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SurgicalOntologist
Jun 17, 2004

Hi thread, not going to weigh in on the ASD discussion, and I don't know if my experience qualifies me as an "oldie" but I guess that's my question. How does the industry look at profiles whose only experience is as technical co-founder / CTO of a (relatively unknown) startup? How can I convey that my experience is serious? Is it? I'll give a little synopsis but I'm curious which factors are better to emphasize, e.g. team size, direct involvement with the stack, product complexity, etc.?

Obligatory preface, I'm just posting this for curiosity and it's not indicative of anything happening with my company. Please don't doxx me, if you want to connect outside SA send me a PM, no need to internet sleuth me.

But on a personal level the situation is that I moved my family abroad for this company, with a clear timeline from the beginning. My wife's career, aging parents, etc., make it hard to change that plan, so we're looking at moving back to the US in 18 months to two years. I've been open about this timeline with the rest of the founders/management and the plan is to expand to the US so hopefully it all works out. But obviously anything can happen in that timeframe, whether positive or negative for the company, that might make it a transition point in my career. At minimum, I should be able to price myself honestly.

I've been out of the US, I have little professional network there, and I know how "CTO" experience can be perceived if the company isn't known (although I do think our tech has "curb appeal" and sounds impressive from the first explanation. No crypto-esque bullshittery). The range of outcomes for me on the market feels huge; I'm not sure where I fall compared to more typical career trajectories. I'm not super ambitious --- even relative to cost of living a junior US salary would probably be a pay bump, plus my wife would be able to work again, so I'm not shooting for the moon but I want to aim for what I'm worth. On the one hand, my 5 years experience feels like 20 years. On the other hand, part of me feels like I never had a real job. At least, I've never been on the market before.

Anyways, to keep it relatively short (fake edit: lol) here's the blurb I wrote for the Pragmatic Engineering talent collective (I didn't get in).


I started with very little experience (a non-CS PhD then a post-doc where I mostly acted as a data engineer). Of course, I learned a lot the hard way and I've always been an autodidact but I did try to secure mentorship from some advisors over here, and I was able to hire some amazing developers I learned a lot from. We also learned a lot together, particularly regarding Kubernetes. We needed massively bursting workloads, so we tried Kubernetes with autoscaling and it just worked really well after very little effort, and it grew with us. It really clicked for me a couple years ago (around the time we finally had a product) and since then I've been daydreaming about reimplementing part of our stack as a Kubernetes operator, or building a true IDP, that kind of thing. And I did do what I could in that direction, but we're talking 5-10% of my workload. Haven't hired any DevOps or SRE (although hopefully changing soon) so it's been all me plus a couple of my early engineers that also learned by necessity.

So for my next step I'd love to join an established SRE team, or join a mid-stage company with the goal of building a platform engineering team, or maybe just a developer role in a company with a cloud-native product. Hell, I would even consider trying to start consulting and look for gigs helping companies get set up in Kubernetes, although I'm not sure I have the network for that.

Anyways, any thoughts on how to level myself, or tips on my blurb, or advice in general? And, uh... fries and a coke please.

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SurgicalOntologist
Jun 17, 2004

bob dobbs is dead posted:

cto of 15 peep team usually translates to line eng manager or staff eng in bigger company land

That's cool, maybe I have some imposter syndrome because it's higher than I would have guessed.

Edit: also feeling imposter syndrome for writing so many words

SurgicalOntologist fucked around with this message at 18:20 on Apr 25, 2023

SurgicalOntologist
Jun 17, 2004

Destroyenator posted:

As other said, you could probably swing line manager for devs/sres if that’s what you wanted but if you’re hired into somewhere with that role it would be less hands on keyboard work (which it seems like you’re used to). Your other option would be as an IC like you described, maybe in an SRE/k8s role.

You should think about whether you would be happier inheriting a team of SREs and dealing with business priorities vs their vision for the tech, implementing processes and generally working to develop a high performing team; or joining as someone on a team like that getting your hands dirty in kubernetes and working to enable the teams your team supports, making technical recommendations etc etc. Both paths have the the landmines of who could end up being in the team, but they can both be fulfilling depending on what you want.

