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Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @09:39AM (#11893742)
tl;dr: in your situation many people go off and get an MBA. Don't do that. There's a reason there's only one CTO in HBS' 60,000 person alumni database (I am she.)

I was a very hands-on CTO for years after a decade of coding, and broadly enjoyed it. But as the teams I managed grew it became increasingly unfulfilling. When you're CTO, you're often excluded from business decisions which have a bigger impact on your team than any tech innovation, and the input you do have can be hard to relate to the shared business context of the CEO/COO/CFO.

So I went and got an MBA (Harvard).

Now I know exactly how to frame (and improve!) my non-technical contributions, have much more context on what "success" means, and have the credibility to really be a part of the senior team.

Unfortunately, there's no real place in the world for a highly technical business leader. You have to leave code behind at a certain point and spend your time on people/financial/planning issues. The ultimate end of that road is CEO, and not everyone wants to go there.

Also, I'd really misdiagnosed my malaise. What I'd been missing was not strategic input, but the opportunity to build things. To weave together inspiration and ideas into innovation and growth. I love building things and challenging assumptions, it fulfills me.

Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Re:Ask HN: I don't enjoy being a CTO. Now what? by sailfast on Monday June 13, 2016 @10:06AM (#11893965)
> Unfortunately, there's no real place in the world for a highly technical business leader.

While I certainly see evidence of this in the workplace, I also see that this kind of leader would be exceptionally valuable to any organization. Do you find that the issue here is that companies already at scale have separated concerns so highly that the management skills are more valued (so technical leaders go to startups / smaller places) or is this really just because us technical people like to build things more than manage things?

This is super interesting input - I think that on this answer, depends a lot of the future of companies, but also where technical folks can and should target. (Although you mention CEO which, I mean, that's a leadership role too hehe)

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @10:25AM (#11894121)
> While I certainly see evidence of this in the workplace, I also see that this kind of leader would be exceptionally valuable to any organization.

You'd think!!

I have a few theories as to why this is so:

The most charitable interpretation is that, since technically competent business leaders are so incredibly rare (set aside that every engineer thinks they can do it), there's no design pattern for that leader. Ownership is ritually divided into COO/CTO/CFO, and of those CTO is linearly defined. Technical leaders are excluded from non-technical discussions by default, and norms are extremely hard to break.

^ This is why I recommend against great Engineers doing an MBA. There's just no role at Amazon/Google/etc. for that profile beneath the VP level, reporting trees for engineers/business branch at the second tier and never meet thereafter.

A different perspective is that in a sufficiently technical organization (ie: everyone, these days), technology is a giant black box to the rest of the leadership team. It's a big part of the budget and a massive component of success, yet completely opaque and unfamiliar to someone who rose up through sales/marketing/etc. In their minds, the CTO already has an outsize impact, and surrendering to them more scope is scary.

Re:Ask HN: I don't enjoy being a CTO. Now what? by tamana on Monday June 13, 2016 @10:51AM (#11894297)
Why would a techie want a MBA job below VP level? Most don't want to be advertising account managers or business analysts either. Does that matter?
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @11:07AM (#11894433)
tl;dr: If there's no reason to get an MBA as a promotion-track engineer, then not only will none of your promoted engineers will have MBAs, none of your promoted MBAs will have practical experience being a great engineer.

They wouldn't, of course. And that's really the problem.

If you don't have mid-level technical managers with MBAs, you don't get to promote/hire VP-level technical MBAs.

An MBA does teach a lot of valuable skills. As many smart technical founders/leaders have crashed up against the corporate rocks of running a major division/initiative as business leaders failed due to distance from execution.

Right now though there's no role, and no opportunity, for a mid-tier (post-MBA) capital-E engineer. So there will be no MBA-toting, engineering-aware VPs.

Without business-fluent engineers (or engineering-fluent business folks) companies are deprived of interdisciplinary innovation. You get financial programs which ignore technical needs, and great inventions which don't have a market. Promotion which doesn't represent reality and deals which can't be executed.

Most of the frustration engineers have with business people is not that business folks can't do business well, but that they don't do so understanding the underlying technology.

And until there's a reason to want a techie MBA (or business-y Eng) at a sub-VP level, this isn't going to get better.

Re:Ask HN: I don't enjoy being a CTO. Now what? by nekopa on Monday June 13, 2016 @11:51AM (#11894835)
So why don't we, as an industry, talk to the Universities, and say that we really need a new program, let's say a TechMBA? (Or for marketing purposes, call it a TeMBA - that really rolls off the tongue :)

I'd think that there would be some interest around this from the universities, and business is really crying out for this too.

From the Uni viewpoint, it is another product they can leverage, whilst still using there in house competencies and also creating cross university synergies (HBS-MIT TeMBA)

For businesses, they get exactly the top management they need - even for non-tech companies - a CIO/CTO with solid tech skills and business skills is a sure winner.

P.S. Please forgive me for slipping in the word synergy. I truly believe it's a great word, with a great meaning, but has been flogged to death by the consulting industry.

{Edit} Actually, I like the idea of a TeMBA, I am going to start a AskHN: What would the syllabus be for a TeMBA?

{Edit 2} Here's the link:

https://news.ycombinator.com/item?id=11894955

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:05PM (#11894968)
This needs to be solved demand-side, not supply-side. If you graduated a class of TechMBAs right now they wouldn't have any jobs to use their new skills.

Flip it around: if Google opened up a new role for "Active engineers with MBAs", and presumably a few others followed suit, a top school or two (GSB/HBS/CBS/etc) would create the curriculum & recruiting plan to fill it. (Most likely Google could do this together with a school, they tend to have very close relationships.)

Re:Ask HN: I don't enjoy being a CTO. Now what? by nostrademons on Monday June 13, 2016 @11:23PM (#11899528)
This is basically the APM program in Google. Google stopped hiring PMs without a technical background (either CS coursework, or professional experience as an engineer) in 2008, because they found that the PMs they did hire with no technical experience universally sucked.

