Mike Stratton: Making efficiency happen and finding “shipwrecks”

August 6, 2018

Our latest interview with Mike, Senior Manager of IT at Hotel Tonight, everyone’s favorite hotel booking app. Mike was formerly IT Director @ Anova Culinary, IT Manager @ Square, Datacenter monkey @ Apple, Nortel Networks, Cisco.

What do you ACTUALLY do?

Aside from setting IT strategy from end-user support to ERP systems, my job is frequently about making efficiency happen, getting technology out of the way, discovering “shipwrecks” of the past and optimizing the overall IT environment.

What types of devices do you support?

I’ve worked at mostly Mac-only or Mac-mostly shops since Apple in 2003, and Square in 2011- there’s a smattering of windows for the Excel junkies in accounting, a few iPads, and a fleet of MacBook Pros.

What’s your favorite piece of tech?

While I couldn’t live without my iPhone, I think my favorite thing is my iPad Pro. It’s the best laptop/tablet/travel-sized photo editor I’ve ever had. I love it.

What tools or apps are most important to your job?

Slack, G Suite, and a web browser.

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

I’m happy to do both! Hands-on is more rewarding from the “get-your-hands-dirty” perspective, but troubleshooting from remote is a weird combination of being Mission Control for Apollo 13, and having to explain things in very simple but precise terms.

Favorite thing about your IT environment?

It’s basically all-cloud/SaaS, which is great!

Thing you’d most like to change about it?

I’m not the world’s biggest fan of Meraki.

What’s on your desk?

MacBook Pro, an Apple Cinema Display, quiet USB desk fan, and a bottle of whiskey.

How did you start your career in IT?

Well, I had this friend who ran some MOO servers (text based online games), and his wife worked at Cisco, and she got me an interview for a contractor position in datacenter operations back in ’99….

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

Externally- that because I worked in an Apple Datacenter, I must know how to fix iPhones. Internally, that IT should own re-ordering paper for printers. 😂

What was your proudest professional moment?

Two- completing the IT and A/V side of the massive Square HQ build at 1455 Market Street, and completing the full IT takeover of an acquired company in 7 hours, despite having had my Network Engineer quit the week prior and needing to do all the NetEng work myself.

What are the biggest challenges in your work?

Expectation setting.

Most cringeworthy request?

A team asking if we could build a web app to accomplish something, when all they needed to do was swap step 1 and step 2 of their workflow to make everything work in the process they were executing…

Do you stay hydrated at work?

Cold brew in the morning, plenty of SF tap water for the rest of the day.

CLI or GUI?

CLI.

DIY or turnkey?

There’s room in the world for both.

Where can people follow you online?

I’m on twitter.com/chiangku – be forewarned that I’m highly political, highly opinionated on technology, startups, economics, baseball, and extremely sarcastic. I do not recommend following me.

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