Ask HN: First 5 People at a Startup... who? why?

Almost no way to answer that, because the number of founders, their skillsets and experience all changes what the first hires look like. So does the type of company, market, bootstrapped or raising etc. For bootstrapped companies, typical first hires are product focused (tech.SAE), sales/marketing (usually combined at first w/a founder doing a lot of sales/closing), administrative to help manage day to day tasks, manage HR, handle bookings, scheduling etc, and outside support for legal, accounting etc. People sometimes try and have a founder do all the admin tasks but it isn't worth it, pay someone $15-20/hr (even part time at first), you'll free up your skills.

If you are raising money, then you need your first few hires to have some attractive traits that will make investors confident you can deliver what you say. I'd say product/tech is critical of course, but then next is someone who can help commercialize the product and get it in the market. e.g. if a founder already has existing relationships in the market that solves that commercial side usually, if not s/he needs to hire someone who can help ease that entry into market.

Although I'd say there are just too many variables until you know the founding makeup, market and finances. I can give at least 3-4 more examples of different people to bring in under different scenarios, and I'm probably only hitting a few.

Recruiting depends on the type of position and the skillset needed, you'll find you need to recruit from different sources for different people, IMO there isn't a one size fits all way to recruit across an organization. As for how do you pick them, pick intelligent people who are good puzzle solvers and self motivated. It isn't that hard to figure out during an interview if you can avoid the trap of the typical ego based interviews (especially when hiring engineers).

This question is sooooooo relevant to me (sorry to stress on the "so").

1. This is the hardest one but all the 5 people MUST share your vision for the company and product/service. If they don't, you may still be ok but will be a long ride for you alone because they will just be employees who want to clock out at 5 PM. Again, nothing wrong overall but first 5 people should have more skin the game and must have that attitude. You also need to try and compensate them the best way possible.

2. I would look for behavior more than skills. Hear me out. I know that skills are needed but to build a company, you need people who have the correct attitude and mindset. Look for curious, always looking to learn, hungry to achieve something type people who don't need to be always told what to do. Again, you have to compensate them as well as possible. Skills can be learned but attitude/temperament/ambitions cannot be.

3. Kinda contradictory to #2, but 1 Person should be very skilled/experienced at the product/service/business domain. If that is only you, it's fine to start but need 1 more. But again, 1 person other than you at start is fine.

4. Look for previous track record. Just because someone says they are very ambitious doesn't mean anything. Ask open ended questions. Instead of asking "so do you learn using youtube", ask "what do you do when you cannot figure something out on your own" type questions. Look at their body language and how they go about solving problems.

5. People who care about Titles are usually not a good fit for early employees/partners. If prestige is important to them, they can be an employee some day but ideally not the first 5 hire.

Source: Bootstrapped founder for 6+ years who has done terrible overall in finding the top 5 people based on what I wrote (but I learned the hard way) but still made it to a team of 15+ and counting.

Someone very smooth in face-to-face sales/marketing/business development and public speaking who really believes in your product and isn't embarrassed by anything (as in 'ready to make fun of themself', not shady). Invaluable at trade fairs, in talks with investors, etc.

You hire the people who free the CEO/Founder to not have day-to-day responsibilities. Who those are will differ depending on what you are trying to do, but no startup can grow when the CEO has to be "in the office" just to keep the lights on and the engine running.

It depends on the business and the top-level organization you are thinking of, but it is worth looking for someone with experience in accounting / legal, instead of leaving considerations like that for when the company is larger. Someone with experience as HR director / senior legal counsel / startup CFO / etc; i.e., demonstrated ability to take responsibility for keeping the company out of legal and ethical trouble.

I have worked at two small startups that started out by outsourcing all HR/legal/accounting stuff to staffing agencies or independent contractors, and it resulted in missing paychecks, minor lawsuits, severely botched contracts, and can lead to serious problems with company ethics and employee retention.

The first couple of hires should be someone with good knowledge (and contacts preferably) in the chosen market for business development / customer success, and then someone with good all-around tech skills as a first engineering hire (assuming you have a technical co-founder as CTO who took the product to MVP level). After that it's entirely driven by who the product is for - if it's a straightforward tech product for B2Bs you're going to need more product and sales than tech, but if it's a consumer app that needs to scale fast then you'll have to push in to tech hires rather than sales.

I would advise to hire for your weaknesses in everywhere but sales (you should be leading that even if your an engineer).

Look for people who are excited about what you are doing, will commit, are comfortable learning new things. It's going to be very hard and early employees will wear many hats.

Ideally you can ask people you have worked with before and trust.

Someone that builds the thing, someone that sells the thing and someone to handle finances. You dont really need more than 3.

Start with what you do.

What am I bad at and needs to be done better? Fire yourself.

Hire someone who is good at it.

What are they bad at and needs to be done better?