They also have (had? it's been 2 years since I was there) an active rotation program between eng and PM roles, with the opportunity to transition permanently. A number of my friends did it; I'd seriously considered it, but my manager was willing to let me do PM-type roles without formally switching job titles.

Re:Ask HN: I don't enjoy being a CTO. Now what? by nekopa on Monday June 13, 2016 @12:28PM (#11895154)
Is this not a classic chicken-egg scenario?

I think if you graduated a class of TeMBAs right now, they would have jobs just because of the MBA side of the equation.

And, I think they would kick-ass in what ever job they take because of their tech skills. Even stooping as low as to say that their Excel skills would rock because they know how to masterfully program macros.

But WOW, yes, if someone like Google got behind a program like this, it would take off like nobodies business.

But I think we really need to get regular businesses (Davids, not Goliaths) behind this. And somehow, show them the benefits of a well rounded TeMBA graduate.

Re:Ask HN: I don't enjoy being a CTO. Now what? by roymurdock on Monday June 13, 2016 @01:13PM (#11895488)
An MBA doesn't really confer any skills that couldn't be acquired from 6 months of actually working/managing at your target company - it's seen as more of a networking tool, and a way for someone to hit the reset button and shift into a different field, or to get a raise within a traditional consulting/corporate migration path.

So I have to agree with DelaneyM that the crux of the issue is demand-side: where is the need for specific managerial jobs that require a baseline technical understanding (to estimate timelines, speak intelligently about the product with clients, etc.) as well as basic business skills (negotiation, project management, strong network for potential clients) that is worth the salary that an individual who just invested $200k and 2 years worth of time will be asking?

Re:Ask HN: I don't enjoy being a CTO. Now what? by tormeh on Monday June 13, 2016 @01:56PM (#11895779)
This already exists: http://www.ntnu.edu/studies/mtiot . It probably exists in the US too.

The demand for them is crazy-high. Leadership roles in Norway are very rarely filled by hiring fresh graduates, but the consultancies lap them up.

It's an integrated 5-year master. They do engineering stuff the first three years, specializing in the third, and then they do two years of economics/business/leadership. It's very specialized, and to me it looks like they are OK at their chosen engineering discipline and OK at their chosen business discipline but not very well rounded. That's the sacrifices you have to make when you make a business/engineering combination but try to avoid making master-of-nones, I guess.

Their choices are (in each stage they can only chose one. 3. year available choices depends on 1/2. year choices):

1/2. year: CompSci/high-voltage/machine/marine

3. year: AI/digital economics/software/el. energy/heat & energy processes/production/marine projects and logistics/marine technical operations

4/5. year: economic optimization/project leadership/purchasing and supply/reorganization/investment and finance/innovation and entrepreneurship/HSE/strategy and business development

Re:Ask HN: I don't enjoy being a CTO. Now what? by hkhall on Monday June 13, 2016 @10:47PM (#11899428)
There is something similar in the US at Dartmouth (yes it has a slightly goofy name): http://engineering.dartmouth.edu/academics/graduate/innovati...

Basically they let you cross register with some Tuck Classes while doing research that is more self-directed than normal.

Source: I am in the program

Re:Ask HN: I don't enjoy being a CTO. Now what? by __derek__ on Monday June 13, 2016 @01:53PM (#11895760)
Cornell has launched a program[1] that aims to be what you're describing here. There's also a Technology Management MBA from the University of Washington's Foster School[2], although it's more of a technology-oriented part-time MBA than a traditional MBA targeted at engineers.

[1] Cornell Tech MBA: http://tech.cornell.edu/programs/masters-programs/johnson-co...

[2] UW Foster Technology Management MBA: http://foster.uw.edu/academics/degree-programs/technology-ma...

Re:Ask HN: I don't enjoy being a CTO. Now what? by dragonwriter on Monday June 13, 2016 @01:56PM (#11895777)
> So why don't we, as an industry, talk to the Universities, and say that we really need a new program, let's say a TechMBA?

Its already been done, and there are a wide-number of tech-specialized MBA programs.

Re:Ask HN: I don't enjoy being a CTO. Now what? by qihqi on Monday June 13, 2016 @02:03PM (#11895827)
Lots of university have MBA-MEng joint program that will award 2 degrees upon completion. MIT's LGO program is such a program.
Re:Ask HN: I don't enjoy being a CTO. Now what? by giaour on Monday June 13, 2016 @01:02PM (#11895411)
You might be right about the startup world, but there is a massive demand for techie MBA/business-y Eng at the sub-VP level in big tech companies with tiered management. That sounds like exactly the skill set you would need to manage a division or org of one of the big 5.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @01:14PM (#11895493)
Demand & applicability != opportunity.

Maybe it's chicken & egg, maybe it's a Unix philosophy applied to organizational design (https://en.wikipedia.org/wiki/Unix_philosophy#Do_One_Thing_a...), but there is virtually no true demand for an engineering MBA.

I'm happy to be proven wrong with a counter-example of a posted job description. Try to find one example of a hybrid position with more potential and better pay than a corresponding pure engineering role.

Re:Ask HN: I don't enjoy being a CTO. Now what? by sailfast on Monday June 13, 2016 @10:45AM (#11894258)
Thanks - this is really interesting and thought provoking feedback.
Re:Ask HN: I don't enjoy being a CTO. Now what? by rorykoehler on Monday June 13, 2016 @12:50PM (#11895335)
I always viewed tech as a tool to improve the other aspects of the organisation. What are you doing with tech if you are not improving either operations, marketing or finance?
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:58PM (#11895385)
It could also be your product.
Re:Ask HN: I don't enjoy being a CTO. Now what? by OpenDrapery on Monday June 13, 2016 @02:44PM (#11896241)
I think the difference between line of business software and companies that are actual software companies is so huge that it starts to make no sense to compare them.

I've worked on technology that goes out the door and contributes to the company's revenue stream, and I'd have been insulted if someone said I was in "IT". The cultural differences between that and truly working in the IT cost center is massive.

