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Which type of CTO best worked for you?

A detailed account of a Fastlane process...

Choosing the CTO: which guy/gal would you pick?


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    4

QueenVictoria

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Aug 27, 2014
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Let's say you have a start-up and you're choosing the CTO.

In your experience, did you prefer the younger, just graduated guy/gal with the M.S. degree- who is quick and adaptable, who can find innovative solutions to challenges, but lacks managerial experience or

The seasoned guy who's been a CTO of a few companies already and requires a mid-6 figure salary? Is the experienced guy worth it?

Or would you roll with the junior guy who's going to be shaping the company but lacks managerial experience?
 
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MarkNNelson

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Current undergrad and grad-level work in CS is somewhere between useless and really useless. I would say the MS means nothing in your situation, plus or minus.

If the seasoned guy is seasoned in current tech, and by startup you're talking about like a 20-person deal, then it might be worth a shot.

BUT...

If by startup, you mean folding tables for desks, everybody crammed in one room, 5 employees, then no, not the senior guy. He can't hang in that scene.

You want someone who currently writes code (code code, not someone who says they know Wordpress or CSS). Find someone who can admin a server, who contributes to GitHub, someone who gets shit done. The management piece can come later. The person you need in a 5-person startup is different from who you need at 15 or 20.
 

garysvpa

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Let's say you have a start-up and you're choosing the CTO.

In your experience, did you prefer the younger, just graduated guy/gal with the M.S. degree- who is quick and adaptable, who can find innovative solutions to challenges, but lacks managerial experience or

The seasoned guy who's been a CTO of a few companies already and requires a mid-6 figure salary? Is the experienced guy worth it?

Or would you roll with the junior guy who's going to be shaping the company but lacks managerial experience?


The experienced guy...

A CTO to me is a leader, manager, colleague and technologist all in one.

He will never say "that's impossible" or "we'd never do that."

He will always find ways...
 

Nate-NewVenture

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When it comes to the Chiefs of companies, I think the experience outweighs the innovation. A person with a proven track record for results (a leader) is what you want in a top tier exec. The reason why he/she has employees is to prove the new, innovative tech that has the potential to change things for the better. They "pitch" their ideas and the executive vets out the ideas based of potential for success/failure, if it aligns with the path of the company, and what the risks (technologically and financially) are. That is where experience comes in. He/she needs to know exactly who is working for him/her and determine if the idea can be attained with existing staff or additional assets are needed.

Make sense?

\000/,
Nate-NewVenture
 
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QueenVictoria

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Aug 27, 2014
33
16
When it comes to the Chiefs of companies, I think the experience outweighs the innovation. A person with a proven track record for results (a leader) is what you want in a top tier exec. The reason why he/she has employees is to prove the new, innovative tech that has the potential to change things for the better. They "pitch" their ideas and the executive vets out the ideas based of potential for success/failure, if it aligns with the path of the company, and what the risks (technologically and financially) are. That is where experience comes in. He/she needs to know exactly who is working for him/her and determine if the idea can be attained with existing staff or additional assets are needed.

Make sense?

\000/,
Nate-NewVenture

Thanks for your perspective. I'm wondering who some of your favorite C-level executives are? And if your opinion is based on ideology or if this is something you have witnessed within the start-up community?
 

The-J

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If you can afford the seasoned guy, take him.
 

Nate-NewVenture

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QueenVictoria,

I've got some rather famous CEO's and some not so much. I've been fortunate to work with several that I could directly interact with.

First off is Steve Jobs (obviously). His tactics was rough around the edges at times but if you read his book and try to understand his thought process, you'd discover that he was doing what we're all trying to do: Fill a Hole. He had the vision of what people wanted, not needed, wanted. He genuinely cared about that vision and was unmoving (to a fault) about getting what he most cared about: solutions.

