Ask HN: Should I accept a CTO position without much experience?

I mean, for me personally if I were interviewing there for a staff engineering position and I found out that they'd taken somebody with very little professional experience as an engineer, along with zero executive/leadership experience (director, VP, GM, etc.), and then made them CTO... I'd wonder what was wrong with the rest of the company leadership.

For reasons not the least of which are... when you go seek funding any half-way legitimate investor is almost certainly going to look at the leadership team, its prior experience, its successes, its failures, etc. Unless the thing you guys are doing is the world's most amazing product that's hyper defensible and hyper differentiated, then a huge component of what the investors are evaluating isn't the business or the product... it's the team.

But all that said, you'd learn a whole crapload from the experience, so perhaps it's best just to have at it.

About the only other thing I can say is... if you're having to ask this question in a public forum on the internet to a bunch of strangers, then that's probably a pretty useful indicator of your actual preparedness in and of itself.

Your success as CTO is mostly determined by yourself. Understand what's required of you. Start interviewing other CTOs at other startups and understand what their roles are and what they need to do. Build relationships with them so that you have a network of advisors if you ever need someone to have a chat with. Learn a lot. Do a lot of research. Do a lot of thinking.

Leadership is not all about experience. Leadership is also about listening. And all leaders start from somewhere. Once you have an open mind to learn, you'll realize that being a leader is about being courageous and responsible for the happiness of other people. It's also about helping to steer the ship in the right direction. But with all startups, you're making decisions on minimal information. What you need is a mind of learning. Test and learn and never assume you know it all. Then you'll be fine.

The salary issue is another big issue. Would it be worth to trade away your salary for the experience that you get? How will you survive? Do you have enough savings? Do you have a backup plan? If you're not getting any salary, then you should get significant amount of equity. And at this stage, as the CTO, will you also have to build the product? Job titles at early stage don't matter much.

Lastly, do you trust your boss enough that he will steer the ship correctly? Do you think he has what it takes to make it all work? And how is your relationship with him? Will he listen to your opinions or is he going to make all the decisions by himself?

Good luck

'Until we get funded' translates into 'unfunded', and 'could be in May 2016 or even before that' translates into 'possibly never'.

If you don't have money in the bank and if you can't sit this out for a year or more and walk away without any scratches then I would strongly advise against taking this position, but be sure to thank them for the compliment. Join a start-up that is already funded instead, maybe not as the CTO but at least in a position where you can pick up the skills that you need.

Also, if you do take the position consider the very real possibility that you'll be ditched as soon as they can afford someone more experienced than an intern.

  > I really was looking for a stable job
  > just to get more experience
  > save some money and
  > eventually become an entrepreneur and create my own company.

Either way you can still pursue your own business(es) in future.

If you're going to work for this startup for no salary, you need to ensure that the rest of the deal is fair.

i'm somewhat jaded, so i'd suggest reading this: https://michaelochurch.wordpress.com/2012/07/08/dont-waste-y...

My biggest concern would be your boss(s). Do they joke about doing shady things before or in the future? Do they do drugs? Are they pathologically unable to talk about anything other than how much money this app/idea/business will make? Do they occasionally do dumb things like fund the start of the company by giving away 55% of the company in exchange for $300,000 from their soon the be ex-wife and her friends?

I second this. I have no way of evaluating the character of your boss, but there are warning signs all over the place.

My story: I was hired to build a MVP (did -eventually- get paid) and due to various missteps, it turned into a one man job (I was the entire IT staff for 4 years). Part of those missteps were me being work-obsessed (a bad trap to fall into, it leads to burnout) and the other misstep was that these founders, who had no experience in IT, were all psychopaths (as in one had a criminal history of fraud, the other should have been jailed long ago). I failed to do one of the basic tasks of business, which is know who you are dealing with.

They used my "enthusiasm" which in the IT/startup world is quite necessary, and leveraged it against me. I certainly knew enough at that point in my career, but it got lost in the need to keep things working. Eventually I wised up, when a customer made legal threats because they had been blatantly lied to about the product they were buying.

I, as <u>nominal CTO</u>, had not been paying attention to the sales process and stupidly was relying on the others to take care of that area. It was then I realized the full nature of the whole operation and how I'd been taken advantage of - so I quit. I reasoned they were going to fuck me over one way or another down the line, so I'd better get out.

Less than a year later, the CEO abandoned his wife and kids <as in literally disappearing one day> (she owned 51% of the company) and now they are still fighting it out in divorce court. The CEO turned out to have a 25 year history of fraud and cheating even the companies he worked for.