Most people who spend the careers working for banks and insurance companies never see the other side of the chasm.

Re:Ask HN: I don't enjoy being a CTO. Now what? by rorykoehler on Tuesday June 14, 2016 @12:51AM (#11899863)
In which case it's just one step removed. All products I have ever come across fix a pain point in one or more of the areas mentioned.
Re:Ask HN: I don't enjoy being a CTO. Now what? by jwatte on Monday June 13, 2016 @02:22PM (#11896014)
My take is that, at certain scale, the biggest problem is getting all the people to pull in the same direction. Technical leadership can define /how/ to pull, which can have a 10x multiplier if correctly implemented in the organization, but that implementation is a number of battles with messy human wills, which require psychology, not technology. As a CTO you may be able to hire directors who are good people pushers, to delegate most of that, or even perhaps a VP Eng if your company is big enough.
Re:Ask HN: I don't enjoy being a CTO. Now what? by shdon on Monday June 13, 2016 @12:13PM (#11895020)
DelaneyM, your posts here, especially when combined, would make a pretty compelling article in their own right. Please consider writing them into a blog post and submit that to HN as well.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @03:40PM (#11896784)
Thanks!

But the world (particularly our corner of it) is full of smarter people saying more interesting things. I feel like the best way I can contribute is not distracting readers from doing.

Re:Ask HN: I don't enjoy being a CTO. Now what? by shdon on Monday June 13, 2016 @04:10PM (#11897136)
I think you underestimate yourself. Or overestimate other people :) There are plenty of uninteresting or non-useful comments posted everywhere, including on HN. Yours in this thread are both interesting and useful.
Re:Ask HN: I don't enjoy being a CTO. Now what? by seangrogg on Monday June 13, 2016 @04:15PM (#11897197)
As a counterpoint, I use these distractions to center myself. There likely are smarter people saying more interesting things, but HN's feed also sometimes has things like "Java StringBuffer and StringBuilder performance". I would much rather read about a "TechMBA/TMBA/TemBA/STEMBA" proposal than about performance of utilities of strings in a language I don't use.
Re:Ask HN: I don't enjoy being a CTO. Now what? by skewart on Monday June 13, 2016 @02:44PM (#11896248)
I second this! I would love to read a blog post - or a series of them - where you explain your thoughts in more depth.
Re:Ask HN: I don't enjoy being a CTO. Now what? by goshx on Monday June 13, 2016 @10:49AM (#11894284)
It's funny how you hit the MBA nerve there. I've been considering going that route, but with the intention to get more involved with people from different backgrounds than anything else. I don't want the MBA to move away from my position as CTO, but to improve my abilities in other areas of the business and networking purposes. Would you still recommend not getting the MBA in that case?

This is all in preparation to take the entrepreneur route, while I can't simply take it right now.

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @10:57AM (#11894354)
An MBA provides only one thing: the opportunity to stop doing engineering.

Do you want to stop coding/building things, and instead build teams & business? Then do an MBA. There really is a lot to learn; it's not the irrelevant piece of paper it's often made out to be. The usual caveats apply (right school/program, work hard, etc.)

Do you want to be a higher-impact engineer? Don't do it. Apply to YCombinator, build more part-time projects, start a "sell stupid shit" on eBay company and learn the ins & outs of incorporation/taxes/financial tracking/etc.

Getting better at business & networking is a great idea, but an MBA for that alone is overkill.

Re:Ask HN: I don't enjoy being a CTO. Now what? by mxuribe on Monday June 13, 2016 @11:19AM (#11894553)
> An MBA provides only one thing: the opportunity to stop doing engineering.

Holy smokes! If your statement is true, then here's me running in the opposite direction of that mba.

+1!

Re:Ask HN: I don't enjoy being a CTO. Now what? by eitally on Monday June 13, 2016 @12:19PM (#11895069)
Think about it: MBAs learn non-engineering skills, so how could it possibly be otherwise. If you get an MBA and continue engineering work, then by definition you're not leveraging your MBA, and vice-versa. That's a huge simplification, of course and I don't completely agree with the OP, but that's the gist of her point.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:27PM (#11895135)
There are exceptions to every rule, but I'd say within the context of "jobs at existing large employers of MBAs and/or Engineers" the true intersection of engineer & business is nonexistent.

(There are lots of places where it'd be advantageous to have both skills, but never necessary, which is my underlying thesis.)

Re:Ask HN: I don't enjoy being a CTO. Now what? by ddebernardy on Monday June 13, 2016 @11:45AM (#11894787)
It also provides access to an alumni network.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:08PM (#11894989)
Not nearly as relevant/helpful it's often made out to be.

Executives are more helpful than most give them credit for. If you're a credible contact with real experience, and authentically ask someone for input or advice, most are happy to chat.

The thing about the vaunted "HBS network" is that if you're qualified to get in to HBS, you're extremely likely to be otherwise credible; those who wish they had access to the alumni network also tend to not have enough meat on their CV to get access either way.

I personally suspect that the most important networking aspect of an HBS degree is just humanizing executives and learning how to communicate with them. If you've got those two things down, actually connecting is much easier.

Re:Ask HN: I don't enjoy being a CTO. Now what? by ddebernardy on Monday June 13, 2016 @12:21PM (#11895079)
Interesting how you put it. The "devaluation of higher education" bit of this column struck a chord in me back then. It sort of lays out a similar point in a slightly different way:

http://web.mit.edu/krugman/www/BACKWRD2.html

Time will tell. :-)

Re:Ask HN: I don't enjoy being a CTO. Now what? by vthallam on Monday June 13, 2016 @12:23PM (#11895097)
> most important networking aspect of an HBS degree is just humanizing executives and learning how to communicate with them

So true! Probably this is the most important thing a good business degree provides.

