This post is part of a short series about my experience in the VP of Engineering role at Honeycomb.

In February of 2020, I was promoted from Director of Engineering to Honeycomb’s first VP of Engineering. Although Charity wrote an extremely generous public announcement, I hesitated to talk about this new role for quite a while as I was figuring out the job. But since 2020, I’ve noticed how little candid writing there is about paths to the VPE role or what the job is really like.* 

I understand why: the stakes for public comment become higher as you move up the ladder, every social media post has the potential to be interpreted as a subtweet or request, and your highest-priority work is often deeply entangled with confidential company and personnel matters. 

Nonetheless, I think it’s useful to share what I can about my experience in the hope that it might encourage others to seriously consider this role, especially those from backgrounds, identities, and genders poorly represented in the VP of Engineering ranks today. VPs of Engineering often have a lot of influence over both company culture and policy, and the decisions our companies make ripple outside of the companies themselves. The whole tech industry would benefit from more perspectives in this role.

Not the plan

I didn’t join Honeycomb with the goal of becoming an engineering executive. I joined to be an engineer (employee ~12), with the understanding that I might go back to a management role when there was a need. 

I had enough experience at early-stage startups to know that, if the company is successful, you’ll probably do a whole host of things as the company moves through different phases. Being attached to a particular job was more likely to be a hindrance than a help to either my success or the company’s. I was curious about moving up the engineering management ladder eventually, but I assumed a VP opportunity would be out of reach for a long time, if ever. 

Instead, I joined Honeycomb because the team seemed incredibly smart and kind, I thought I would learn a lot, and the product seemed like something I’d wanted at past jobs but could never find. Happily, all these things turned out to be true and are still true to this day. 

If you hope to grow into a specific role sooner rather than later, I suspect joining a startup at a later stage (series B+) might be the most efficient route. Nonetheless, I loved joining Honeycomb at series A, even though it has meant working through some of the wandering-in-the-desert phases of the company. (I’ll save writing about those for my post-IPO Honeycomb screenplay.)

The path

In the early days of the company, co-founder and then-CEO Charity Majors managed basically everyone, from execs to individual engineers. In what was mostly a happy accident, Charity and I turned out to be philosophically aligned on most things management, and I have long admired how her insights shape many conversations in our industry. However, we have fairly different backgrounds and skill sets. While Charity has deep experience in the domains of infrastructure & operations, databases, and backend engineering, I come originally from design, frontend, and product engineering, and I take a particular joy in collaborating with product management and ux design. 

We share a lot of experience with metrics and monitoring technologies, although she kind of despises them and I feel a profound affection for them. I’m also a rules and process person — my daily work and even my hobbies often revolve around planning things and managing risk — whereas Charity has a more intuitive, spontaneous style, often shines brightest in a crisis, is allergic to checklists, and is quick to spot when things aren’t working, including when a particular rule or process isn’t serving us.

As Honeycomb grew and the management workload within R&D increased, I was able to load-balance more and more management work with Charity, usually picking up areas where the work matched my background better than hers. I wish I could call out specific milestones on the path, but the truth is it was done in a thousand small steps. A few