Can't speak from experience, but my recommendation would be to never hire someone to do work you've not done yourself. (I believe Joel Spolsky mentions this.)
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.
1. list all the people you know in each of these sorts of roles 2. ask them to either join you or if they know anyone who might be up for it or if they would help you hire someone by being your capability sense checker 3. if you can't drag together a rag tag team then you need to go out and meet more people
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])
There's too little context to give meaningful advice here.
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.
My advice would be to find advisors who are experts in these skills and have them screen for them, while you do everything else. Pay them for their time in cash or options. Make sure to hire senior level people first and then have them screen for these skills in subsequent hires going forward.
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.
That's a tough problem, regardless how you approach it.
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.
I started recently (2 years ago) and running a small consultancy, and using part of the revenue to build my own product.
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.
Ideally, for first 1-3 hires you hire someone to do the job (most of which) you can do yourself. That way you buy speed, not capability.
If you really need the second person to do something critical that you cannot do yourself consider a cofounder, not an employee. My 2c.
Scale from 0-1 kills so many companies so I'm glad you're asking at this stage.
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.
Ask yourself if you really need all those positions. How much dev-ops and security can you possibly need? That can be shared responsibility until you're much larger. Same with sales - you, as the founder, should be doing most of the sales early on. Its expensive to hire and to fire as well.
Figure out your criteria for failure, and what to do in response to it, in advance.
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.
I haven’t done it myself so I can’t speak from experience, but Rob Walling’s book “The SaaS Playbook” has a whole chapter on hiring and building a team. I found it insightful. The whole thing is a quick read/listen and I thought it was worth my time.
Regardless of how smart someone is, don't hire assholes.
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.
In my 25yr experience as a serial entrepreneur, never hire full-time until they consulted with you for at least 6 months. So many factors can go wrong that are not related directly to hard-skills.
It's marriage essentially.. so date around!
You are over complicating. Start with one person and grow from there. The 1st person is the most important
The book buy back time by Dan Martell has been one of the more interesting and actionable books I've read in a while.
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.
I would advise you don't, until you have way more money than needed so you can buy really outstanding candidates.
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.
If I were in your position I would start with people I know personally and I would define success criteria to hold them accountable against. I would evolve that success criteria as the mission evolves and use that as a frame of reference in hiring the next people. Prior experience in leadership and holding people accountable is required.
Echoing several of the comments here about learning by doing, I think Ben Horowitz’s “Hard thing about hard things” may recommend that too. See section (and blog post) “If you’ve never done the job, how do you hire somebody good?” with pitfalls:
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.”
Ask people who have hiring experience in your network to help you by sitting in on face to face interviews. Same goes for a mentor if you have one. Try to prioritize hires who'll make that work easier.
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Read Peopleware. It’s more about finding teams that gel than individual high performers. Makes the task even more challenging, sadly.
By having a good business, giving good equity and salary and hiring top talent.
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.
Check the books Traction and Who, you could make a score card for each position based on your business goals.
> Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for, how does one start?
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.
I don't think there is a good answer to this, unfortunately. I can't speak as a "solopreneur" because I'm not that, but I'm a consulting engineer doing platform and infra-layer work for small businesses that don't have the resources to do it themselves, and I can at least say where and why I see them fail.
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.
If you really don't know anything about the skillets, maybe a consultant specialized in standing up startup teams would be a good start. After that, look for people genuinely interested in the problem domain or in their specific craft.
just hire. you will figure it out. a lot of people i know often wait for the 'perfect' candidate to show up at the door in a halo of divine light. aint gonna happen. most of the 'A-players' on my team currently were hired less on technical chops and more on un-measurables like 'sincerity', 'attitude'. these same people, now, with the benefit of decades of working together, would not hire themselves as they were when they joined.
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.
Doing those things yourself is the simplest place to start.
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.
> Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for
My guess is that you need a co-founder that can fill the gap instead of employees.
Good write up! Agree with the top comments about hiring smartest independent people earliest
A thing called the Competency Framework can help.
Watch Alex Hormozi on youtube
There is advice from DHH and Jason Fried I believe.
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.
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If you're starting, you can hire some head hunters to do the job. Then make mistakes by hiring bad people so can you learn what to watch out for when hiring talent in each positions. You can ask what their ultimate goal is in their fields, ask them why they decided to leave their last job. Most importantly, see if they are compatible with your personality.
Something obvious I didn't understand at first: the earlier stage you are, the smarter the people you need.
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.