Ask HN: As a first-time solopreneur how would you go about hiring the first team I am interested in understanding how would a solo tech founder hire the initial sales, marketing, operations, cyber security and DevOps team members? Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for, how does one start? What questions to ask, what to look for and where to look for the talent? |
Largely, they have the problem you have. They don't know how to hire. We get some initial POC/MVP services up and running, but then it comes time to monitor, secure, upgrade, actually run the software for the long term, and they try to bring in people who can do that, but don't even know what to ask in an interview because they have no knowledge of these fields of practice themselves. The main company I'm working with right now has hired three guys to try and do all of the basic maintenance and daily operational work and they've so far fired all three. They either messed up badly from not knowing what they were doing, or at least realized they didn't know what they were doing, but also couldn't learn, and this company doesn't want to be wasting the money they're spending paying me to be a teacher, and I don't want to be a teacher.
I think my advice would be advice a lot of solos don't want to hear. Unless you're a genius polymath with at least inch-deep knowledge of virtually everything related to computing, which gets harder and harder as time passes and there is more to know, don't try to do it alone. Have co-founders that augment your gaps. Technically competent investors with expertise in how to staff at the executive level so you'll have others with you who at least know what to look in staff and how to hire, or can help you separate wheat from chaff if you're trying to use headhunters.
Also, don't be in such a hurry. Whether it's get more runway, cut costs elsewhere, I don't know, but take your time and do it right. Going through cycles of hiring the wrong person, having to fire them, and then doing it all over again, is disruptive, destructive, and will get you a bad reputation to the point no one reputable will even want to work for you.
Otherwise, your best shot is to get lucky. That happens enough at scale that the market is full of people who got lucky, but it doesn't mean the probability of success is high when explicitly using "get lucky" as a strategy. You can't just look at what the top people did and copy them any more than you can watch Usain Bolt's training videos and hope to become a great sprinter by doing whatever he does.
in a nutshell: for a startup as early stage as yours, you need people. you will figure out what you need as you go along.
You need to know what you are hiring for before you have a chance of hiring the right person for the role.
At this point hiring is an XY problem.
Because your problem is sales, not hiring a sales team.
Good luck.
My guess is that you need a co-founder that can fill the gap instead of employees.
It seems like hiring people is much less risky than marrying them.
Your cofounder doesn't need to own 50% of the shares, you can still act like a "solo-preneur" but you need people fully committed to the success of your adventure.
Before you hire start doing that job yourself to understand it and hire only if you are sure you have to hire someone.
If it is only you then get at least one other smart person to share the job and go from there.
If you hire 5 people and take them “just do it” you can as well give me your money or to any other random person effect will be the same.
They need to be autonomous, flexible, but above all brilliant at what they do.
If you get "average" employees who just wants to follow the specs and receive their salary, they will most likely cost you more to manage than they will create value.
In early stages, you're probably still trying to answer complex questions - and you need people who have the capacity to think outside the box to do so...
As you grow, you can start tolerating people who "think less" and just do what they're asked. You'll have managers to manage them.
In other words, the type of people you need at this stage are the type who could be almost be startup founders themselves. ;-) My 2 cents.
Someone who will take burdens from you and go handle them themselves and don't need to be cajoled, directed every step, motivated, managed, etc.
There is crossover with smart, but that's just a nice to have - responsible is the primary attribute you need here.
Plenty of smart or even brilliant and still lazy people out there that will not fit here.
It seems super weird that you'd literally be in the trenches with 1-2 other people who each have as much equity as 50-100 of you.
Otherwise, I mean, why should someone brilliant work for you instead of a company with much better odds of success?
Clearly, companies do hire founding engineers at these rates so maybe I'm the crazy one. But it just seems wild to me.
I don't think people appreciate how hard it is to go from 0-1. To validate a product/market, get initial customers, before raising, heavily derisks the business and 1% is fair. Sure, you could just start your own startup, but you'll have to go through the brutal glass eating process of doing exactly that, starting a company.
Alignment on profitability and efficiency leads to wanting to be together more permanently anyways.
If they can stick around there may be room for a larger conversation for actual retention.
Handing out equity for a self-funded startup doesn't mean as much especially if the hires don't execute.
Pretty much. I run a bootstrapped SAAS and built a small team over the years. I havae made so many mistakes when hiring the early employees. So many. The biggest mistake: Hire someone who will be a good fit in a larger team/corporate where they have structure and are told what to do. Do not hire those people as your early employees no matter where they come from or how smart they are in general.