Re:Ask HN: I don't enjoy being a CTO. Now what? by unhappycto on Monday June 13, 2016 @10:27AM (#11894134)
Thanks for the reply. I had thought of doing an MBA a couple of years ago, albeit fleetingly. I don't think that will solve things in this current situation though :)

I also agree that perhaps my issue is more of building things rather than strategic input. After all, when building things for my own business is when I'm most happy so it's good to hear a similar conclusion.

Good luck with your new venture!

Re:Ask HN: I don't enjoy being a CTO. Now what? by jeffcwang on Monday June 13, 2016 @03:56PM (#11896962)
I'm also an HBS grad with a technical background (BS/MS comp sci + 7 years of coding before b-school). While I agree with most of your sentiments, I feel compelled to offer a slightly different view.

Regarding your comments around the CTO position, I think that is because HBS didn't pay attention to tech/startups until about 5 years ago (i.e.: Field 3, Startup i-lab, tighter recruiting with silicon valley). I'm guessing that in 10 years, we'll see more as the current batch of students mature in their careers and have the CTO position available to them. Additionally, most of the technical students in my class (myself included) decided to pursue the PM track for the very reason you highlighted -- to have a seat at the table when making significant business decisions. In my current role, I run product, engineering, and operations. I still code (python/flask/node/postgres) but I'm also responsible for the product roadmap and operations (supply chain, recruiting, call center efficiency). I have a direct impact on revenue/managing costs and driving results through the metrics we measure. More importantly, I work directly with the CEO and have even had the opportunity to present to the Board. I feel this wouldn't have been possible with an MBA.

tl;dr: An MBA can actually be helpful for technical folks. In looking holistically around product/operations/sales, the actual code is probably one of the less important things in achieving business goals. Take a PM track if you want to have broader impact outside of just dev work (but with the option value to continue coding if you like).

Re:Ask HN: I don't enjoy being a CTO. Now what? by paulsutter on Monday June 13, 2016 @01:42PM (#11895684)
> Unfortunately, there's no real place in the world for a highly technical business leader.

So how do you account for Mark Zuckerberg, Elon Musk, Larry Page, and so on?

I think you meant to say "there's no place at Dronecorp for a highly technical business leader". It's logical that Dronecorp should hire Harvard MBAs who score high on agreeableness and are skilled at showing each other powerpoints.

Re:Ask HN: I don't enjoy being a CTO. Now what? by tracker1 on Monday June 13, 2016 @01:45PM (#11895708)
See the last statement in the comment, "The only truly successful technical leader is the founder..."
Re:Ask HN: I don't enjoy being a CTO. Now what? by paulsutter on Monday June 13, 2016 @01:52PM (#11895751)
Google and other well run companies have skilled technical people at all management levels.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @03:09PM (#11896453)
I'd love to meet one, or see a job description for such a role.
Re:Ask HN: I don't enjoy being a CTO. Now what? by nostrademons on Monday June 13, 2016 @11:29PM (#11899548)
When I was at Google my entire management chain had the title "software engineer" (except Alan Eustace, who officially had the title "VP of engineering" but had a hardware engineering background, and Larry Page, who had the official title of "CEO"). That was 6 levels up, including me. Amit Singhal (who was 3 levels above me and responsible for a department of 2000 people or so) was still titled "software engineer".
Re:Ask HN: I don't enjoy being a CTO. Now what? by dmitrygr on Monday June 13, 2016 @05:39PM (#11897925)
>So how do you account for Mark Zuckerberg, Elon Musk, Larry Page, and so on?

Is this a game of "which of those three does not belong"?

If so, too easy...

Re:Ask HN: I don't enjoy being a CTO. Now what? by aws_ls on Monday June 13, 2016 @12:53PM (#11895356)
>Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Good move. All the best. I totally agree with this statement. For a technical person to become the founder gives the most amount of freedom. I have personally experienced this in my career. Working for corporates, I was often the tech lead of a project, with somebody else to manage the team, and particularly in Indian culture manager role assumes a relatively powerful role, and the tech person, is often frustrated. Even though you may feel, that it will be better off playing both roles, by oneself.

On this last point, I feel several tech people, although very able, often lack the confidence to play managerial roles. Have seen a friend who is CTO and very good, playing subordinate to his co-founder who is CEO. I feel he can play both roles, by himself and do it better. But can't help it, if he himself doesn't feel that way.

So, if you are feeling frustrated as a CTO, and want to have freedom while being able to get your hands dirty (programming, I mean). Being a founder, or even an equal co-founder should serve you well. If you can make it sustainable, nothing like it.

If you can make it sustainable, there is this risk of complacency. You may be too satisfied with just a lifestyle business. But that's another struggle & another story!

Re:Ask HN: I don't enjoy being a CTO. Now what? by knodi123 on Monday June 13, 2016 @10:16AM (#11894048)
> Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Best of luck!

Re:Ask HN: I don't enjoy being a CTO. Now what? by JohnnyConatus on Monday June 13, 2016 @02:09PM (#11895874)
I'm an experienced CTO without an MBA but I largely agree. Having an MBA and continuing as a CTO employee doesn't make a lot of sense. I have a decent amount of business knowledge thanks to working at an accelerator, being an early employee at a successful start-up, and consulting.

However, most organizations want one thing from their CTO: deliver tech that fulfills the promise of what we sold. Sure, you'll have some product input, but in most cases you will be excluded from overall business strategy other than to answer "when can we have it?", or if you're lucky, "what are our options?"

This is true for a number of reasons, including:

- Maybe the CTO shouldn't be making strategic business decisions. If it's not a consumer start-up, the CTO is often not the most clued into the market, either for lack of access or because they're so busy managing the delivery of the solution.

- Stepping on toes. In a perfect world, no one would get threatened if you see something on someone else's turf and point it out as gently as possible. We don't live in that world.

Personally, I will most likely found my own company, knowing fell well that I will be the CEO and that my development tools will change to communication and money management. An MBA could be helpful for this but it's not essential, from what I've seen.

Re:Ask HN: I don't enjoy being a CTO. Now what? by LCDninja on Monday June 13, 2016 @01:46PM (#11895717)
> Unfortunately, there's no real place in the world for a highly technical business leader.

