Ask HN: I don't enjoy being a CTO. Now what? • Hacker News Board

Re: Ask HN: I don't enjoy being a CTO. Now what?

#141

Post by eitally » Mon, Jun 13, 2016, 4:29 PM UTC

DelaneyM wrote: post #81

personjerry wrote: post #77

Earlier quoted context omitted.

Any idea what your new venture will be?

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,…

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?

#142

Post by nekopa » Mon, Jun 13, 2016, 4:34 PM UTC

nekopa wrote: post #62

If you are a hacker, then try to just hack the suckiness out of the job. Take a mental step back, and look at the business as a large computer, everyone's crap as bugs, fires as serious bugs and dealing with other managers as a high level architectural/resource allocation problem. Then get to hacking! Refactor the program (your role and tasks) until its running smoothly (i.e. you're happy) then start adding features.…

Hey, I aimed that ^ comment at OP, but someone else responded, and I just sent them the workbooks. So I just want to let you all know, the offer is open to anyone who contacts me.

The only thing I ask is don't mass share the files I send to you. Send to your friends or whatever, just don't put them up on megashare or some shit like that.

(I know that that will happen, but at least I tried :)

Re: Ask HN: I don't enjoy being a CTO. Now what?

#143

Post by DelaneyM » Mon, Jun 13, 2016, 4:35 PM UTC

eitally wrote: post #141

DelaneyM wrote: post #81

Earlier quoted context omitted.

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,…

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 th…

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?

#144

Post by DelaneyM » Mon, Jun 13, 2016, 4:37 PM UTC

eitally wrote: post #137

DelaneyM wrote: post #123

Earlier quoted context omitted.

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 ro…

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.

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?

#145

Post by borski » Mon, Jun 13, 2016, 4:40 PM UTC

gdb wrote a brilliant post about his experience that you should definitely read: https://blog.gregbrockman.com/figuring-out-the-cto-role-at-s...

Re: Ask HN: I don't enjoy being a CTO. Now what?

#146

Post by gumby » Mon, Jun 13, 2016, 4:41 PM UTC

The best translation I ever heard for "CTO" was "Chief Talking Officer" (from someone who had been "promoted" into the position.

Several different jobs can be assigned the title CTO but they are all technical leadership positions, not direct execution. The company should be getting leverage from your position -- you should be enabling the growth of the company, by being th external technical face of the company, by helping direct technical development internally, by representing the technical / architectural issues in the management team, or by defining the technical direction based on the exec team's decisions on company direction. Different companies need different mixes of these. BTW it's often a way to retire a founder without losing their technical input, or to keep them from meddling :-).

In your case you were hired on, so they wanted you to use your technical expertise to help guide the company (or keep the tech from getting into trouble -- but even on the execution side, that's the VP of Engineering's job).

So if it turns out this isn't what you really like doing, there's no harm in that: you should find something you would enjoy more, and help the company find someone else to do the job they need doing.

Re: Ask HN: I don't enjoy being a CTO. Now what?

#147

Post by msgerbush » Mon, Jun 13, 2016, 4:42 PM UTC

DelaneyM wrote: post #38

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…

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?

#148

Post by rorykoehler » Mon, Jun 13, 2016, 4:50 PM UTC

DelaneyM wrote: post #74

sailfast wrote: post #57

Earlier quoted context omitted.

> 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 /…

> 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. Owne…

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?

#149

Post by aws_ls » Mon, Jun 13, 2016, 4:53 PM UTC

DelaneyM wrote: post #38

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…

>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?

#150

Post by DelaneyM » Mon, Jun 13, 2016, 4:57 PM UTC

msgerbush wrote: post #147

DelaneyM wrote: post #38

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…

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 bec…

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.