Secondly is a not-so-famous guy named Harel Kodesh. I worked with him when he was CEO of Wingcast, LLC (A Ford & Qualcomm company). While there, I was a worker drone and had a burning to do more. I got a chance to have several meetings with him and found that he, too, had an eye for the "holes" and solutions. His process was more salesman-like in that he could schmooze his way into any situation. Is that a bad thing? Absolutely not. Getting through the door, sometimes, is the easiest part. Staying in the room is where the challenge begins.

I have more but this would be a long reply. Bottom line is, if you look at all your "idols", so to speak, it really shows a lot about you. You wouldn't idolize someone that washes cars all day but you would idolize someone that you feel shares the same values and has something you don't currently posses. Ask yourself, why you don't have it. Don't make excuses, genuinely ask. I did. It is changing my life daily.

Just my 2 cents,
Nate-NewVenture

Thanks for your perspective. I'm wondering who some of your favorite C-level executives are? And if your opinion is based on ideology or if this is something you have witnessed within the start-up community?
 

RogueInnovation

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Hire slow, fire fast.
Hire really slow, fire very rarely.
Hire really slow, and use your talent across your businesses like branson and you can create a loyal workforce with great job security that "get" and "cherish" the company culture.

I think the first port of call for hiring anyone is WALK rather than talk.
When you get started, you over promise and underdeliver, and it sucks, but as you develop your skills you will start to be able to under promise and over deliver, which is great.

To secure a persons job, requires you to be in touch with the relevance of their job in more than general terms, but rather, extremely specific terms or they'll be threatened at losing their job from word go because you are asking them (the employee) to take on the pioneering and uncertainty, YOU as the entreprenuer must burden.

Employees should come in the wake of your success to help automate a system you know works, and can dumb down for them so they can do it just as well as you, they shouldn't be the plow or bullbar, that take the brunt of the business uncertainty (if they do, they probably deserve equity, not a salary).

Hiring to me, comes in three stages.
Casual/Startup - Everyone is eating ramen noodles and bootstrapped, the costs and expences are kept super low and, the profits are divided into expences
Automated positions - Say there is a repetitive job that is taking up all your time but is connected to a revenue stream directly, such as mailing off all the products, or doing the sales phone calls, or creating the content that drives in traffic, you hire these guys on contract.
Commissions, rewards, full time - You start to get in the flow of the business and not a lot changes, so you want to keep people happy and give them great jobs, you then give full time positions and all the perks you like, and set up an infrastructure.

You won't be able to create secure positions in your company while starting up because the business functions like an archway, the market supporting you, and you supporting the market, and if you hit bumps, everything can drop back to square one until you get all the things to "gel" just right. Once they gel, you can start to be more confident in who you hire and why.


Just starting up, you shouldnt hire a "cto", what you should do is ask the question, WHAT IS IT THAT WE REALLY NEED TO ACHIEVE, you'll be surprised how knowing what you need makes a lot of positions and jobs obsolete. You start off thinking you need a full time sales force but then you only need a guy coming in now and then, and no matter how much you want to pay him more, it just makes no effect on the profit of the business, so you will be forced to cut back.

Some bigger named entreprenuers now push these employees into several businesses, or rotate employees between different jobs, because this way they can give "full time" positions, and fulfil multiple casual positions etc. And it is in this way, the future is going regarding helping cut back on the layoff culture.


Anyways, business is like a snowball, that keeps breaking as it rolls down the hill... The tasks get condenced as you better understand your business. If you don't plan fluidly, then you will always create redundant tasks, and the business will suffer. Hire at the start, people that are the most flexible, not the most perfect, so you can prototype and set up your ideal routines, and then from there bring in talent.


A lot of software companies in silicon valley try to attract talent by making their company culture the coolest, so snack bars, great lounges, sleep breaks, a vibrant atmosphere, and in this way attract people to the life style, and pay them well.

But in the end, people gravitate towards success. People go to google, or to facebook etc because they hope that success rubs off on them and can help them towards their dreams. So the best way to attract talent is to be seen as the cutting edge, as the new guys in town who could do great things and who are getting a reputation for stellar work. People in that case want to get on board and prove themselves in that testing ground, and thats how you attract them.

