Career in Tech

Reflecting On Four Years At Google

I recently resigned from my role at Google after four years (technically 20 days short of that) and so I wanted to take a moment to pause reflect on my time there. You can see previous updates for my 3rd year, 2nd year, 1st year and upon deciding to join.

To start, I should be clear, that I’m >50% sure that I’ll work for Google again at some point in my career and I currently have a 7.5% chance assigned to me being the CEO at some point. Google is a great company and has many productive years ahead of it. My leaving Google is less about me leaving and more about me being lured away. I wasn’t looking to leave (in fact, I was setup for another few years of fast-paced growth) but a company reached out and made me an offer I wasn’t able to turn down (more on that in a later blog post).

At some point I might take time to write more about Google, how it is changing and what I would do as CEO, but this isn’t the blog post for that. This is the blog post where I reflect on my decision to join Google four years ago and thank my lucky stars that I made that decision. (Scroll through my blog more to see other blog posts where I bemoan bad decisions I’ve made…)

Were The Reasons I Joined Google Good Ones?

Four years ago, when I joined Google, I wrote about why I decided to do so and I challenged myself to make sure I continually reflected on those reasons. Here I’ll look back on each of those to see if my predicted value was accurate.

Life never goes quite how we expect it will and often our forecasts are overly optimistic, so I’m interested to see which of these turned out about as I expected, better than I expected or worse than I expected. In the end I’ll determine if my reasons for joining were good ones and if those worked out for me (hint: they did).

1. The Google Halo

There is a saying from a Frank Sinatra song about New York where he says “If I can make it there, I’ll make it anywhere”. I feel like that is sums up my feelings on the Google halo after having worked there for a while.

Most people know Google to be a strong company, that hires strong individuals and so when they find out you got hired by Google, they figure you’re either good at your role, or at least good at making people think you are. After four years, a few big launches and multiple promotions, they eventually resign to the fact, that you might actually be good at your job.

Many people are more familiar with what Google is actually like these days (a lot bigger and more bureaucratic than the company that built a search engine 20 years ago) are equally impressed when they find out how much you were able to get done. They figure that with a more nimble company and a few similarly-skilled engineers, you might be able to get even more done somewhere else.

When I decided to join Google I said “That halo is beneficial for me as it allows me to associate myself with that perception which will likely create residual benefit for the rest of my career.” I find this to be true. I get a lot more inbound inquiries from recruiters than I ever had before. I’m being asked to discuss VP of Product roles at startups or Director+ roles at other companies where they wouldn’t have even returned my email five to ten years ago. In fact, my new job came about because the Chief Product Officer of one of tech’s hottest companies reached out to me, which was ironic, because they were on my short list of companies to check out eventually.

All in all, having a successful four years at Google has, as far as I can tell, permanently bolted that Google halo to my head. One bit that was interesting is that when I announced I was leaving, many of my coworkers were very shocked. More so than I would have expected. I think I got to the point where I seemed so much embedded in the Google culture that they could easily picture me staying for 10 to 20 years (as many Googlers have). I am going to take that for what it is, a compliment that even among Googlers, I stood as a bit of an exemplar of the company values. (TODO: More thinking about the weight of that to come in a later blog post about leading teams)

Result: As expected

2. The People

I took a bet on a team that had a few people I thought I could learn from and that proved very true. A number of very talented and kind individuals spent a lot of time with me over the past four years helping me figure out how to solve problems, and I was exposed to a lot of good ideas during that process (all of which I’ve stored away as strategies for future use). I’ve also made a few friends and mentors that I’ll stay in contact with for a long time.

As expected, people movement means that my former teammates at Google are now spread out to all corners of tech – many still in Google Cloud but others working in Core, Devices and Hardware or at companies like Stripe, Snowflake, Netflix, etc.

I had made a statement when I joined Google that “the people I work with now might end up being people I work with directly again later” which ended up proving true, very quickly. My new job will put me in close contact with a number of people I worked with while at Google and a number of people that previously worked with others I had worked with. In many ways it feels like the tech industry has currents of people moving around from company to company in various directions and I feel like I’ve successfully gotten myself into the Gulf Stream that is heading to the right places at the right time. (I guess we’ll find out if that is true in four more years)

The one part I haven’t yet taken advantage of is the Xoogler network. Perhaps now that I am post-Google I will end up connecting with them more, but to date that really hasn’t been a factor for me.

Result: Better than expected

3. Believe In The Company Mission

One of the reasons I picked Google over other tech companies is I believed in the mission. To build a sustainable company, you must benefit all stakeholders without harming any. Companies that do harm to a stakeholder eventually face the consequences of that (see: ITT Tech, Cigarette companies, Facebook, etc.). Google remained a viable business during the years I was there and I believe it will for a long time to come (and I back that statement up by holding onto stock I earned along the way).

There were some times I was extremely proud to be a part of Google. When COVID-19 hit, Google did a lot to help provide information that saved lives. When the economy stumbled as lockdowns hurt local businesses, Google helped folks gain new job skills. When Russia attacked Ukraine, Google was there to help keep people safe on the ground. When I did a fundraiser for Myalgic Encephalomyelitis, Googlers donated over $5k and then Google (the company) matched that. I’m glad that my hard work was resulting in profits that were, in part, going to good use.

