Part 5 brings the series to a close. I’ll share what I’ve learned since my startup was acquired by American Express — adapting to a bigger company and a broader role.

Being Acquired

So after just over 7 years working for a startup, we were acquired in 2020 by American Express, where I work today. It’s been an interesting transition, good in many ways, bumpy in others, but it has presented me with many new opportunities and challenges.

Making Connections

When I first started at Kabbage (the startup I worked for), I learned who everyone was and what they did within a few weeks. There was only about 60 people there, so it wasn’t all that difficult. The department in the tech organization I work in at Amex is almost 15 times that size. Navigating an organization this size is easier when you have friends you can reach out to who are spread throughout. Connections might be more obviously important here, but I’ve learned that they can be crucial for many other things as well. I’ve worked with several people for over a decade now, and have many others whom I keep in touch with that I’ve worked with in the past. You never know when that person you used to sit next to will be a lifesaver for some odd reason. I say this mostly to point out that you should try and build a network, and when you do leave a company or organization, don’t do so in a way that burns bridges.

Delegation

At Kabbage I was a hands-on-keyboard individual contributor for the vast majority of my time there. I had a few roles where I led a small team (and mostly hated it), but mostly I was working on building things. At Amex my role has shifted more and more to being either a direct or in most cases indirect leader for others. It took me a long time to get comfortable delegating tasks to others, but I’ve come to realize that I can multiply my output by helping others do most of the work. There were two things I had to overcome to get good at delegating. The first was getting used to a more indirect dopamine hit when work was done. It’s often more satisfying to say “I did that”, but I had to learn that I can get a similar sense of accomplishment from saying “I enabled that”. The other was just getting comfortable with being “the boss”. It was initially very weird for me, but with the help of a career coach I was able to work through what I now realize was mostly just insecurity. (Side note: a career coach can be a great thing for anyone at any level of their career, I highly recommend it!)

Mentoring - Go To Them

A large part of my role at this point is essentially mentoring my organization’s engineers. I’ve struggled a bit with how to do this at scale with so many engineers in many different locations. One of the first things I tried was just letting people know I was always open for a chat if they were interested. I would make a similar offer to have in person one on ones when I would travel to other offices. What I found is that I was rarely taken up on these offers. Some of this is I think just the nature of having a more hierarchical structure, as it leads to people being intimidated, or thinking that they would be wasting my time. I do my best to keep myself approachable and reassure folks that talking with them is often the best use of my time, but I’ve found it to be much more effective for me to go to others instead of hoping they come to me. Sometimes this is in group formats like roundtables and sometimes I might ask my peers who on their teams would benefit the most from chatting with me. I’ve found that this approach not only gets people to talk with me, but also to build longer term relationships because I have already knocked down some of the barriers for people. It can be hard as you step into a higher level role to find time for things like this, but I think it’s super important.

Wrap up

This post wraps up my high level IC series. I hope others will find this at least somewhat informative. I’ve had an interesting journey with some amazing experiences. I consider myself very lucky to have had all the opportunities I have and I’m glad I’ve been able to seize at least some of them.