Director of IT at Datadog.

What do you ACTUALLY do?

I support my team that takes care of the rest of Datadog. IT is responsible for identity and access management, corporate communication tools, office networks, end user hardware, IT security as well as onboarding all the new “Datapups”.

What types of devices do you support?

Lots of Apple things and some Meraki things.

What’s your favorite piece of tech?

Our new IT accessory vending machine! It frees up my team to work on other tasks and enables employees to get what they need 24/7. No ticket required!

What tools or apps are most important to your job?

My iPhone, Chrome and Zoom. Almost all of my job can be accomplished with these three.

Do you prefer hands-on, or troubleshooting from afar?

We run a BeyondCorp style network, so I have few things to actually get my hands-on. This is good since I still have PTSD from my days of patching and rebooting Windows servers from home at night and watching a ping to see when/if the server comes back up.

Favorite thing about your IT environment?

700 employees across the globe and zero physical servers! Also, no Active Directory!

Thing you’d most like to change about it?

Dealing with an almost exclusively SaaS environment, when G Suite or Slack is having issues there is little to do except refresh their status page. I won’t say I yearn for the days of restarting Exchange services but sometimes it’s nice to have some control.

What’s on your desk?

Varidesk Standing Desk, Apple Magic Keyboard and Mouse, Dr. Bronner’s Lavender Organic Hand Sanitizer, a Rain Laptop Stand and my trusty Klean Kanteen water bottle.

What was your proudest professional moment?

I used to work at a cloud backup startup where I built and implemented a cloud disaster recovery solution. When Superstorm Sandy hit NYC we had to actually use it for real for the first time. We failed over our own infrastructure as well as that of a few clients which allowed our businesses to continue to operate even though half of Manhattan had no power.

Most cringeworthy request?

Many years ago when I was doing IT consulting I was sent across town in a snowstorm to press the power button on the computer of a very rich and powerful person who was unable to push it themself. I stopped consulting shortly after.

Do you stay hydrated at work?

Straight H2O and when I’m feeling adventurous I reach for a Lime Perrier®


Depends on what I’m doing but it’s hard to be successful in IT without being comfortable with both.

DIY or turnkey?

Turnkey is good but it can usually only get you so far, especially in a SaaS environment. Being able to build and customize what you need is super important.

Who would you love to see interviewed here?

Rishi Dhar from Yext.

Where can people follow you online?

You can find me on LinkedIn and MacAdmins Slack.

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