But perhaps more important than that is networking, starting to talk to developers and not just for job positions but regarding all kinds of things, learning to be a leader, learning to relate to what they are best at. It is this way you will meet people you can employ and keep onboard for the longer haul.


You cant hand out jobs though, you have to build them first. And to do that is always a knifes edge, always dependant on how soundly and diligently you have run through your business.
Once you are a CEO that truly and consistently brings in business, your views will have evolved and developed nuances in understanding the positions you need, and you'll be able to strategise how it is best to be generous to your workers and BE EFFECTIVE.

The problem with assuming people just need money, and jobs, is that you overlook what people REALLY need. Which is hope, understanding, empathy, flexibility, support, loyalty. You might find that commissions are best for your employees performance, but that a wage set as a safety net at a certain level helps them feel appreciated.

But in all honesty, employees might not be saints, and while you may do all these good things for them, there is no garuntee it is going to help them. In this case you might find that something other than money will REWARD them and support them better.


Thats the problem with creating a business off ideals, rather than, scrutinising every aspect as you go, all the time, every day, because if you set your ideals, you probably wont pay attention to the opportunities all around you to create efficiency and well being for those following your lead.

IMO, I can't promise jobs. I'd LOVE to, but I'm not a good enough businessman yet. So I do WHAT I CAN, and what makes sense, for the context I am in.


If you are a startup, don't start out hiring on a salary as its capital intensive and highly inflexible, instead, ASK people what they need to get on board, involve them in your brand, your ideals, and the hopes. And you may find close companions for that journey willing to take those risks with you, BEFORE you can promise them a penthouse apartment and a retirement fund.

You have to GET to your goals first. If your goal is to reach the stage of credibility and financial stability to afford a secure position for a very talented CTO, then ok, but you have to then ask, how are we going to get to a stage where we have X customers, supporting that. You have to ask, is it right for the company, is it necessary, or is it vanity???



You ever watch shark tank or dragons den and see the business school graduate come in and bravely stand up to the investors, only to get yelled at and shot down cuz they havent thought of the actual business. Well, thats something to avoid. You want to soften up your business attitude and look towards realism, creative solutions and knowing how to support each action you make.

The more you develop the roots of your business, the more likely the tree will recover from the storms that will come in.

Business is as much spiritual as it is intellectual, and you have to become this consistent check and rechecker of how crucial things are and how they should be adjusted to get in sync with opportunity.
You have to really start to gain a passion for it, develop a steady process, and with that productivity, and you making the right profits etc, slowly and organically build up all the minutia that will be crucial for success.


When that happens, you CAST OUT your tentacles, or your mind, and you develop what rocks for all your employeeds by squeezing value out of all the little details you understand about each specific goal and how to optimally deliver good stuff for everyone.


You have to develop a sense first.
I'd recommend that if your company is very tech heavy, you network, see if anyone cool can express your ideas for you and that you spend a lot of time getting your company to profit so you can hire him.
You cant do that right away, and thats best case scenario, worst case scenario, everyone ignores you and nobody can express your idea and you get no sales!!!
In that case you have to find a way to success outside of the obvious, and find a miracle.

Success storys are very rarely, point A to point B, you have to go through the cloud first



The best way to get through the cloud is to brainstorm daily and scrape up the best and slowly sculpt something good from the best.



TEST and SCALE is the formula for business, testing requires loads of failures, and loads of reiteration, until things start to click, and then as you understand and simplify the success formula you find in that cloud, you then simplify it, and start to scale it. You don't just blow it up, you like walking a tightrope or a cliff edge, test the water first and then you slowly make your way ahead.

Don't sail at full sail in rocky waters!!! Its not necessary and dangerous! Slow down, sail at half sail, and carefully look for the rocks.

Startups are NEVER smooth sailing. So don't sprint, just crawl, and plan, and replan, and try to get real indicators of success on your side, profit being the most important one, a functioning model, second.

TL;DR
 
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