Well, it's been gradual but for the last ~2 years I've done relatively little "hands on keyboard" work. Probably in my description I've overemphasized the IC aspects of my role, whether because I'd like to move more in that direction (I'm torn, but probably yes), or out of impostor syndrome.

Anyways, thanks for the more detailed thoughts. Your two paths are just manager vs. IC, right? The way you laid it out, definitely IC is more appealing, if I had to decide now. What I would really love is a kind of "internal founder" role where I could be a sole IC in platform engineering / SRE then eventually get to build a team out of it as the company grows. Although I've never had a team lead or engineering manager over me, only external advisors/mentors, and part of me feels I need that experience and it would be a mistake to jump into another role with no real technical oversight. And of course this is all just daydreaming as who knows if I'll be in such a position to be able to take every factor into account.

I guess one thing I wonder is with respect to placement, sure maybe a CTO at a company like mine can get up to Staff level, but if I'm doing somewhat of a career transition and moving to SRE for example, which yes is one of my responsibilities but I realistically probably devote 5-10% of my time to that and I'm entirely self-taught, never having hired someone in that role or even worked with an SRE in any capacity. Or maybe keeping our services up and running is track record enough :shrug: I could certainly talk for hours about the challenges there, tradeoffs made, strategic considerations, etc.

A completely different topic, but the more I think about it the more I dread combing back to the US, but more for quality-of-life than career reasons. :ohdear:

SurgicalOntologist fucked around with this message at 10:37 on May 2, 2023

SurgicalOntologist
Jun 17, 2004

Destroyenator posted:

Pretty much, yeah. I think the struggle you may have with the internal founder role is that a company of 30-50 people hiring their first ops/sre person probably already have some level technical leadership but would be looking for an technical expert with lots of experience to put them on the right track on the ops side. You sound like you wouldn’t be as confident in that area, and you’re up against senior sres that have decided they don’t care for management.

Makes sense, and kind of what I anticipated with what I added in edit.


Appreciate your thoughts, gives me an idea of what I could encounter.

SurgicalOntologist
Jun 17, 2004

I don't think computer touching is the problem though, it's capitalism. Source: have had other jobs.

If you can support yourself off your hobby, that's the ticket, although it stops feeling like a hobby pretty quick when there's the pressure of supporting your family behind it.

SurgicalOntologist
Jun 17, 2004

At my startup (15 engineers) we use both Python and Kotlin in different services. I come from Python but after a couple years I have to say I really prefer Kotlin.

Of course, two backend langs at our size causes some organizational challenges, but that's another post.

Been tempted to learn Go as we do a lot of "Kubernetes-native" crap and it's more or less the only language in that community, but I've resisted so far

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SurgicalOntologist
Jun 17, 2004

I have an engineer that I am promoting to Staff Engineer, he will be the first in our organization (15 engineers), and he has already organically started to take a more cross-team role but the idea is to keep pushing him in that direction.

However, he has a bit of imposter syndrome and doesn't want to be in the position that people are only listening to him because of his title, and he wants to wait until he feels more like he's earned it before announcing it. I of course told him he already has earned it, not only with me but also with his peers, and they are not going to be surprised. Maybe there will be some grumbling but I don't think his concerns are warranted. I think I basically got him past his fear but I also wanted to ask here about how to handle these situations. We're a small company, mostly seniors, and most of them humble and cautious so it's hard to get people to step into more leadership roles when we don't really have examples of that to draw on within the company.

The other aspect is that his day-to-day role actually won't change so much now, we originally were planning to be ~25 engineers by now in which case I wanted to pull him from his team altogether. But we scaled back our growth plans so he is still needed on the team. In fact we already have a problem of capacity as we are in the middle of some big architecture decisions, build vs buys, etc, so his team has slowed down somewhat from his (and some others') participation in those discussions.

I guess I don't have any specific question just thought I'd share the experience as it's the first time I promoted someone to Staff.

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