You need people who are "almost" entrepreneurial but cannot do their own thing. They love to own things, have autonomy and can wear multiple hats. They are willing to experiment with you and most importantly, move the needle. Very difficult to find especially when you are a nothing startup.
I do however disagree with your final paragraph. We had a few wantrapreneurs who were usually moonlighting and clearly didn’t want to be there.
So for instance try doing marketing yourself for a month. One benefit: you may discover you're good at it and don't need to hire someone, or hire someone freelance or part-time. The more important benefit: when you're interviewing a candidate, you know what you're looking for and can explain what you need from experience.
previous places you've worked are great sources, as are alumni networks, friends and family.
failing that, go become a part of a community like a runner club, rock climbing gym, music scene, maker space, game jam. ideally you do these thing because you enjoy the though.
be prepared to pay people. don't hire anyone you're not confident in (if you're not sure on someone because of pay then go out and find the money [yes, i am aware this is v hard])
Also, completely agree that you need to be prepared to pay folks, unless you are very close with them and they explicitly understand that you haven't raised, and are at an early stage. If you can't pay them, ask for simple advice and ask if you can call on them for help if/when you do raise/have money.
OP - if you don't know what you are looking for, ideally, be comfortable asking what you would think as stupid (or basic) questions. Don't worry, serious and/or good people worth working with or for won't mock you for that. Just because something is second nature to me (a product/sales/marketing person) doesn't mean it's second nature to someone who has a background in finance or systems engineering or whatever. And that's completely OK!!! People love to talk about themselves or their job or their industry, so just learn to ask good questions, no matter how complex or basic.
I myself have been in that situation recently - one of my neighbors has found tremendous success in the area of business I am currently in - so I've been able to pick his brain more than once, and because he knows I'm serious and want his help, he's more than willing to answer any question I have. Find people like this, and yes, be prepared to pay them or offer them equity if/when appropriate.
What stage is your business? Pre-rev, rev, profitable? What business are you in? What part of the world are you located? Are you looking too go remote, hybrid or Co located?
Really you need an advisor if I take these questions at face value.
If you have funds to be able to hire a team (esp cyber security), then you've likely raised money or made money. If you've raised money your investors should be able to deeply help you. If you've made money, I feel like you would know what you need more than anyone here and you should just interview for your biggest problem you can't solve yourself.
> (…) you should just interview (…)
But how would they go about doing that? Where does one find an advisor or the people to interview for those positions as a solo founder without experience in the matter? Feels like that is a big part of the question:
> (…) how does one start? (…) where to look for the talent?
I've also occasionally received random emails from founders, students, former coworkers... and have always found the time for them as a way to try to pay back all the help I got myself from strangers on the internet.
Finding external recruiters that are able to screen for these skills is another option, but such recruiters are few and far between and their interests may not be aligned with yours.
At Toughbyte we do tech recruitment and have helped early stage startups hire CTOs on a few occasions where I have been the one assessing their tech skills and culture fit, but this isn't something that I have yet figured out how to delegate properly to other team members.
When it comes to assessing tech skills, this blog post I wrote is worth a read: https://www.toughbyte.com/blog/how-to-effectively-assess-cod...
Other posts tagged Hiring may also be of interest.
I'm genuinely curious.
The best thing is to know a lot of people and just happen to know somebody who can help you. The second best is to scour the internet and your network for people who are good at what they are doing. Trying to hire your first person on a job board is probably the worst thing you can do.
Rather than start with a position, start with the person and figure out how they can help you given their skills and personality.
This is not the time to standardise your positions, you have to make best use of the flexibility that startup setting provides and use that flexibility for your advantage.
You will have to give them a lot of freedom anyway.
Don't hire people who can't deal with ambiguity and/or need a good precise description of what they are supposed to do. Most of the work is defining what you are supposed to do so you will be getting very little value out of them if you have to provide all of the direction.
If you are starting with a vision and try to force somebody into that vision then you are already fighting an uphill battle.
What worked for me was starting to give out small tasks via <your favorite freelancer platform>, often giving the same tasks to multiple individuals and then decide with whom I am going to stick.
Has been pretty successful for finding talent, not sure how much my anecdote weighs in though.