I'm not sure I understand what you're saying here. As I understand it, the history of Silicon Valley was written by highly technical business leaders. They might not be writing code, but they're sure providing technical guidance - sometimes on a highly granular level...(e.g. famously Bill Gates micromanaging date/time storage in new language development when MS was a billion dollar company).

I contest that if you're highly technical, it's very difficult to step away from that knowledge (especially when you're seeing things going wrong). Not a bad thing?

Also - congratulations on becoming a founder! Best of success to you!

Re:Ask HN: I don't enjoy being a CTO. Now what? by rms_returns on Monday June 13, 2016 @12:09PM (#11894996)
> You have to leave code behind at a certain point and spend your time on people/financial/planning issues

As an exceptional case, you can get into a large tech company like Google/Microsoft and thus enjoy a higher position while still being able to do what you enjoy (coding and technical stuff).

I was faced with this same dilemma when I quit my day job in a large multinational company and started freelance programming. As you said, there are career roadblocks in most companies when you are more technically inclined than managerial. Besides, there is no large employer like Google/Microsoft/etc. in my country, so freelancing is my only option.

Re:Ask HN: I don't enjoy being a CTO. Now what? by msgerbush on Monday June 13, 2016 @12:42PM (#11895269)
This is obviously a personal question, but as someone looking to transition from an engineer to more of a technical business leader, what would you consider the most direct and fulfilling path? It sounds like the ultimate goal is becoming a CEO/entrepreneur, but do you think the"increasingly unfulfilling" years as a CTO are necessary/unavoidable? How do you continue to get the sensation of building things, as you become further removed from the actual execution?

Thanks for your comments here, as an engineer considering an MBA and general career trajectory, this has been really helpful.

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:57PM (#11895375)
It depends on whether you want to end up in macro or micro business.

If ultimately you want to be an entrepreneur, then try to sign on as an early/founding engineer with a qualified and capable business team. You'll learn most of what you need to do it yourself by proximity. Alternatively, consider one of the better incubators/accelerators as a way to draw a living salary while executing over time with support from your peers in the program and mentors.

If you want to be CEO of Cisco, suck it up and be a non-building technical leader. Eventually you'll be able to absorb or grow your scope into a profit-centre of the business (engineering is usually a cost centre), and if you excel at that you can climb the rest of the way. This is really the only end goal for which it makes sense to do an MBA.

Re:Ask HN: I don't enjoy being a CTO. Now what? by msgerbush on Monday June 13, 2016 @01:33PM (#11895615)
Great, that's exactly what I suspected, but nice to hear from someone who's been through it already. Thanks, again, and good luck with your new venture.
Re:Ask HN: I don't enjoy being a CTO. Now what? by atmosx on Monday June 13, 2016 @02:01PM (#11895813)
> Unfortunately, there's no real place in the world for a highly technical business leader.

You were at MS. How do you call Bill Gates if not highly technical ? :-)

That said, I understand what you mean.

> Also, I'd really misdiagnosed my malaise. What I'd been missing was not strategic input, but the opportunity to build things.

Isn't that exactly what Steve Jobs was doing for a living at Apple (or Pixar)?

Again I understand what you're saying, but maybe not all companies/positions are so well defined as you make it sound.

Re:Ask HN: I don't enjoy being a CTO. Now what? by spinlock on Monday June 13, 2016 @02:58PM (#11896352)
Bill Gates was a drop-out, not an MBA. Steve Jobs was a ... wait for it ... drop-out but also not technical. Steve Wozniack was the technical founder of Apple.

If you really want to understand Jobs' talent, think about what Apple did when he left and how they changed when he came back. The technology didn't change that much (sure, Unix, but that wasn't _that_ big of a deal). The key difference is how they sold computers. After Jobs' was forced out, Apple started to copy the MicroSoft strategy: make computers highly customizable. Needless to say, that didn't work for Apple. After Jobs' came back, Apple stopped that strategy and started selling 3 options: good, better, and best. IMO, that's the real key of Jobs' Apple turn-around. He made it easy for people to buy computers.

Anyway, from that perspective, Jobs was all sales/marketing and not even close to what you'd consider a CTO.

Re:Ask HN: I don't enjoy being a CTO. Now what? by WhitneyLand on Monday June 13, 2016 @10:05AM (#11893950)
Given your technical background, be sure to involve someone with a strong sales/marketing point of view whether that's a cofounder, investor, or friend. Moreover make sure it's a relevant point of view. For example, someone with a great b2b pedigree won't necessarily add the most value if you're starting a consumer focused company. Most importantly, best of luck to you -
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @10:15AM (#11894029)
tl;dr: My first hire, and ideal cofounder, would be a really great CFO.

(When I frame myself as a technical leader, there's a quick assumption that I don't grok sales/marketing. If I introduce myself as a "Harvard MBA & angel investor", there's an immediate conclusion that code is beyond me... Nice to know that, when both are presented, the engineer wins. :) )

That said, sales is one of the easiest areas to hire for. I respect sales very much, most of my co-founders in the past have come from sales and I've learned a lot from them. But enterprise salespeople pay for themselves, have less/no expectation of equity, and expect to bounce from job to job every year. At some point I'll need a sales leader to manage a sales team (subdivide industries/regions, hire/fire, etc.) But that's not a founder-level role.

The biggest thing I need is going to be a great CFO. I'm getting into the logistics business (software eats fulfillment?), which is pretty capital-intensive. Debt is a better instrument for this than equity, but I have neither the time nor the temperament to secure that.

I'm broadly anti-VC, but may end up pitching primarily for the credibility with lenders & institutional investors.

Re:Ask HN: I don't enjoy being a CTO. Now what? by ddebernardy on Monday June 13, 2016 @11:50AM (#11894819)
Tip: you should leave your contact details on your profile, in case one is reading this.
Re:Ask HN: I don't enjoy being a CTO. Now what? by pcl on Monday June 13, 2016 @11:28AM (#11894635)
OT, but I greatly appreciate that you put your post summary at the top instead of at the bottom. I don't need a tldr summary at the end...

