Ask HN: How to grow as an engineering leader with mid-level hands-on experience?

[quantamiser]

I worked in a startup from its inception until acquisition 7 years later. I started young as an engineer and did everything required to make the company successful - code, take support calls, conceptualize the product, go for sales pitches and meet with customers. I understood the levers of the company - employees, product, clients and was acknowledged as a good leader. When our team was growing I jumped to fill the gap of an engineering manager even though I didn't get the chance to grow via the typical engineering ladder of SDE 1-2-3 > TL > PE/EM. We had 20 engineers at our max size and my performance (getting things done, fostering team culture) was quite good. The CEO and the tech architect helped to take decisions on tech architecture whenever my skills were not sufficient. Together we built a great team and a profitable product.

I have an amazing experience building a company, but I am struggling to figure out what my next role is. Larger companies (50-200 sized company) don't think I am good enough for EM/Director of Engineering role as I haven't had extensive hands-on architectural experience. Is it normal for managers to have more breadth experience than depth? I understand I cant ramp up overnight. Assuming that I don't want to startup in the next few years, how do I grow from here?

[BayAreaSmayArea]

I'm largely in the same boat. I was part of the founding team, architected our systems, wrote a good part of it, and eventually look over leadership of the engineering and product teams as the CEO had to focus on more external matters. I played the SE role on any meaningful call, worked closely with marketing, and even did sales directly a couple of times landing us an LOI at a critical time.

We had an "ok" exit, not enough to never work again by any means but it put some decent amount of money in the bank.

After riding out the acquisition for a year I've been looking for my next role and it feels like I don't fit in anyones box well enough to get the nod. Besides landing an exec position at a startup with funding, the big tech companies of the world seem like the only place to get good compensation for that expertise. From what I can tell, the big tech places don't seem to be interested in hiring people from startup-heavy backgrounds nearly as much as they used to be.

My approach is to try to reestablish some networks, and tossing resumes are interesting job listings. But the reality is that almost no one is getting hired for great roles without a warm intro to a hiring manager. Dusting off the old personal website never hurt either, it might at least let you get into the right kind of conversation after the warm intro.

It feels like I'd be in a great position to start a startup but with spouse and young kids its not the right time (especially now) to do that sort of thing.

[quantamiser]

I can totally relate to your story. After reading your experience I am pretty sure there are many more like us. I played a key role in the growth of the company and was called a founding member on many occasions, but without a formal "co-founder" or CXO tag, it gets difficult to get an executive role in slightly larger companies. I guess starting a company is the most obvious option (assuming there are no other constraints)

[BayAreaSmayArea]

From what I can tell even with the title it doesn’t matter. I had CTO label and had our companies PMs reporting into me as well. Folks at bigger co’s just don’t seem to care and don’t put value in the experience gained from “leadership” positions in startups.

From what I can tell you can still greatly increase your career velocity as an IC by doing a startup for a few years. It quickly falls away for management roles unless your company hits a big win AND you had a very publicly facing role, in which case the career boost isn’t very needed due to the big win part.

[laurentl]

I would start with a basic question: what do you want to do? Your current job let you explore a lot of topics and roles: which did you like best? Which do you see yourself pursuing for the next few years? Your post seems to imply that you’re looking for management roles but it’s unclear as whether it’s because that’s what you like to do or because that’s what you feel you should do to grow your career. Word of advice: it’s much easier to have a successful, fulfilling career doing what you love than eating shit every day doing something you don’t like (management, architecture, product, whatever) but that you think is good for your career.

Once you’ve figured out what you want to specialize in (and make no mistake, in a larger company you’ll have a narrower role than in a startup), write your resume around those skills. Market yourself (write a blog, try to speak at conferences, etc) as an expert in that topic. Identify what shortcomings you still have and work on them through side projects, reading books, taking an online course, etc. When you get to the interview stage and people point out your lack of expertise, explain (better yet, demonstrate through relevant examples) that working at a startup has taught you to pick up new skills quickly. Convince your future manager that it’s in her benefit to recruit someone who knows how to learn new skills rather than a one-trick poney, even if the poney is very good at its one trick.

[quantamiser]

The answer to "what do you want to do?" - Long-term I want to start a company. Financial constraints and the current situation are not well suited to make decisions in that direction. Short term I want to continue to grow in management roles and acquire the skills needed to get closer to my long term plan. The approach you mentioned definitely helps. Thank you so much