VP of Engineering: The first 100 days

“Welcome to BigCommerce”

I started the next stage of my career journey as VP of Software Engineering here at BigCommerce this past August. My first hundred days have been quite the wild ride – crazier and more fun than I could have imagined. I recently took a moment to reflect on how I got here and what the experience has been like. Here is my story:

First, Make an Introduction

It was important for the people here to know who I am, where I came from both an overview of my work background as well as some fun personal facts, likes, and hobbies that are part of who I am. For me that is among other things: family – raising my 3 young kids through the trials and tribulations of elementary school with my amazing wife of 13 years, tennis – I played in college back in my glory days and now keep my juices flowing by playing competitive league tennis, Bruce Springsteen – been to every tour in the past 20 years, and the Oakland A’s – for those outside of the U.S. that is the local baseball team.

First Impressions

First the good stuff. Engineers here are PASSIONATE. Engineers here have STRONG opinions on what needs to change to unlock the next level of performance and execution. Engineers here are NOT afraid to ask the new guy the tough questions. I love it! Partnering across three engineering hubs is hard but we are getting better at it. Product and Engineering executive leaders are both very well aligned and open to new ideas and ways of doing things, which is not always the case. And finally at the top, I have never met a CEO more direct and candid than Brent, which I learned very quickly in week two. This was very refreshing.

Next were some things that were either question marks or things that I clearly wanted to help impact. We have a decentralized technical decision making process that is very different than what I am used to. This seems to be working at times but at other times causing quite a bit of pain. Finally, all of our managers, directors, and execs in engineering are men.

So much to do. Where do we start?

The biggest mistake I made the last time I sat in this seat was that I didn’t want to make major changes in the early going because I felt that the team was working well together. I didn’t want to risk upsetting the dynamic before I established myself and gained their trust. Bad idea. You are put in a leadership role because someone trusts your judgement. If you see something that you feel is a priority to change, work with the right people to come up with a plan, roll the plan out, and then gather feedback and iterate along the way.  And if it doesn’t work, kill it and own the end result. Better to err on the side of action and iterate until you reach a successful place than hesitation and extended pontification. Lesson learned and I made a promise to myself I would not make that mistake again.

My role is very interesting in the sense that while there are some things that have to be done, most of what I do on the day to day is self-directed. This means that while there are 100 things on my list to get done at any given time, it is on me to figure out which to go after in which order and which will make the biggest impact.

I have always been good at prioritizing. Earning a CS degree while playing a varsity sport in college while also trying to have a reasonable social life is a bit of a forcing function for that. Then I got really good when I had kids. My wife works full time so we pretty much share the parenting duties. No longer can I put in regular large chunks of extra hours to get ahead. There aren’t enough hours in the day and there is a negative ROI for me after more than one bad night of sleep in a row.

So, how to figure out what to do?

First talk to everyone. Take it all in. How do you get people to open up?

Get out of the building. Buy people coffee, lunch, or walk around the block to create a relaxed atmosphere.

Then look for common themes and pick some small wins early to earn trust of the team.

A few early wins: for couple of managers who had too much on their plate, we did an exercise to delegate to their teams to help them scale. Both are in a very good place right now. For the organization, it was to take all of the organizational initiatives we are driving, tracking it publicly, and running them as sprints which contain user stories. Tracking the work publicly creates org-wide visibility, accountability, and ownership along with some healthy peer pressure for those who currently may be too busy to take on an initiative. So far we have had over 20 people sign up to contribute to things such as rolling out a new on-call process, creating a mentorship program, and resurrecting our dormant BigEng blog which you are reading right now, and where we will share all of the incredible engineering things we are doing here.

"I know that diverse teams outperform homogeneous ones and ultimately build better products..."

