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

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

#191

Post by simonebrunozzi »

I've been Tech Evangelist, Chief Technologist, and CTO in the past few years, both at large and small companies.

I think it's wrong to generalize - a CTO experience can be good or bad depending on several factors. It is entirely possible that you could be VERY happy in a similar situation, but with a different company.

Usually CTOs can be divided into engineering types, and outward-facing types. The former is hands on, codes, handles the engineering team, or at least has a strong bond/influence with the VP of Engineering. The latter is more in touch with customers, does more public speaking activities, and tries to condense feedback and requests in a way that the VP of Engineering can translate it into the product. Right now I'm the outward-facing type. I am enjoying it, mostly because the two co-founders are great individuals and leaders.

Let me know if you have questions - I would be happy to try to answer.

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

#192

Post by totalrobe »

loopbit wrote: post #130
DelaneyM wrote: post #116

Earlier quoted context omitted.

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…

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).

What were your biggest challenges with standard post solutions?

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

#193

Post by OpenDrapery »

DelaneyM wrote: post #152
rorykoehler wrote: post #148

Earlier quoted context omitted.

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?

It could also be your product.

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?

#194

Post by skewart »

shdon wrote: post #129
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…

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.

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?

#195

Post by robotpony »

You can also look at the CTO role as slightly different style of hacking; you program with teams, training, and planning in addition to setting technical direction and leadership. Many CTOs design and code as well (I do) as a senior-senior designer or architect, but you should think about the meta-programming as exciting on its own. Many senior level architects love to train and lead teams technically, and a CTO often focuses on these things. Senior level architects also curate the technology and design, which CTOs also often own. It's a great role, though it sounds like you may need to grow into parts of it. I suggest that it's totally worth it.

There are various ways to cast the role too; many organizations also have a VPE (or VPD) and other mid-level leaders. These roles can allow some flex in what a CTO is responsible for, though ultimately the role is responsible for direction in technology.

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

#196

Post by spinlock »

atmosx wrote: post #180
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…

> 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 u…

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?

#197

Post by DelaneyM »

tim333 wrote: post #178
DelaneyM wrote: post #167

Earlier quoted context omitted.

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.

Ah - got you. Though I could counter with Satya Nadella who had a degree in Comp Sci and an MBA before joining Microsoft.

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?

#198

Post by DelaneyM »

paulsutter wrote: post #173
tracker1 wrote: post #166

Earlier quoted context omitted.

See the last statement in the comment, "The only truly successful technical leader is the founder..."

Google and other well run companies have skilled technical people at all management levels.

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?

#199

Post by DelaneyM »

tim333 wrote: post #189
bunnymancer wrote: post #171

Earlier quoted context omitted.

4 exceptional cases aren't much of proof of anything.. It's like saying racism and equality is resolved because Obama is president.

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.

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?

#200

Post by dpritchett »

DelaneyM wrote: post #113
pcl wrote: post #107

Earlier quoted context omitted.

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?

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]".

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)."

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