Working together with friends is something I probably won't do again, it's just too easy to cross damage professional or personal part of the relationship when there are issues arising.
So if you can afford it and have the time, I would recommend starting on freelancer platforms. It also allows you to make mistakes as these relationships do not require commitment from any side. Down side of course is, that you might lose good talent as they are also not comitted to you.
If you really need the second person to do something critical that you cannot do yourself consider a cofounder, not an employee. My 2c.
What you need is a 'specialized generalist' someone who knows enough to set you up for success, get the first few hires, get your sales engine going, get your ops infra nailed down.... but doesn't necessarily want to slow you down when you need to scale out the functions you mentioned.
This is how I operate basically; I help us get to 1, then I replace myself with four or five specialists that can handle those 'departments' as the company really hits its stride, and move on to the next company usually thanks to a referral from the previous guy. It's fun.
Here's what I'd consider
1. Youngish people (40s) who have done some time as a COO at a growth stage or earlier company,
2. Who've been in that role 2-3 times at various early-stage companies in your domain (SaaS operating models are wildly different than consulting services, for example). Also CFOs with diverse/soft skills are good here too.
3. Experienced folks won't work for free. They know the risks, so expect to pay; slightly under market + equity.
i am kind of in this situation myself. but i primarily need sales partners in regions where i want to sell my services, while the rest is done by people offshore (me included)
My stated goal from day 0 is "I'm here to replace myself" which applies a lot of the (good kind of) pressure to install systems or processes that are well-defined, repeatable, scalable, and then hand the whole package off to the new folks.
Some of the people you hire are going to be bad. Maybe they'll just be generically middling, maybe they'll be outright incompetent, maybe they'll misallocate resources and cost you thousands, maybe they'll outright steal from you. Maybe they'll just turn out to be a bad person.
Even if you don't know how to do sales, what benefit do you expect to gain from hiring someone to do it? How long will you wait to see those benefits? What will you do if those expectations aren't met? If you have to fire someone, under what conditions will you provide what sort of severance?
The most important part of any contract is how to break it.
A single bad apple in a new team will drag everyone down, reducing communication, causing silos (as they avoid the bad person) and just generally making work not happen the way it should.
It's marriage essentially.. so date around!
From all my experience, there are very few freelancers in general that are considering employment at all (though the percentage is slightly higher among non-devs). And for the few that are considering employment, you'd would usually have to put a lot of equity into the compensation package to make up for the (usually) significantly lower salary.
As a freelancer I've also offered that option to potential clients/employers, but clients always decline that, citing bad experiences in the past, where they've felt bait-and-switched as after the "trial period" freelancers usually want to switch over to employment.
I run my business for over 10 years and have experimented many different alternatives, for small business with no cash to burn this is probably the best advice one could gave.
Start with consultancy/freelancing reduces a lot the risks
The smaller the business, the higher the risk of hiring the wrong people. You have less money to waste and individuals have a much higher impact in small orgs.
Minimize the risk by "flirting" before commiting to hiring.
For me, generalists with experience (a lot of different specific skills) and have learned how to learn so they can solve problems is key.
A lot of thie hiring in the start, especially self-funded can be a little counter intuitive. The purpose of hiring is to free you up to work on more valuable parts of things, assuming you want to work on those things.
If you focus on hiring people better than you, it will get you more free time.
Some people rather than equity, focus on what folks are really after, payouts. Doing rev or profit share can be easier than dealing with the mess of shares, especially if you don't know if they will be devoted to it long term like you.
For sales roles especially finding someone who can become a better sales person than you, it might involve a rare exception and providing ongoing commission as long as the customer is engaged on the system, and the sales person remains there.
In terms of looking for the talent, if you are looking for fractional assistance before full time, online sites like upwork can help find the people who are ready for something stable.
The book above will give some food for thought and there are others I'm sure too.
Nothing can sink more your company than a bad hire because you can't afford to compete with big companies. Another option is to lose equity in the process, so you get people who actually give a damn.
Until then, outsource to agencies on the expensive side and be quick to fire them if not performing.
https://a16z.com/hiring-executives-if-youve-never-done-the-j...
“The very best way to know what you want is to act in the role. ... In addition, ... bring in domain experts.”
Realistically, early stage startups have a person do all of these things together and learn, they have no budget to hire talent in those roles.
If you're business is that successful without any of it..you may actually not need these people.
