Ask HN: Joining startups of different sizes/different roles | Hacker News Reader

Ask HN: Joining startups of different sizes/different roles

2 pointsgrvdrm7 comments

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://www.insurancebusinessmag.com/us/news/breaking-news/what-is-an-mga-115496.aspx)

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!

> 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

There is a lot to be learned from shit-shows and even sinking ships and the experience can be invaluable to your career.

> 2) sales in start-ups is easily the least defensible position - not as "valuable" as engineering and product.

If you are confident in your ability to this shouldn't truly be an issue. Sales is also often a crucial piece to a startup that is often overlooked and ripe with opportunity for the right people.

---

I'm not sure what exactly you are looking for here. Only you will be able to make this decision. Neither is wrong and it sounds like you may just be seeking validation. Regardless, don't look back too hard and with much regret no matter your choice.

I'd personally make the decision based on the people that I'd be working with and my interest in the work/sector. Even the perfect position can suck if you dislike the people that you work with or don't believe in the product.

Thanks, and yeah, my post is a bit open-ended as it's probably obvious I am struggling with the decision and/or with a framework for the making the decision.

Question back to you: thoughts on how to weight my own familiarity with the core product? To provide some color on the question - I deal with one end of the problem addressed by the 8-person company on a day-to-day basis. That experience has drawn me to the opportunity but also at times increased skepticism. By contrast, I'm less familiar with the problem addressed by the larger company but think the team and the market are ripe for success. So, I'll need to really learn and embrace that problem to sell something that tries to solve it.

You will learn a lot more in option 2. Things you can't learn from books, videos or podcasts.

However expect to be more stressed out.

It all depends what you prefer. One option isn't better than the other. Just pick your poison.

I once tried to start my own company. It didn’t last long but the experience has made me want to try again at some point. Do you think that one of these options provides me with a better platform to make that attempt?

Choose the company that is on the best path to commercial success.

I've heard that comment too. Let me ask in return: why use that a decision-maker over or instead of anything else? Honest question!

You want the job to still exist in 6 months, right?

Reply on news.ycombinator.com