Ask HN: Joining startups of different sizes/different roles

Ask HN: Joining startups of different sizes/different roles

2 by grvdrm | 2 comments on Hacker News.

I am asking a question that oversimplifies lots of things about companies, teams, and other aspects of evaluating new roles, but here goes. I have two offers from tech start-ups that are quite different from each other: [1] 50 person company. $50M+ A. Selling cybersecurity software to financial services. Sales role, though I'm quite technical, so focused more on that flavor of sales. This is the CEO's third company, with two prior successful exits. [2] 8 person company. $10M seed. CEO is a friend. #2 (in seniority) in company most likely but less structured role, probably focusing part on product, part on sales, with key goal to help boost the insurance knowledge of the company. Helping build the company up and sell/iterate the product that is a real-time data reporting platform for insurance MGAs. I think of it as a connectivity and data business rather than a SaaS platform (link: https://ift.tt/UumTHFn) My current role is sort of analytics jack-of-all trades. Sometimes code. Sometimes presentations of critical numbers. Sometimes product mgmt. I work within an actuarial team but I'm mostly a technologist at heart that accidentally fell into the analytics world within insurance. I've received a LOT of advice. Probably too much. Two things I hear are 1) an 8-person company will be a shit-show and not a good experience for my first adventure in start-up world, especially coming from a large legacy insurance company, and 2) sales in start-ups is easily the least defensible position - not as "valuable" as engineering and product. Is any of this advice good? Is an 8-person company going to be a shit-show based on the wisdom of this crowd? Is moving into sales in a start-up from a quite specialized and stable position a silly move? If I'm looking to spend the rest of my career in/around start-ups, is one of these two roles better than the other? Maybe I'm missing the forest for the trees but I am trying to gather some feedback from a larger sample of folks. Thanks!



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