Diversity and inclusion is an important issue and one that I take very seriously. On a professional level, I know that diverse teams outperform homogeneous ones and ultimately build better products, not just because the data shows it but because I have lived it. In my last job we had a really special management team which at one point was made up of 5 out of 8 women. On a personal level, I care about this issue as I have seen the challenges impact my wife in her career. My commitment to the business is to seek ways to recruit more diverse candidates into the team.

While working on that, in parallel, I am attempting to create as diverse of an environment as I can with the team we have and make the female voices currently on the team heard. I added the two women who are in Team Lead roles to my weekly staff meeting with my direct reports for two reasons. One, creating more diverse viewpoints adds value to the group, and two, to show the rest of the organization that I am committed to leading an organization that supports all groups. I am ok with doing something that may be seen as controversial by some if I believe it will help the greater good. I fully understand that this may not sit well with male leaders in similar roles in that they might feel excluded. However to compensate I am committed to ensure that they have the access and support they need to make their mark and be wildly successful in their careers here and beyond. This is not a zero sum game. We can make room for more voices without compromising anything. Finally, we are starting to see some good results. After hitting a bit of a lull in hiring, four out of our last six engineering hires across our Austin, SF, and Sydney teams are women along with a few others in other parts of the greater Product & Engineering group.

The Road Trips

SF, Austin, SF, Sydney, SF, Kiev, SF, Austin, SF, SF, Austin.  These were my first 11 weeks. I have 3 kids at home and my wife Sarah started a new job where she was doing quite a bit of traveling right around the same time. We share the parenting duty and are fortunate enough to have an amazing nanny to make it all work, but the first couple of months were a bit challenging on the home front. We barely saw each other and on weekends we both scrambled to take our kids here and there to their activities.

Growing up, my dad used to travel for his job and then come directly from the airport to watch me play in my tennis tournaments. I have a newfound appreciation for what he did and can also fully understand why it was important to him.  

Watching my 10 year old Eli go through the ups and downs of a weekend of baseball, learning how to be a good teammate, handle winning and losing, and regardless of the outcome eating at the nearest Chili’s and goofing off with all of his buddies is incredibly satisfying as a parent (except for the eating at Chili’s). And when I am tired and jet lagged, I get very grumpy at home and become a lot less pleasant to be around. But this is getting better. I am learning how to sleep a bit better on long haul flights as well as to plan for some downtime afterwards on the weekends to sneak a power nap in.

Shit Gets Real

It was right around my 60 day mark where two key managers resigned in a span of two days. This was one of those moments where you don’t quite know where you are going to land. The short of it was after a brief period of everyone involved processing the changes, followed by some heart to heart discussions, several individuals stepped up to take the opportunity to fill the leadership gaps. The teams involved are now running as strong as ever.

Lessons Learned

The first lesson learned was a bit of an eye opener for me in that our decentralized way of doing architecture actually does work very well in practice. Empowering teams (as opposed to a centralized architecture committee) to own their technology decisions along with the understanding that they will iterate on them is a beautiful thing.  It just needed a little fine tuning on the margins, mainly related to written communication.  

The second is that communication across a large distributed group is hard and there is always room for improvement. The third one is that after 100 days I still have a ton to learn around product and technical knowledge to be more effective. I intentionally weighted myself towards the people and processes. That is where I felt my contributions could make the most immediate impact and also happens to be where my personal strengths are. And also probably why I was brought in here in the first place. But I still have plenty of work to do on the product and tech side of things.

What Comes Next

The first 100 days were an incredible, wild ride. There are a ton of things to accomplish but I will share some of the highlights which I am most excited about.

Over the next 100 days and beyond we will be rolling out a new operational framework that will allow us to scale product and engineering through our growth during 2019 and beyond. We have some major technology initiatives that will enable us to become the best open ecommerce platform in the world, hands down. And I want to lead a more structured career development program, where every person in my organization has a career growth plan and knows where they stand and what they need to do to get to the next stage of their journey. And we are going to continue with regular content on our BigEng blog, to give everyone out there a bit of a taste of what we are all about.