All in-depth articles about my Apple career:

• How I ended up at Apple (1999)
• AppleCare (1999-2000)
• Mail team (2000-2004)
• Aperture: Senior QA (2004-2005)
• Eye Candy QA (2005-2011)
• Flipboard interlude (2011-2013)
• Calendar and Contacts (2013-2015)
• SwiftUI (2015-2016)
• Watch Hardware (2016-2017)
• Eye Candy QA (2018-2019)
• Why I left Apple (2019)

As I mentioned in a previous post about how I ended up at Apple, it was when I was handed a copy of Mac OS X Server 1.0 to bring home in my first day of interviews that I decided I had to be a part of Apple.

AppleCare (1999-2000)

My first job at Apple was doing data analysis on what people were calling Apple Support about it. It was primarily was is now called “Classic” macOS, but included all of Apple’s software products. It sounds boring, but I loved it and it had a real impact. I was the first person in this position.

Prior to me, the way that Apple Corporate would find out about the most important issues customers were facing were through an informal mechanism. Call agents that saw the same issue many times were encouraged to tell their supervisors and this information would filter up the chain until the ones deemed important made it to Cupertino.

Despite being non-systematic, they realized that there were likely issues that were never raised by phone agents simply because they were trivial to fix. Maybe it was just “disable this extension and reboot” so it didn’t seem worthy of mention.

My job was to create a statistical sample of notes from support calls and read through a LOT of them, sometimes over a thousand a week. From that, I would try to put issues in buckets and determine which ones were generating the most calls.

I presented my data to a weekly meeting that was attended by customer support higher-ups as well as representatives from marketing and engineering. It was great to identify these HUGE issues that were overlooked and to take steps to fix them so customers didn’t need to call about them anymore.

Although I loved my job, I was disappointed that I would have to wait after Mac OS X shipped before I’d ever get to work on it. And Mac OS X Server was such a low volume product that I spent very little time on it.

The Big Meeting (2000)

Sometime in 2000, I got a call from a woman in Software Engineering. I no longer recall who it was, but looking back and based on process of elimination, I think it was either Kwok Lau or Christine O’Sullivan. I didn’t know who they were.

They had heard through the grapevine that I was doing this presentation on issues with the current macOS and they were part of the Mac OS X team. They wanted to have me come give my presentation to them. They wanted to learn about what people were struggling with so that it could be applied to Mac OS X.

I was thrilled! I never thought to ask who would be in the meeting and it’s probable that I wouldn’t have known who most of them were at the time. The ones I remember were:

• Kwok Lau – then the head of Software Engineering Operations
• Christine O’Sullivan – head of Software Integration
• Scott Forstall – then head of applications and frameworks, but eventually the Senior VP of iPhone software
• Bertrand Serlet – then head of Platform Technologies (aka the Mac OS X engineering team), eventually Senior VP of Software Engineering

I mostly name drop because in retrospect, I’m very glad I didn’t know who was going to be there as I would’ve been incredibly nervous!

I gave my presentation and got a heavy grilling afterwards about how I got my data. These people were hard-core.

I found out years later that after I left the room, Bertrand and Scott huddled briefly and said, paraphrased, “We should hire this guy”

Shortly after that I was contacted by someone in recruiting asking if I was interested in a job in Software Engineering. Hard question to answer given that I’d never in my life considered a job in software engineering! She pointed me to the job description.

It was for a job on the Mac team in the Mac OS X group. I was already excited at that point. I knew email backwards and forwards from previous jobs and I found it very interesting. And I could work on Mac OS X!