The Job I Never Thought I Wanted…
February 2023
Welcome to the very first entry of Seed the Way, a recently inspired newsletter where I share my adventures and explorations in software engineering leadership. My goal is to seed some nuggets of guidance about my past and present as a 3x VPE (Vice President of Engineering). I’ve been a VPE in early stage, mid-stage, late stage, IPO and even Private Equity, but not necessarily in that order.
I decided to write a newsletter for other VPEs, aspiring leaders in software engineering and even non-technical leaders in the C-Suite about being a VPE. Why might you ask? Well, there are a lot of great newsletters on Substack and other mediums, but none that focus on this topic of being a VPE in tech.
The Job I Never Thought I Wanted
I worked as a software engineer in professional services my first 3 years in tech. I eventually landed a job at a publicly-traded, enterprise software company, called Manugistics at the end of the dot com boom in 2001. It was there where I first learned about the role of the Vice President of Engineering.
I spent 3 years at that company learning, growing and from what I could tell grinding as hard as I could in an attempt to be a respected software engineer. It was in the Supply Chain, Logistics and Transportation space. The company has been bought and rebranded a few times since I left in 2003.
In consulting shops, they typically don’t have a VPE role. They might have an Office of the CTO or a Center of Excellence. In software companies, the VPE role is often the executive responsible for all of the engineers.
I say it was the job I never thought I wanted because it was a revolving door during my 3 years. I swear in 3 years there had to be 5 people who took the leadership helm. I remember one of them came from Enron right about the time it wasn’t cool to say you worked at Enron. Needless to say, he didn’t last that long.
My first impression was the job wasn’t long for the taking. The pressures were intense. The expectations were pretty unrealistic. The life expectancy of the role was less than 12 months.
My second impression was that the next tier of leaders were the ones who got things done. They had long tenures as leaders. They were well liked by their staff and by other teams/departments. I remember fondly saying, when the timing was right to move into leadership, maybe being out of the crosshairs was a safer and more enjoyable place to be.
More Than a Decade and Still Going
I promise to share many stories in this newsletter in the coming months about the time in my life when I became a first-time VPE. It was an adventure to say the least. The shelf life of the VPE role during my time at Blackboard was similar to Manugistics. It was a little longer than 12 months, but not by much.
I was given my first shot as a VPE a little over 8 years into my time at Blackboard. I had various director and senior director roles from the very beginning of my time there. I spent almost 2.5 years in the VPE role before I left. I could have stayed longer, but I had already exceeded my expectations and survived in the role as long as I did.
After Blackboard, I went on a nearly 7 year run as a VPE of a venture backed startup called Contrast Security. I joined the team as their first VPE in the early days of investment. The company was moving from seed to Series-A. We had 1 customer and a small staff of a half dozen engineers, the founders and the first CEO.
It was a glorious run of growth, experimentation and lessons learned. As I said above, I will share those stories in future newsletters when the topic and the timing is right. Eventually I left Contrast. It wasn’t necessarily on my terms. All I can say is the timing was right and I was ready to go.
Since late 2021, I’ve been with another venture backed software company called Tackle.io. All I can say is that I didn’t bring a playbook in this go around. I’ve been experimenting with different behaviors and leadership techniques from day 1.
I’m obliged to say that my views might not reflect the views of my current and past employers. I can only assume given I’ve spent over a decade at these 3 companies that I must have done or am doing things right. Hopefully, I can plant some ideas in your mind as you navigate your own adventures.
What To Expect In Future Editions
I’m going to feel my way through my first dozen or so editions. I likely won’t have many readers at first, hence it might take some time for feedback to make its way to me to influence specific topics.
My goal is to produce a weekly edition, focused on a singular topic or theme. Ideally, each episode will take less than 5 minutes to read and digest. I’ve been thinking about additional editions that are shorter and more relevant to events, stories or topics making the rounds in social media and other tech mediums.