Hiring · Startups

Would you hire a CTO that’s never worked at a startup?


August 14th, 2015

If the CTO came from a huge tech company and had never worked for anyone else, would you still consider hiring them in that sort of leadership position at your startup?

Karen Leventhal

August 14th, 2015

I can't speak about hiring but when I "interviewed" folks as technical co founders, who had never worked at a start up... maybe they worked in large corporations, maybe they worked in mid size software firms, but invariably they would be very interested, and want the title and the equity, but then weeks or months into discussions they would reveal the expectation that they were going to be paid a full time, full scale salary within a month or two launch after launch, even though I had been fairly clear about what the work entailed at the beginning. I think they just thought I was negotiating,  not that this is actually the expectation in a start up.  It just seemed to be a common disconnect.  That's just my anecdotal experience. 


August 14th, 2015

While I'm not a fan of absolutes, I'd avoid this if possible, David.  Particularly at the earliest stages, you'll get odd looks from them about things that are very typical in a startup.  We had to part ways with a CTO (non founder) at my first company after he insisted that we weren't respecting his space by even emailing him on a Sunday.  Amazing engineer M-F, but you need something different at the early stage, IMO, and that includes a different level of obsession, flexibility, ownership, independence, etc. My two cents....

Richard Lindenmuth Verto Partners Founder - Interim CEO at Styrotek

August 14th, 2015

People frequently ask what is the difference when I work at a $1 Billion company or a start-up. My comment usually is that at the $1B company when we have an issue, opportunity, project I look around and select a team to put it together. At a start-up I look at the "other" two team mates and say "Ok, whose turn is it". People who do not have the experience of doing it themselves do not do well in start-ups

Taj Sateesh CEO at Sphinx Resources--The Preferred Recruitment Partners in Hi-Technology R&D & Manufacturing

August 14th, 2015

Maybe as a consultant/advisor...Yes...David.
But not as a hire.
Guys from large corporations sure have a lot of stuff that would be useful to any Startup.......but @ later stages during the process of scaling-up. The mental attitude & frame of mind that's needed in the initial stages is lot different from what's needed later.....one of the reasons why startups go to hire guys from large Companies who have handled scaled-up operations when they reach that stage.

Like Richard mentioned, in general, most people get tuned/used to the various systems & processes wherever they work for long durations.....which could include a secretary, a team from whom he/she can make a choice, coffee breaks, perks, etc, etc
When one talks of a startup in the initial stages, all these choices/facilities would be missing for sure & to top the situation--where the person COULD find tough to adjust--would be the situations of untimely food, no-weekends, long hours, limited family life & so on. Essentially, a serious culture fitment issue.
In such a scenario, the person would SURELY benefit & learn about working in startups.......but @ YOUR cost.
In short, the hiree would gain far more than you when you hire him/her in the initial stages of the startup.


Glenn Donovan Vice President of Sales (fractional)

August 14th, 2015

I'm intuitive about hiring and promoting and while I think all the above advice is sound, my approach is to trust my gut (which has been wrong sometimes). In this case, the lack of startup experience gives me more pause than the management experience. But I also try to see people on a trajectory versus in a static place. Oftentimes a new role that offers growth and better potential to someone who is "stretching" towards that new role will motivate an individual to amazing feats and commitment.

But in the end, I also think hiring cold is a crapshoot - I know, that sound awful but in my experience if you don't know someone, it takes 3-4 months on the job before they let their hair down and you see who they really are. This is why I almost always recommend founders know each other well or at least come out of a trusted network where people who know you well and that you trust can vouch for them.

Juan Zarco Managing Director, Silicon Valley Ventures Growth Partners llp

August 14th, 2015

First, I would find out whether that technical guy had managerial roles in his previous position. Second, as someone commented, such person needs to have the right mindset for working in a startup environment with strict deadlines and long hours. Third, the CTO role is a supervisory role that covers various technologies and expertise. If this particulary guy has a very narrow expertise, can that person manage others as well?

Chris Kitze CEO at Safe Cash Payment Technologies, Inc.

August 15th, 2015

A raw start up will need someone who is experienced with the chaos of a startup and for that reason, "big company people" are probably not a good fit.   By definition, they chose a path of comfort and certainty when they went to the big company with a steady paycheck and where that enterprise removes the risk.   A startup is the opposite of comfort -- you are on a path on the edge of uncertainty.  Startup people are uncomfortable with certainty.  If you are doing a start up and everything seems certain, that's the time to worry.

A startup is a different beast -- two days are a trend and you have to constantly adjust everything.  You might even discover there's no business at all!

Only bring someone from a larger company background post Series A once the core business model has been established and you have funding.  Too many things are moving around and they won't be able to handle it, it's too far outside their realm of mind and you'll spend half your time trying to keep them from quitting.

Glenn Donovan Vice President of Sales (fractional)

August 26th, 2015

@Patrick McGuiness - "Experience is overrated. Skills are underrated." - Quote of the thread.

