Making software and software development teams. Mostly the people parts.

Second Lap

Talking to a candidate the other day who described himself as "being on my second lap", I thought, yeah. That resonates. For me, this is what my career looks like so far after over 20 years in tech:

  • Studied Computer Science at SDSU
  • Worked as an IC and then later as a Director at a retirement planning brokerage
  • Started businesses, cofounded a seed-funded startup, Startup CTO
  • Then back to IC as modern JavaScript, React and Chrome made building for the web fun
  • Enterprise Principal Engineer, doing architecture and systems designs
  • Then back to my true loves: People & startups. Senior EM at a Series A turned Series B healthcare research rocketship

There was a time when my age worried me. Sometime around my mid-30s: Silicon Valley was the hot show, and I was very concerned about aging out and how valuable was a 40-something technologist, anyway?

As turns out: Very much so. Every day I find myself referencing and making decisions from something experienced along the way. Whether it's people management mistakes, making a poor hire, or microservice complexity explosion, having been there, done that gives me the kinds of sniff tests that often lets me smell trouble long before anyone else sees it.

This kind of career path wasn't talked about when I got into industry. Back then the thought was, well, it's one way up the ladder. And if you ever fall off, then you're stuck at the bottom for good. Not the case anymore.

Will I go for a third lap? It's hard to say, but at this point my lean would be why not. I've never lost the deep love for programming and for building that I've had since childhood. Building orgs is fun, and I'd be perfectly happy to keep doing this. And... if an opportunity comes up someday to focus again on writing code? A third lap sounds like a good challenge to me.

Time Is The Toughest Dimension

Along the way, you learn to reason about systems along two axes:

Vertically: the tech stack, generally from persistence forward to a UI.

Horizontally: the capabilities and experiences built from said tech stack.

Time is the third dimension, and it's the hardest to reason about. Spending time reading the blame is one way. Talking to people is another. Usually somewhere in the intersection of those written and oral histories is a clear picture of how we got here.

The superpower is in being able to tell a story, based on trajectory and velocity, of where we might go, and where we should go.

My experience is that most ICs and even many leaders will struggle to see the time dimension clearly.

An Error Can Be The Friendliest Message

If there's road construction ahead, the friendliest alert is a warning: Heavy traffic, take an alternate route.

I can take this information and action it, or I can take it as advice and override it. Because I need to go to a store along the way. Or I live along the road but before the area I know the traffic is. Or I'm just feeling lucky, besides those signs are sometimes wrong and Waze is showing it's fine.

If, on the other hand, there's a giant chasm in the road ahead, the friendliest alert is a big sign saying DO NOT ENTER.

I can take this information and action it, or I can keep driving and fall into a giant chasm like the old Saturday Night Live skits with the driving cat.

Sometimes when designing an interface, we're hesitant to throw an error. It doesn't strike us as user-friendly. Sometimes, though, when the road is out? A big DO NOT ENTER sign is the friendliest thing to do.

Joining AllStripes

Today is an exciting day for me: I've started a new role as Senior Engineering Manager at AllStripes, a healthcare startup unlocking new treatments for people with rare disease.

Choosing AllStripes for my next adventure came down to thinking in terms of a few frameworks. Notably, Will Larson's thoughts on a 40 year career in tech guided me. Working at a high growth org inside a big company like Home Depot enabled me to optimize for meeting lots of people... I met hundreds if not thousands of technologists in my 5 1/2 years with Depot. AllStripes, on the other hand, is small enough to be on a first name basis. Meaning I can be Jon O or even just Jonny or Jon again, rather than Jon Oropeza who's one of many engineering leaders named Jon or John. What I'll be optimizing for at AllStripes is rapid learning and meaning from the mission we're on. I've been thinking all year about more meaningful work, something towards the heart of the hard problems I see facing the world. Working to advance healthcare research is a great fit in that regard.

The path to AllStripes was through a focused search that I undertook this fall, and following something similar to Jason Crawford's template I was able to target roughly ~30 orgs, mostly in that Series B - Series D range, each with an appealing mission. I met with the 7 out of ~30 that had openings for engineering leaders. I got more than one offer, and it was AllStripes that won my heart, even though we're earlier and smaller than I'd initially intended my next opportunity to be.

I have a lot of thoughts on leaving Home Depot, if you're interested I collected them in a Medium post that seems to have resonated well. Actually, looking at the reading stats, this might be one of the most read things I've ever written, probably up there with times when my work was published in various San Diego area periodicals back when I was actively writing fiction and poetry.

I'll likely be pretty quiet through the Holidays, as I'll be focused on my first 90 days and getting settled into the team at AllStripes. Next post should be some thoughts on planning for 2021, and in particular a collection of the frameworks I use to retro the year that was and plan the year that will be.

In the meantime, if you're interested in working with me either again or for the first time, AllStripes is hiring.