Was that a result of learning about executive summaries in your MBA program, or just something you picked up along the way?

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @11:42AM (#11894745)
Actually something I picked up in my summer at McKinsey.

For web content, we think of "above/below the fold". For executives/investors, the analogue is "above/below the [first screen of my blackberry | iPhone alert]".

Re:Ask HN: I don't enjoy being a CTO. Now what? by dpritchett on Monday June 13, 2016 @03:27PM (#11896653)
I like this phrasing from Wikipedia:

"The inverted pyramid is a metaphor used by journalists and other writers to illustrate how information should be prioritized and structured in a text (e.g., a news report). It is a common method for writing news stories (and has adaptability to other kinds of texts, e.g., blogs and editorial columns)."

Re:Ask HN: I don't enjoy being a CTO. Now what? by manigandham on Sunday June 19, 2016 @01:26AM (#11931892)
Looking at your linkedin background, I see you have some adtech experience. This is perhaps one of the few industries that could actually use this technical manager in the middle of the organization.

I'm building a martech company right now and this is exactly type of people I hope to gain, someone who knows how the tech really works while also understanding the needs of the business and our clients to make the right decisions. They don't need to code everyday but having a grasp of how ad serving works, how logging and reporting is done, how attribution occurs through cookies and other identification, etc. would all help to make them more informed and capable at producing value for our clients rather than turning products into undifferentiated mush that add no value, like the rest of the industry.

Or maybe I'm just that technical founder who will always have to mix the two disciplines and make the call myself - just wish there was a way to delegate this.

Re:Ask HN: I don't enjoy being a CTO. Now what? by aerovistae on Monday June 13, 2016 @10:21AM (#11894099)
> Unfortunately, there's no real place in the world for a highly technical business leader.

Cough Elon Musk

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @10:24AM (#11894116)
Cough solo founder.

> The only truly successful technical leader is the founder,

Re:Ask HN: I don't enjoy being a CTO. Now what? by aianus on Monday June 13, 2016 @11:29AM (#11894644)
Elon Musk wasn't even a founder at Tesla, let alone 'solo founder'. He joined as financier/chairman after R&D had begun and then took over as CEO some time after that.
Re:Ask HN: I don't enjoy being a CTO. Now what? by dasil003 on Monday June 13, 2016 @11:58AM (#11894906)
Good point, but it's not meaningful to the GP's original point. Self-made billionaire financiers write their own ticket, whether they are technical or not is merely a footnote.
Re:Ask HN: I don't enjoy being a CTO. Now what? by mxuribe on Monday June 13, 2016 @11:24AM (#11894604)
+1!
Re:Ask HN: I don't enjoy being a CTO. Now what? by nibs on Monday June 13, 2016 @02:05PM (#11895851)
A study of gifted people (probably relevant to a lot of people here) found that people who run, manage and/or start companies are the most satisfied with their careers: https://www.diva-portal.org/smash/get/diva2:281434/FULLTEXT0... and that gifted people in most other fields (law, medicine, etc.) as professionals are mostly good at what they do but indifferent about it. Start a company is great advise.
Re:Ask HN: I don't enjoy being a CTO. Now what? by tixocloud on Monday June 13, 2016 @01:49PM (#11895733)
Congrats on taking that leap of faith.

Essentially in the same boat as you and agree on the value of the MBA is in communications.

While arguably technical business leaders can significantly help organizations, businesses just don't see that way.

I've made the shift to the business side and don't do any coding at all. More time is being spent planning, analysis, presentations and building relationships.

I'm also set to start a new venture on my own as solo founder. Good luck!

Re:Ask HN: I don't enjoy being a CTO. Now what? by contingencies on Monday June 13, 2016 @10:16AM (#11894047)
Just wanted to say thanks for the anecdote and good luck.
Re:Ask HN: I don't enjoy being a CTO. Now what? by gspetr on Tuesday June 14, 2016 @02:52AM (#11900242)
> Unfortunately, there's no real place in the world for a highly technical business leader.

There certainly is, but I'll concede there might not be in a random startup.

For a counterexample, John Carmack seems to have done well for himself as Oculus CTO, even coding interesting things by himself:

https://news.ycombinator.com/item?id=10273235

Re:Ask HN: I don't enjoy being a CTO. Now what? by n00b101 on Monday June 13, 2016 @05:33PM (#11897876)
> Now I'm off to start a new venture as a solo entrepreneur. The only truly successful technical leader is the founder, and that feels right. My last day at my day job is June 30th. :)

Hey I'm off to start a new venture as a solo entrepreneur as well, my last day is June 30th, and I think we live in the same city. Neat!

Re:Ask HN: I don't enjoy being a CTO. Now what? by tim333 on Monday June 13, 2016 @01:40PM (#11895675)
>there's no real place in the world for a highly technical business leader.

Bill, Larry and Sergei, Musk and Bezos did ok

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @01:46PM (#11895714)
All of those people are founders.

My thesis is that there's no place in the world to be hired as an engineer w/ an MBA (which is comparably compensated to and inaccessible to "just" engineers or "just" MBAs), and no place within traditional hierarchies.

Re:Ask HN: I don't enjoy being a CTO. Now what? by tim333 on Monday June 13, 2016 @01:59PM (#11895795)
Ah - got you. Though I could counter with Satya Nadella who had a degree in Comp Sci and an MBA before joining Microsoft.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @03:07PM (#11896435)
But he hadn't been a practicing engineer, and never worked in an engineering or technical capacity at Microsoft.
Re:Ask HN: I don't enjoy being a CTO. Now what? by JOnAgain on Monday June 13, 2016 @01:42PM (#11895683)
Bezos is not highly technical. Very smart, and grasps concepts very quickly, but not highly technical by any stretch.
Re:Ask HN: I don't enjoy being a CTO. Now what? by tim333 on Monday June 13, 2016 @02:03PM (#11895825)
I wasn't sure about that one and googled him a bit. He actually seems more tech than you might imagine. Apparently bachelor's degree in EE/CS from Princeton, where he was Phi Beta Kappa, worked as a programmer, wrote part of the original Amazon code in C and there was this on Quora:

>At Blue he reads every technical memo released to the company. He also participates in weekly reviews, and the more data-rich the presentation the better. He'll stop and analyze every plot and gives feedback to the point you think he knows more about the subject matter than the actual presenter.