You start by doing the tasks you need done yourself. When you learn what is needed and can't manage it yourself anymore then you know what to ask and hire for.
People who try coding for a month and based on that try to hire a programmer make terrible clients/managers. I am not sure this advice would apply to anything that has even a little depth/nuance.
It may well be that you're not qualified to hire marketers or developers, but while there's nothing wrong with getting qualified for things, that probably isn't your priority right now, so you should spend that month on doing things that matter and "simply" get someone already qualified to do that task.
And while there are many reasons why you couldn't or wouldn't hire a friend for that role, using your personal contacts to fill gaps in expertise will be very, very important; because you can't simply buy a combination of expertise and trust anywhere.
Anybody happen to know the link?
How will you be able to discern a charlatan from a good fit to your company, if what they're supposed to be at at is totally alien to you?!
Go to the library, ask around, google. Even if you completely fail at marketing, you've learned something about the skills you're missing. Which your company is missing.
2. Try to get people to read that blog post.
3. Try to get it ranked top 10 in Google for a very specific keyword (doesn’t matter how unpopular it is)
4. Reach out to 10 people and tell them about said blog post
That’s just one example
Yes that's the potential downside. That's why I said "almost" who cant do their own thing. That difference is very slim.
I think an advisor would be an excellent choice in this situation. I have done these things in the past (providing advice) and I think it can be best bang for the buck. Sometimes you just need a third party to take a look at your business and point obvious stuff out. Somebody that already has answers to questions which will cost you a lot if you have to pay with your own experience.
(yes, I know, this was a shameless plug. But I do believe in the services I provide.)
My point was that it’s surprisingly easy to get good connections and advice simply by putting yourself out there and while it’s not the same depth you’d get from a dedicated, paid engagement it can be extremely helpful
Believing that spending a month of high-effort learning will teach you enough of the basics of just about any field that you can flush out terrible choices isn't _that_ ridiculous...
I suppose I wasn't clear, but we don't typically help with the first tech hires, since I haven't figured out how to do it in a scalable manner. I also believe that very few external recruiters can help here, since most don't have the tech skills required.
Fair point about the blog. I probably wouldn't have written the comment if I didn't think that we have relevant useful content there that I could link to.
A point I would also like to make is interest: a tech recruiter/"virtual team" provider might have misaligned goals to yours.
Even if startup founders had time to spare spending a month learning how to doing each and every task they needed to hire for (and trading money they have for time they don't is the whole point of hiring) they'd (i) have no time left to focus on the core business (ii) do a really bad job and (iii) having barely understood the basics, run exactly the same risk of hiring good interviewees with the right credentials that were actually bad at their jobs. Maybe they'd even be more sympathetic to the bad hire because well, he's better than I was
That’s not to say I disagree with your points in general, but just that hiring is every bit as much of a minefield as doing things yourself. In either case you have to understand what is most crucial for the next stage of growth and prune everything else obsessively.
When I started my business (non-tech), i knew very little about sales processes or relationship building from a sales perspective. One of my first consistent customers (disclosure: he is also a close friend) is a sales professional. I learned the very basics of sales, and came to him, asking what were probably dumb or basic questions, but he was more than happy to answer them and also point out where, as the company grew (and hopefully grows!), what to look for in sales people and relationship managers. While I still know little in comparison to him, I know some of the right questions to ask, what to expect from those questions, and what sorts of answers I should be looking for. He also knows that I can call him with deeper questions and to help me evaluate a sales-related situation as it arises, and he'll give me a no bullshit honest answer.
Find people like that.
If you're really motivated to participate in x you should try, if you're a bootstrapping solopreneur you may have no choice, but if you're looking at mitigating hiring risk, a month trying to code/sell/design outside your comfort zone doesn't really move the needle on figuring out how to evaluate programmers or whether your startup actually needs a sales team. (If anything, you're more likely to get the wrong answers from the DIY approach because maybe the sales function actually would be beneficial if it was carried out by someone who could sell...).
That's where you get more insight in less time from leaning on people in your network who actually are marketers or salespeople or product people to get a view, especially if they're not financially incentivised to propose a particular route.
If you want to mitigate the risk that ICs need structure and resources, you focus your hiring on candidates that have worked without structure and resources. But even having a codebase written by someone learning not to rely on Scrum meetings and JIRA tickets to prioritise is still better than having one written by someone learning to code.