Result: As expected

4. Flexibility To Change Projects Without Changing Anything Else

In the end I never used this feature, but it was nice to be able to have it. I wasn’t sure I would be able to spend four years on a team like Billing, but I turned out to be very wrong about that. (In fact, I’ll be doing even more of that in my next role).

I did find this to make management very interesting at Google. There are pros and cons to the potential movement and how that impacts managers. On one hand, it makes it easier to recruit because it is a benefit that can convince people to take a chance on your team. On the other hand, it could mean the folks you’re managing leave for another team, because that process is so easy. This ends up making a manager’s job at Google really hard, because they can’t just use salary and inertia to keep employees, they have to actually keep them engaged. But, as a whole, I think this is great for Google because it means most people have good managers and bad managers will tend to be revealed (and then either given a chance to improve or be asked to do something else).

Result: Less than expected

5. Personal Financial Considerations

This ended up delivering WAY beyond expectations for a few reasons.

1) Thanks to the liquidity of Google Stock (as compared to illiquid pre-IPO stock or that of a private company) I was able to buy a house for my family. At the time, that was one of the biggest financial items on our near term horizon – not the least of because Seattle is one of the most expensive cities in the world and a down payment for a house here can cost more than a house in many parts of the country. Deciding to join Google directly led to us being able to move into a home we own and bring a bit more stability to our lives.

2) Google’s stock ended up being worth much more than I had estimated. To demonstrate this I wanted to share an image from our compensation tool. I’ve hidden the exact amounts, but what you can see is my earnings per year with salary in blue, bonus in green and stock in yellow. The chart shows that while my salary went up a little bit each year (thanks to raises and promotions) the big jump was in the value of the stock I received. Not only did the price triple during that time, but I received refresh grants every year. So years three and four payed more than double what I got in my first year.

This stock increase wasn’t true of every company. While the whole market had some ups and downs, for the most part, Google tracked better than any other company I had talked to in 2018.


When I joined Google I wrote “My impression is the sky is the limit at Google and that high achievers are rewarded handsomely and disproportionately compared to average performers”. I believe this to be largely true at Google, though I think it is now also true at a few other companies. Along with the raises and stock refreshes I got (see the chart two above) I also got bonuses from managers and peers. Google has a cool perk called the ‘peer bonus’ where any employee can give any other employee a $175 bonus (there is a limit per quarter) as a thank you for going above and beyond their job. I got 49 of those in my 4 years at Google. I also got a number of spot bonuses, which are similar, but come from managers and are usually a bit bigger. From conversations and information people shared with me, I can confirm that while $100M per year is an outlier earning amount, there are plenty of Googlers who earn more than $1M per year – not even just executives, but some individual contributor engineers or folks managing small teams. Those numbers were mind blowing to me when I first heard them, but it confirms that Google is really a place where high performers can be compensated very well.

Result: Better than expected

6. Seattle Campus Size

Two+ years of my four at Google were spent working remote, so the Seattle campus wasn’t as important as I had initially thought it was. When I was in the office, I loved it though. A few thousand people is a big enough campus where a perk-heavy company can invest in perks like a gym, shuttle busses, baristas, etc. But it is small enough it actually feels a bit cozy instead of a sprawling anonymous city.

I got to visit 10 Google offices during my tenure and can confirm that something in the 1-4k range is a great size campus for the kind of atmosphere I like to work in.

Result: Less than expected (due to COVID WHF for 2+ years)

7. Ability To Gain Knowledge About Specific Topics

When I joined Google I had specifically named four things I wanted to learn about; cloud infrastructure, how to run a software company, if I liked working for big companies, and other cool technology stuff. All of those proved true. I learned a ton while I was at Google. I learned abut the Cloud, billing, how Google does things (the good and the bad), I got a lot more people management and team leadership experience and I got to spend time honing my executive presentation skills.

The part that surprised me the most was how much I enjoyed working at a company as large as Google. I don’t really like to blend in, or follow rules, or go with the flow. I like to stand out a bit, which I figured would be hard at a place like Google where a) there are 200k+ people and b) many of those people have done things like invent the internet, go to the Olympics, set world records, created Gmail, etc. It turns out I found my niche as the super friendly cloud billing guy that walked on a treadmill while I worked and made lame jokes on the company meme site. It was nice to find out that even at a big company, I could let my personality out a bit.

One other thing I want to highlight that is great about Google is that generally the company philosophy remains to hire smart people and put them in places where they will learn a lot. I love that style of work (as opposed to the style where you learn everything and then just keep doing the same thing until you retire). There were definitely peaks and troughs in my pace of learning, but in the low times, my managers and their managers were willing to have a conversation about how we could change my role to keep challenging me. That is really important for me, because if I get bored or feel stagnant, I grind to a halt. I love that Google is still willing to work that way for people who are seeking it and I’d encourage anyone who goes to Google to keep that in mind and always ask for it.

Result: Less than expected


All in all, joining Google in 2018 was an amazing decision. I learned a lot, I achieved a lot, I earned a good living, and my contact list is filled with new names of folks I’ll stay in touch with for a long time. If every decision went this well, life would be a lot easier.

I’d say that on average the specific reasons I joined delivered about as much value as I could have expected in the time I was there (which was about average for what I would have predicted). A few things turned out to be less valuable than I had expected, but a few turned out to be more valuable. This is some of why it is important never to make a decision based hopes for a single factor going well, especially if that is a long-shot item. I made a relatively risk-free decision with lots of potential upside and very little potential downside, and it ended up turning out about as expected – amazing.