Re:Ask HN: I don't enjoy being a CTO. Now what? by bunnymancer on Monday June 13, 2016 @01:48PM (#11895725)
4 exceptional cases aren't much of proof of anything..

It's like saying racism and equality is resolved because Obama is president.

Re:Ask HN: I don't enjoy being a CTO. Now what? by tim333 on Monday June 13, 2016 @02:28PM (#11896068)
I'm not sure if it isn't the majority of leaders of major tech companies aren't technical. Rometty at IBM also did computer science, Zuckerberg was writing networking and ML software at school. Tim Cook might be an exception.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @03:18PM (#11896558)
Again, mostly founders.

Tim Cook though is my personal hero, and probably the truest counterexample. IMHO he's the most influential intersectional tech/business innovator of the past decade, and that includes Jobs. Only Hiroshi Mikitani comes close.

(Seriously, Tim: call me!)

Re:Ask HN: I don't enjoy being a CTO. Now what? by Kluny on Monday June 13, 2016 @01:48PM (#11895723)
Sure, but you're citing the most outlying of outliers as examples.
Re:Ask HN: I don't enjoy being a CTO. Now what? by personjerry on Monday June 13, 2016 @10:31AM (#11894155)
Any idea what your new venture will be?
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @10:39AM (#11894215)
Oh sure.

Software eats fulfillment, basically.

Currently FBA (http://services.amazon.com/fulfillment-by-amazon/benefits.ht...) is a 3B$ business without any competitors. There are good reasons for that: it's capital-intensive, technically/operationally/managerially challenging, and can only really be learned by doing.

I've just finished architecting & implementing a 30k package/day distribution system from scratch, I know I can do better. FBA is a surprisingly low bar to clear (they're mathematically/structurally constrained), and the industry hasn't really improved since the 90's. And with the right structuring it can be mostly funded through debt & advance receipts.

Basically, I'm going to pick up where FlexPort (https://www.flexport.com/) leaves off (literally! Ha, logistics joke!) Except in an even less sexy vertical. :)

Re:Ask HN: I don't enjoy being a CTO. Now what? by eitally on Monday June 13, 2016 @12:29PM (#11895166)
Depending which verticals you're trying to target, and who you think your end customers will be, there's a much larger shadow market for these kinds of services, currently being well served by a combination of "pure" logistics companies (UPS, FedEx, DHL, etc) and the largest contract manufacturers (Foxconn, Flextronics, Jabil, Sanmina, Pegatron, Quanta, Compal, and a couple more). If you haven't already researched this area, I think it would be a good way to spend a couple weeks.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:35PM (#11895211)
Integrated supply chains are incredibly complex once you get to that level, and not really candidates for a new entrant. The big logistics players you list go after those contracts rabidly, and newly signed contracts have payoffs measured in decades.

It's a massive industry, nearly 1.8T$ this year. (Yeah, that's a T.) I'll be happy with carving out my little 50B self-serve niche before digging into integrated supply chains. :)

Re:Ask HN: I don't enjoy being a CTO. Now what? by mxuribe on Monday June 13, 2016 @11:23AM (#11894596)
I would have thought UPS - and similar companies - would be considered competitors, which are no small fries! But, perhaps I'm looking at the wrong layer of the onion? And perhaps the layer you're referring to/hoping to operate in is n degrees removed from that. In any case, good luck!

+1!

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @11:48AM (#11894811)
tl;dr: different markets & different needs

It's not hard to get a dedicated fulfillment service once you've hit a decent size (say ~10k/day). But it's a very intensive sales process with long-term commitments.

They also tend to be both opaque and hard to integrate with other systems. Most use end of day EDI (yes, the 30yr old standard), some of the more "modern" ones have multiple drop times/day.

So major fulfillment providers (not UPS, which doesn't do fulfillment; but FedEx/Rakuten/etc.) are both inappropriate for fast-growing, flexible or seasonal loads, and don't support innovation in customer service for eCommerce companies.

FBA is a much more modern (and extremely successful!) service, but is only cost-effective if you're selling on Amazon. Their 3rd-party, non-branded service is not only prohibitively expensive but feature-light and under-developed.

Re:Ask HN: I don't enjoy being a CTO. Now what? by loopbit on Monday June 13, 2016 @12:15PM (#11895039)
As the ex-CTO of an ecommerce startup, I really hope you succeed and wish you the best of luck.

There's plenty of us, little guys that need logistics/fulfillment and the options just suck. There's a huge space between starting (when you can do it yourself with UPS/equivalent or even standard post) and when you hit a few thousand packages per day (when Fedex and similar is a decent option).

Re:Ask HN: I don't enjoy being a CTO. Now what? by totalrobe on Monday June 13, 2016 @02:43PM (#11896232)
What were your biggest challenges with standard post solutions?
Re:Ask HN: I don't enjoy being a CTO. Now what? by loopbit on Monday June 13, 2016 @05:24PM (#11897788)
The main one is that, at least with the providers I used (three, including Fedex) there was no api and no way to interface with their systems automatically, everything had to be done through archaic websites with a usability designed before the dot com boom or by phone. During busy times (christmas shopping, for example), we had several interns dedicated exclusively to handle sending the info (number of packages, destinations...) to the supplier and printing the shipping labels.

I think that when you reach the thousands of packages per day, you are offered those services, but as a small setup with 'only' hundreds of packages, the only option was to do it manually. We had a simple system to handle orders, inventory, manufacturing... It would have been a breeze to integrate an api with it to print the labels automatically to give the guys actually preparing the packages.