Having worked intimately with 23 startups, I find the doctrinaire answers here quite small minded. I also want to point out that one learns some very good things working for a large scale company that are quite useful. The din and hum of a large corporation demand that one prioritize and focus on what's important if you want to be effective. You also have resources to do interesting projects where you might learn things which apply universally. You may also get to see a wide variety of projects and challenges that a startup will never see, all rounding one out as a business person.nOf course, it goes without saying that many people cannot make the transition, but to categorically claim that such a person couldn't be a great contributor to a startup? Nonsense - it happens every day.

@ Peter Johnston - Gosh, I guess I'll go tell that founder I'm working with who had his entire app - from front to back end - developed by an outsourced app dev shop that he did the impossible. But gosh, he already has 6 Fortune 500 pilots - paid pilots at good revenue - and over 10,000 users. He's only now looking for a CTO..

I normally enjoy your commentary but I find your thinking here to be very hard to relate to. One thing you said really sticks out. You claim that the only innovation opportunities that exist are due to technical innovation, and this argues for a technically led company. Really? Two problems. First you assume only technical people can see those business opportunities, when in fact one does not have to be a developer to apply technology in innovative ways. Second, you assume that technical people can actually capitalize on those opportunities - having only a technical background. Both simply are not true - the world proves this every day. In fact, I find that many technically focused people have terrible business and strategic sense - and why wouln't they? Others have worried how to pay the bills and build a business while they coded.

I think this reflects the 'Y-Combinator' effect, they only fund startups with young technical founders, lol. I guess if wearing skinny jeans and having cool stickers on your laptop is now an indicator of skill, well good luck with that. I'll stick with good strategy, a good market opportunity and good leadership. Technical skills are widely available and are not the end all, be all of building a successful technology based startup.

Patrick McGuinness VP of Engineering, CTO, Software dev mgr, & Entrepreneur/Founder

August 25th, 2015

As someone who came from a big company to a startup CTO role, let me share a different view and perspective. You should hire based on skills and passion, not experience, and so the question is the wrong one. The best answer thus far is "it is completely contextual". The candidate may or may not bring the skills you need, but that experience won't be a big predictor. It both helps and hurts to have that frankly.

I spent 20 prior years in big company software development, management etc., but also before signing on as a startup CTO was doing my own startup efforts. I did indeed have to shed many habits and patterns, and if they have a 'big company mindset' that's a red flag, but the other side of that is that there is a wealth of project and leadership experience that can be useful from someone who's done or led larger projects, even if you have a team of 2 to 4. (e.g. I can check off the 'working with offshore developers' box, did it for many years.) The context for me was I was willing and able to jump in and do the role I was hired for, was hands-on and was v different from my earlier management roles. There is a culture shock / difference to go through, but I embraced it.

Experience is overrated. Skills are underrated. It's funny that big companies tend to hire based on experience, and yet many startups manage to suceed by breaking those rules, but lots of answers above seem to preclude the possibility that someone might make the jump from one type of company to another. The plain fact is that if you had plenty of money, you too could do the safest thing and hire as CTO someone who did it before successfully - but then if you are a *-strapped startup, you might not afford that or have that oppty.

Should you hire someone over 40? should you hire someone or a different ethnic background? That's the wrong type of question. Any decision based on a bias like that will be in error. Likewise, being in a big company should be no bar, but whether it is an asset depends on what the person had done and what they can do for you. Better question - ask if this candidate:
1. Has the *desire* to be in a startup environment vs big company perks and limitations. Ask them why they want to do the job. Ask them indirectly, again, and dig in to whether they have the passion to live with chaos and doing more on less.
2. Has the hands-on skills to be a direct contributor. Early startups should have 0 'managers' (Mark Cuban rule that all directly contribute), non-contributor managers are dead weight. Ask them to visualize their daily routine and their main goals/activities. Vagueness or mumbo jumbo is bad/ red flag.
3. do they have flexibility, collaboration, and pro-activeness. Don't tell me where they worked before, find out what they've done and can do in a fast environment.
4. The job is to turn the vision into a product reality - whatever it takes. So they need to have vision about the product and the process, have both the big picture and take care of details. Too many big company people are order-takers, you need a *leader* who cares about the product enough to be thinking about it 24/7. If they dont have that mindset (ie 9-5 mindset), take a pass.

Tim Scott

August 14th, 2015

Think of it this way. You're crossing the Rocky Mountains on foot. You might prefer that someone on your expedition has made the attempt before. That is to say, if you have no startup experience, you might place a premium on attracting another leader who does.

That's easy to say, but do you really have that choice? You might face a bootstrap problem. An experienced CTO will be looking for an equally (or more) experienced biz founder. In the current market, they're likely to find it. To overcome this you probably need to be exceptionally dynamic and/or show plenty of traction.

Everyone has his/her first rodeo. You might find a great tech leader from Big Company. While there are certainly job-specific advantages from prior startup experience, it's probably less important for the tech founder than the business founder. The bigger issue is, the average techie is less likely to have the personality traits a startup requires. Spend as much time as you can getting to know him/her. Probe for the qualities that large companies tend to squash like flexibility, creativity, thrift, work ethic, business IQ, etc.