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Doug Roberts: Process escalation and prioritization

An interview with Doug Roberts, Senior Manager, Global IT Help Desk at OpenTable.

What do you ACTUALLY do?

I manage the Help Desk in our San Francisco, London, and two Denver offices. I plow the road for my team so they can get their jobs done, advocate for them and our end users when new processes or technologies are being considered. I’m a technical and process escalation point, and I manage and prioritize the plethora of projects we have outside of user tickets.

What types of devices do you support?

Mac and Windows laptops, Chromeboxes, video conferencing equipment, and iPads. There is also a small assortment of miscellaneous hardware — 3D printers, Raspberry Pis, and the like.

What’s your favorite piece of tech?

I have a place in my heart for the Flic button. I’ve used it to build Panic Buttons that sound alarms at our main help desk when a user runs into an issue with A/V in one of the large conference rooms – the button fires an automation that sends a Slack alert, opens a Zendesk ticket, and plays the Star Trek “Red Alert” sound at help desk.

What tools or apps are most important to your job?

Vagrant, Sublime Text, Zendesk, Jira, and noise canceling headphones.

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

Hands-on, hands down.

Favorite thing about your IT environment?

The teams. Our engineering, security, workplace, HR, and help desk teams are some of the best people I’ve ever worked with. OpenTable is 20 years old, so there is a lot of legacy technology and process to navigate — without the close cooperation of these teams, it would be impossible.

Thing you’d most like to change about it?

Like everyone else I’ve spoken to, I’d like to improve automation and get away from manually processing things like on- and off-board steps. See the previous reference to legacy technology.

What’s on your desk?

A prototype conference room doorbell (another Flic project), Groot, Mjolnir, Pickle Rick, and a parking ticket I need to pay.

How did you start your career in IT?

I got a job in college in the electronic imaging lab and found I was a lot more interested in the computers than the photography. I was luckily recruited by EFI in San Mateo for an engineering catch-all role that gave me a lot of exposure to different technologies. From there, I got hired as a “Glue Guy” at a San Mateo startup (founded by Thomas Dolby) to run the IT department. I was employee number 16 and helped them manage two growth spurts before we were a victim of the dot.bomb. I left California shortly thereafter, worked for big corporations in Ohio for a few years, and couldn’t get back to San Francisco fast enough.

What are the biggest misconceptions of your role, internally or externally?

Because Help Desk is responsible for enforcing processes from a number of other departments, people often think we’re responsible for them.

What was your proudest professional moment?

We had done a migration from on-site Exchange to Gmail and I’d been tasked with communicating the process to the entire company over the course of the 3-month project. The email communications were… unorthodox, as I tried everything to make them fun and interesting to read so people would, you know, read them. A few days after we launched, the company vice-president called me down to help configure his iPad for Gmail and as I was setting it up, he said: “Great job on this project – I’m glad we gave you a chance to be creative. I don’t usually read emails from the IT department, but I read every one you sent.”

I walked away from that interaction feeling pretty good even though it was clearly a lie: several of those emails were about how to configure iPads for Gmail.

What are the biggest challenges in your work?

The biggest challenge is trying to find time to do it right instead of doing it fast. Help Desk — especially understaffed as we currently are (we’re hiring in Denver and London!) — ends up being a field hospital where we patch ’em up and push ’em out. I’d like to staff up a bit so we can automate away the pain of tedious tickets. Related to that is trying to find time to write better code than I do — I hack together solutions to get the job done but often don’t have time to go back and improve them.

Do you stay hydrated at work?

Coffee is mostly water, isn’t it? So yeah: very hydrated and very jumpy.


A little from column A, a little from column B. I’m never without a command line window open.

DIY or turnkey?

I lean toward turnkey because we don’t have resources to do a lot of DIY work. That being said, when turnkey fails we roll up our sleeves and do it ourselves.

Where can people follow you online?

I tweet sarcastically from my unfortunately non-ironically named @OldGuyAtStartup account.

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