We didn't get a lot of issues that usually pop up when talking ecommerce (scammers, false orders), we didn't even get many returns (I only remember a couple of cases) but we did get a few packages that disappeared in transit with no explanation or, obviously, a refund. The process to report those was horrible, similar to cancelling a mobile phone contract and in most cases we had to simply write-off the package and send a new one to the customer (actually, we are waiting for the resolution of a case when a package worth a few thousand euros was lost, we might actually get back that money).

Another thing that was annoying, although I know it's understandable, is that to start getting discounts they require a volume that, as a new company or sole trader you are simply not going to get. Paying the normal rate for Fedex, for example, makes packages quite expensive when you are talking international (and the fact that I live in an island with a population of less than 10M people doesn't help). We basically kept shipping costs to a minimum by eating into our profit margin. We got less money, but helped improve the sales.

Re:Ask HN: I don't enjoy being a CTO. Now what? by danpalmer on Monday June 13, 2016 @11:48AM (#11894808)
This is an awesome idea and I wish you the absolute best of luck with it. As a software engineer in a startup that does our own logistics/fulfillment/warehousing/etc, I can say I'd love to see more modern products in this area.
Re:Ask HN: I don't enjoy being a CTO. Now what? by tamana on Monday June 13, 2016 @10:49AM (#11894278)
? The mid/senior leadership of the best known companies hires all thr available techie MBAs. There are few CTOs because a 50K employee company only has 1 CTO. Others are CEO, COO, CIO.

A mid/senior person at a big company is similar to a CxO at a small company.

Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @11:10AM (#11894465)
> The mid/senior leadership of the best known companies hires all thr available techie MBAs.

This is false, and also misses the point.

I went through two recruiting cycles at HBS (Harvard Business School), which is one of the largest (~1000/yr) and most representative business schools. I did not see a single position advertised which required actual engineering experience. I was also one of three people (in 1000) who had a job before school which required writing code.

There were plenty of companies which would have loved to hire a solid engineer, but the job they'd be hired into would neither require nor use those skills. I could certainly go work in Product Management at Google, for instance; but why would I want to? My better path to VP at Google would be as a coder (if I wanted to be a VP at Google).

> There are few CTOs because a 50K employee company only has 1 CTO. Others are CEO, COO, CIO.

There is 1 CTO in the HBS alumni database. There are more than 36,000 CEOs. CEO-CTO is probably ~2:1 in the real world.

ps: data mining the HBS Alumni database is fascinating, btw!

Re:Ask HN: I don't enjoy being a CTO. Now what? by vasilipupkin on Monday June 13, 2016 @11:52AM (#11894846)
Strongly doubting the assertion that it is easier to become a Google VP as a coder than a product manager. Product managers are responsible for the product and its P&L which is much more suited as training ground for VP than being a coder, in my opinion
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:02PM (#11894943)
A better 1:1 comparison is PM vs lead Engineer. They're at similar levels in the hierarchy.

There are idiosyncratic and systematic ways to consider this statement.

My personal belief is that it would be an easier path because I know myself to be very good at building products and supporting engineers, and relatively less interested in market research & networking.

In a more general sense, it's pretty easy to get a rough count of the number of product-oriented VPs at Google on LinkedIn, then count how many have PM backgrounds and how many came up through engineering (divided by the ratio of PMs to engineering managers). I did that analysis two years ago when I was considering Google, and it came up strongly on the side of engineer.

I'd be particularly interested to know if this has changed since, or if internal/better data suggests otherwise!

Re:Ask HN: I don't enjoy being a CTO. Now what? by eitally on Monday June 13, 2016 @12:26PM (#11895126)
I suggest that once you get to the senior manager level on both tracks they generally start to merge as both become less focused on technical minutiae and more focused on product planning and execution. Eng directors [outside of pure research areas] have to be as market/business savvy as PM directors, for sure.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @12:37PM (#11895229)
That's very likely true, but it doesn't say much about the relative access each has to a VP office.
Re:Ask HN: I don't enjoy being a CTO. Now what? by vasilipupkin on Monday June 13, 2016 @01:56PM (#11895776)
You are saying Google has a lot of VPs without MBA and no product leadership experience, without any prior experience of having P&L responsibility, strictly engineering experience? Perhaps, but I am skeptical. I'd like to see the data on that.
Re:Ask HN: I don't enjoy being a CTO. Now what? by DelaneyM on Monday June 13, 2016 @04:08PM (#11897110)
If you restrict it to product VPs, it was true as recently as 2014.

The set of Google VPs has a representative sample on LinkedIn. Prove me wrong.

Re:Ask HN: I don't enjoy being a CTO. Now what? by vasilipupkin on Monday June 13, 2016 @06:20PM (#11898214)
All the VPs who came through engineering that I found did so after having been early employees at one of the top tech companies. I buy that. But if you are going to climb the ladder now, I doubt you can do it through engineering at Google
Re:Ask HN: I don't enjoy being a CTO. Now what? by h1srf on Monday June 13, 2016 @02:28PM (#11896064)
I don't think HBS would be the best dataset to use though:

1. The CTO position probably didn't exist until the 90s so you'd need to restrict your dataset to something more recent

2. HBS doesn't generally attract tech people. All of the people that I know that went to HBS(~20) work in finance/consulting/non-profit. Some came from a tech background. Stanford may be a better choice. That was the vibe I got when I attended MBA info sessions at HBS and Stanford. Columbia had sort of a mix.

Re:Ask HN: I don't enjoy being a CTO. Now what? by mxuribe on Monday June 13, 2016 @11:20AM (#11894559)
+1!
Re:Ask HN: I don't enjoy being a CTO. Now what? by curiousDog on Monday June 13, 2016 @12:25PM (#11895110)
Your career is both fascinating and inspirational. Best of luck with your new venture.
Re:Ask HN: I don't enjoy being a CTO. Now what? by mxuribe on Monday June 13, 2016 @11:15AM (#11894522)
+1!