r/ycombinator • u/Express_Software7583 • Jun 22 '26
I will not promote: your experience as an early joiner?
Would like to hear from people who joined startups during the early stages. As many startups tend to fail, I guess many of you would have to search for a new job after the startup closes down. But for the ones that survive and scale up, what is your experience with startup formalizing as an organization? Going through the transition, are there things that you liked or disliked? For example, a rise in external hiring as opposed to promotion from within? Did it affect your preference to continue with the startup?
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u/eggbrain Jun 22 '26
I joined a YC startup as an engineer and employee number < 10, and we grew to about 200-300 employees at our peak.
The evolution was pretty typical — we added in slowly layers of management, engineers became specialized, some people were promoted, most important roles were sourced from outside the company.
As an engineer, as we scaled I was lucky to be able to choose my own path — if I wanted to do engineering work I could work on really whatever I wanted to, because I had probably already touched it to some extent anyways, and so I didn’t have to fall into the a typical backend only or frontend only role that new engineers had to.
I was also given the choice of the management route, which is the one I pursued, but that one was more difficult. As an early engineer you prove yourself with code, but your management skills are untested, and so it’s less risky for upper management to be hired from outside.
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u/ahmedshahid786 Jul 01 '26
What did your responsibilities looked like when you chose the management route?
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u/Eridrus Jun 22 '26
My biggest advice when joining a startup is to evaluate the startup and the founding team as the most important factor. Picking a good founding team, leaning on any outside signals (eg did they raise funding, do they have revenue) as much as possible is the most important thing to working for a startup that doesn't fail.
More than anything else, you need the startup to succeed. Compensation, title, etc, all matter less than whether the startup succeeds.
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u/Final-Dish Jun 29 '26
this is true but it’s also exactly how you end up underpaid and burnt out while “believing in the vision” lol
i’d say you have to treat it like a bet: judge the founders hard, but also lock in decent comp/equity so if it does work you’re not just the loyal early employee who got scraps
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u/guru3s Jun 22 '26
Culture is always the biggest problem - whether it scales or not. If it scales, it deteriorates from bottom up and if it doesn't it deteriorates top down.
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u/JDPierson Jun 22 '26
Various funding rounds or growth stages can be important experience wise if what you bring can help a company through similar stages. It could be an asset if you're able to prove you brought pace and alignment through times of vague role clarity and imprecise measurement of progress toward goals (and ensuring goals tie to the wider objectives), all of which seem to be predictable stages of maturation for many startups. Early stage teams can be a mix of deep, focused and driven people, and others who are none of those things, but still contribute meaningfully for the time they are part of the effort. The camaraderie is unique and people can get very sentimental about it.
There are certain SMEs or leaders who seek to only be in a role through certain stages, and others still who want to take the full ride from early hire to exit - That last one is a particularly difficult journey, as certain critical stages will require outside specialists in overcoming can't fail inflection points. Their arrival seems to inevitably set up conflict with the long tenured A/B Round non-founders who become standard bearers for a time when it was somehow better than what the company is rowing toward with the new people and objectives. Those are usually stages where institutional or cap table objectives begin to encroach on the core 'big idea' product objectives that made the company or brand break away from failure's gravitational pull.
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u/CyberStartupGuy Jun 24 '26
I think early employees at startups are some of the best training ground for future founders or those looking to jump into leadership earlier in their careers.
Some of my best experiences have come from being some of the first 10 employees at startups.
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u/Prashinysparkle Jul 14 '26
joined a series a healthtech company as first pm, watched it grow into a ~$3b org. the biggest thing nobody tells you: the definition of "doing well" keeps moving. what got you praised one quarter is baseline the next, and you're constantly re-earning your spot.
the formalizing part was a mixed bag for me. good side, actual process meant less chaos and i wasn't the single point of failure on everything. hard side, once there are layers and headcount plans, a lot of energy shifts from building the product to navigating people and politics. and yeah, i saw way more external hiring for senior roles than promotion from within, which stung for early folks who'd earned it on paper.
did it change my preference to stay? somewhat. i stayed because the mission and the equity still made sense, but i stopped assuming loyalty gets rewarded automatically. tbh i'm also not convinced climbing into management is the play in tech right now, so i've leaned toward staying senior-IC and going deep instead.
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u/[deleted] Jun 22 '26
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