So ... the people you are dealing with --may be-- great, but you have no real world experience in how businesses are run or how life actually is at the C layer. Read up on the Sociopaths/Clueless/Losers theory - it is a valuable thing to know, as it explains a lot. I've seen shades of it over my 30 year career in IT, but it never hit home till I did this startup.

And if you are really CTO, and a salary of $0 is being offered, why have you not mentioned the percentage of equity offered? If you really are going to be responsible for hiring and designing the tech side of the company and ... you should be getting a large chunk of the company. It is irrelevant the company already exists - by being an official CTO, you are taking on a lot of responsibility.

No offense intended, I'm sure you're capable of programming and all that, but ... I wouldn't hire a 24 year old with just a few years experience as CTO. The Master's is irrelevant in this situation - there is a lot of non-IT social type knowledge needed, IMO. The politics of business is nasty stuff, and your stereotypical engineer (i.e. me) likes to stay out of that stuff; it is a skill set you have to either like (and so you're an asshole) or you just get used to it. I've always tried to stay out of it, hence the 15 year career of contracting.

I think my advice is, if you want to stay with this company, then say you want to be "Lead Architect" and leave the management/business stuff to someone else - then you can expect to get a salary and will only be tangentially exposed to the business/political crap that typically goes on - that way, you get some valuable non-IT experience safely and some tech experience too. When (not if, this all doesn't sound like a winner) the company crash and burns, you'll have some useful profit out of it.

Yes accept! Use that fear of failure to tap into your drive, creativity, and bring your A game. Business/Tech Management/Leadership are ALL learned and practiced things.

Money should NOT be an issue-- go to back to your boss. Share with him your bare bones monthly budget. Tell him you need $X just to eat beans & rice and pay basic bills. Can he help cover you during the gap before funding? Could someone else, say a family member cover you for 6 months? Strike a bargain with him, keep your part-time job for necessary cash-flow, then work part-time on the startup. If you believe in this guy, the two of you can find a way.

Incidentally, you might find Josh Kaufmann's Personal MBA a helpful read > https://personalmba.com/

I'm facing the tough decision of whether or not to jump ship.

Btw, are you in the US?

Where can I find people like you who will work for free on the promise of future money dependent on a roll of the die which is funding? Please tell me. I'll take one CTO, 2 senior devs, and 4 junior devs.

Here's the deal. I don't know your situation, but you are basically saying that your time is worth $0. That might be true or it might not be. You have to be the one to decide that.

Additionally, if the company gets funded, the very first thing that will happen is you will be fired or otherwise relieved of your position and they will hire an experienced CTO who will be paid a lot of money. This is the smart money move for them and a pat on the back for a job well done is all you will be likely to get. By that time, you will have no solid programming experience, having played spreadsheet warrior for a year or two, and being at least one level abstracted away from the real work through which you would earn your bread once you leave this losing lottery ticket.

Finally, you have no experience. You might not even conceive of what this role requires. You are being asked to be a CTO during an internship. This is a glorious chance to fail. How strong are you emotionally, to face a humiliating failure? Your decisions will be picked apart and your current lack of experience will be laid bare for everyone to witness.

And yeah, we failed, like most startups do, and I had to quickly scuttle to find another source of income. That sucked. Truth be told, I'm still paying off a lot of debts I made from trying to survive sans-salary.

But I have no regrets whatsoever about what I did. It didn't make me a better programmer, but it did make me better at helping employees out, it made me better at understanding productivity, and it gave me an overall better perspective on how to build great products.

And don't worry about engineers being smarter than you. Doesn't matter, that's the ideal anyway. The important thing is to be the one who listens and makes things better for the engineers so they have what they need to build a great product.

The salary part sucks, yeah. I basically had to moonlight when I was working as a CTO. This is where I would really advise you put some serious thought as to whether or not you would really be committed to this startup, because in all likelihood you'll wind up with a full-time-plus job as an underpaid executive, and you'll have to moonlight on the side in order to make up for the remainder of the unpaid bills. You won't have a whole lot of time for side-projects, if any at all. Not for a while anyway.

But seriously, don't worry about failure. As long as you listen you should be okay. Even if you're not, you'll still learn something, and it'll be really valuable for the next phase of your life. Case in point: I'm building my own startup now, and I have more confidence going into it because of the lessons I learned.

Oh, and one more final takeaway. You'll have to do some fighting. Your job as CTO of is to lead the technical element of the company, but fellow executives, or your boss, may occasionally step on your toes. Sometimes they're right, sometimes they're wrong. When they're wrong, stand up for yourself, be diplomatic about it, but don't be a pushover about it, and back up your case with some evidence. You'll win some and lose some, just try not to lose too many crucial battles.

