March 2021 Archives

Staff Engineer

Last August I was promoted to Staff Engineer at HelloSign (Dropbox). That parenthetical is important, which I'll get to in a bit. If you've been closely following my career, you noticed that I was promoted to Staff Engineer at HelloSign back in July 2018. So how am I getting promoted again? To the same title? Well, the bit you missed is that HelloSign got bought by Dropbox in February of 2019. Now that we're two years past the merger, here is what happened to my title in the last three years:

  1. July 2018 - promoted to Staff Engineer at HelloSign! I honestly hadn't heard the term 'Staff engineer' before then. It was a welcome surprise.
  2. January 2019 - word breaks about the merger. Eek.
  3. February 2019 - my merger-packet sees me move from Staff Engineer to IC4 (Lead). Apparently, Staff Engineers and Vice Presidents were the two titles Dropbox wasn't letting in. My pay get a 5% bump, and I get my first-ever Restricted Stock Unit grant (they really wanted me to stick around).
  4. January 2020 - Dropbox has their performance review cycle. Because all of the HelloSigners have less than 12 months tenure (merger was in February, remember), none of us get promotions. I start actively working towards a Dropbox Staff Engineer, by clawing my way into cross-organizational meetings where I can.
  5. March 2020 - pandemic, flash crash, market turmoil, suddenly working from home for everyone, mass uncertainty.
  6. July 2020 - mid-cycle performance reviews, with upper management telling everyone that due to budget reasons we'll be promoting half the people we normally do.
  7. Late July 2020 - promotion lists come out, and a lot of HelloSigners are on it! Yay! Including me, to Staff Engineer. This surprised me a lot because I was expecting the January 2021 cycle to be the earliest that could happen. This happened because I was functionally a foundational engineer for the platform/devops side of things, had incredible system intuition (you get that after 5 years working for a place), and knew how to communicate. Promotion comes with another 5% pay bump (geobanding; I'm not in the Bay Area, I'm in the low-cost middle of America) and a sizable RSU grant.

Which brings us to now, half a year after the promotion. I'm asking myself what has changed?

First off, being Staff at a company with 50 engineers (HelloSign 2018) is quite different than being Staff at a company with over 10x that many (Dropbox 2019). Those two engineering organizations operate incredibly differently. When Dropbox said that our Staff engineers wouldn't get Staff, this is why: to be Staff at Dropbox you have to have cross-org impact, and by definition freshly merged HelloSign had no cross-org impact. QED.

When our team finally hooked up with Dropbox SRE (they don't do Devops) we learned what 10x scale means. The role our team of less than 10 people played in the HelloSign infrastructure was filled by 10+ teams in the Dropbox infrastructure. For individual Dropbox engineers it meant most were in a tiny, well-constrained box as compared to the wide scope each of my teammates enjoyed.

More importantly, 10x scale means that Dropbox infrastructure-engineering was writing new distributed systems, where HelloSign infrastructure-engineering was wiring together of-the-shelf distributed systems. Very different scopes and job duties, and why this new IC5 probably couldn't pass their IC2 coding pre-screen well enough to get in front of an actual person.

Second, HelloSign hasn't had a Dropbox style Staff Engineer before, so I'm kind of inventing the role as I go. Functionally, I've taken the title as official sanction to voice my opinions and gather people together on my own authority. Before, I was more likely to work through channels and try to get various managers to assemble a process to solve a problem. It's now my actual job to influence strategy, rather than focused on how to implement strategy.

Doing these things on my own authority has worked solely because the managers involved are letting me. Without that support I'd be doing the things I was doing before the promotion, but with a bit better pay. This applies to managers on the Dropbox side as well, without their invites to process-meetings IC5 would be a promotion in name only.

I was involved in some strategy work in 2019, along with the other former-Staff engineers. But since August I've leveled up, out of my exclusive focus on the HelloSign org and starting to take on strategy work inside the whole Dropbox context. In key ways, I'm now in the room where it happens. I've wanted to be here for years.

Third, where I fit in the overall multi-year strategy for HelloSign is not well defined. We had a terrible run of luck in October 2020 that resulted in several highly visible availability incidents, which resulted in a tiger-team to fix that shit and also make sure we don't get that bad again. This has been working, our SLOs have been 100% passing for the last three months. The work of rebuilding trust in our users takes far longer though, so we still need to be sure our future design focuses on availability.

The interaction between Product Management and Engineering Management is still somewhat opaque to me, and I need to fix that. My team only works with Product Management indirectly, when Engineering comes to us for support building something Product is pushing for. My role in software features is a bit iffy, since rare features involve my domain. But when they do, I should be there. I still don't know the correct attention-split there. Currently our pre-merger CTO is doing all of that strategy work.

Fourth, our org has room for another Staff Engineer on the software side. I recently asked myself if I'd left any marked trails for HelloSign's second Staff Engineer, and found that I hadn't. My HelloSign-specific strategy work is a bit elevated from where it was pre-promotion, but not by much. My Dropbox side is rather different, but that's more a reflection of Dropbox SRE - something a software SRE wouldn't be involved in anyway.

I'm a bit uncomfortable with that, but that's part of what comes with doing something no one else has done before. My management now knows about the lack, and says they're going to work on it. Meanwhile, I'll be pushing my nose into more strategy work.