2. The idea of hiring people smarter is sound and will server you and employers well. Employers are people who actually pay.

3. If funding is as far away as May, the company is underfunded and has difficulty raising capital since it needs capital to pay your salary now. Or maybe the boss plans on replacing an inexperienced CTO with an experienced one once funding is in place...my friend Greg once got hired with no professional experience as the chef for a restaurant a month before it opened. I went to the grand opening party on a Thursday night. Friday there was a new experienced chef and Greg was out of a job. Clearly, none of that was spur of the moment.

4. If the title on your resume seems more valuable than knowledge skills abilities and money, then strongly consider the offer.

Good luck.

Lesson #1: Trust yourself to make the right decision to move you forward.

One thing I'd like to add, assuming the financials work out and everyone is happy, is that moving from CS/programming to a CTO position is going to require quite a different skillset. You probably won't be programming all the time, at least not after whatever project they have in mind is in a stable place. You will potentially be responsible for reporting/BI/analytics, systems architecture and administration, tech support (Yes, everyone is going to ask you for help with their computers), and anything else tech-related that comes up along the way. If you want to stay in good shape as a programmer, you'll be responsible to find the focused time to code, keeping your skills sharp and current, and staying motivated to do so. At this time, you'd normally go work with an established development team who can guide and mentor you, as well as balance the team so that you have time and resources with which to further your skills.

The only thing in your post that makes me think this may be a good opportunity to explore is when you mention entrepreneurship as your long-term goal. This is likely going to be a great crash-course in how difficult that can be. My advice, though, would be to get great at what you know and learned, spend a couple years on a great dev team, save some money, and I bet there will still be opportunities for you to get into a startup for all or mostly equity.

Hope this helps. I'm just a young guy who's seen some different sides of the equation.

If for some reason you really believe in this company and team and are willing to go without pay, you need to be a cofounder with 10-20+ percent of the company (depending on the number of founders). You are the only technical person and they need you enough to make you CTO.

Anything less and you should run. If they do get funding, as others have said, expect to be replaced, possibly prior to vesting whatever stock you did get. You need a large percent ownership and a single trigger acceleration clause in your contract so you get your stock when they fire you for no reason. [1] Even then you can get diluted to nothing, but with a large percent ownership and accelerated vesting it will be more challenging.

You better really trust these people, believe in the mission, and get a large percent ownership with the right contract. Any hiccups or hesitation from them and you should walk, unless you want to learn first hand the dark side of startup bullshit where you gamble with no pay to make other people rich.

[1] https://www.quora.com/What-is-the-difference-between-single-...

This should trump everything else. Don't listen to excuses, don't believe that "it's a great opportunity for a young person," that "it will enhance your resume," that you will "gain valuable experience."

Do. Not. Work. For. Free.

Once your boss agrees to pay you market salary at least at the junior developer rate, then you can get into your lack of experience and whether or not it's a good idea for you to be CTO (hint: if you're asking, then it's not). But,

Do Not Work For Free.

Was your internship unpaid?

But it means absolutely that you become a cofounder (> 10% equity). Anything less and you're getting played.

I agree what others have written so I'll just add this. In my experience, you'll be happier following your own path rather than waking up one day and realising you've been following someone else's path. If that's what you're really looking for, then that should be a strong indication of what to do.

you: 0 $us until we get funded... save some money and eventually become an entrepreneur.

If you accept a major role in a society, conscious of losing money and time, and you're willing to use your savings in the hope that your work will bring results within a specific time ...

Wiktionary->entrepreneur: A person who organizes and operates a business venture and assumes much of the associated risk..

you: And apparently, they saw my "enthusiasm" me: if you're willing to work for free between now and May, the enthusiasm is not the first thing that they noticed.

Should I accept a CTO position without much experience?

my answer is Yes! but prepare yourself to an experience that will make you grow up in many different ways ...

That being said these are the considerations that were in my mind when I was in a similar position.

1. Just like an investor or even more so, how much do I believe in the founder. 2. How confident are you in your abilities. Are you able to cope with stress/uncertainty and preserver in the face of daunting tasks. 3. How much do you believe that there is a business somewhere in there?

If you are enthusiastic about all 3 the risk is worth it. Feat and doubt are poor reasons to not do something. Fear is a good sign to pause and evaluate the situation. There is only one way to find out if you have what it takes. Also if you think taking a low income (or no income) is a big issue now. It only gets harder as you get older. Wife, kids, mortgage and general lifestyle inflation.

Are you really willing to toil away without any income while he sits there comfortably, scheming away, trying to figure out the next best way to rip you off?

Please, don't be afraid to say no to this terrible offer.