There's only one real answer. It's when you're ready to be a big company. But not just because you want to be a big company.
Heavy hitters (i.e. former executives of big companies) bring big company expectations. They expect to hire a big team. They expect that your product is ready to scale, and in B2B, ready to be packaged and sold down a channel. They expect that you know how to sell your product in a repeatable way, a way they can copy, optimize, and teach to new hires. They expect to move at a big company pace, and expect you have some semblance of big company processes.
These people, in general, do not know how to, and do not want to, live the kind of startup life you've been living -- the hours, the apparent chaos, the extreme frugality, the wearing of many hats. They won't love your product like you do. This will be a job for them.
Remember that they're almost always from big companies, but much less often did they help build those companies at the critical juncture -- the time before everything was working. The time before it was clear the company would succeed if it could just expand on what it was already doing.
These heavy hitters mostly expect that your company already works, fundamentally, and that you're hiring them to do more of it. If that doesn't sound like your company, you're not ready yet.
And if you hire these folks before you're ready, it will probably destroy the company. It's a one-way function. By their nature, they'll drive out your early hires and scale your costs. If your revenues don't scale comparably -- because you didn't actually have product/market fit -- then those heavy hitters and the teams they brought on will leave when they see the writing on the wall. Leaving you, alone, back at zero.
To become a senior executive at a large company you have no choice but to stop doing real work and devote your time 100% to internal politics, because you are competing for a limited number of promotions with people who will do that. The real work skills of a “heavy hitter” atrophied long ago... and all the politics of their former employer won’t help them in their new job unless they can import all their cronies too... basically there is NO reason to ever hire one of these types.
I have seen that happen with a $100 million s/w company. It was very depressing. Not only where the people they brought in thinking of themselves as “heavy hitters”. They where also poor at their jobs. They wouldn’t have done particularly well even if the company was ready to scale. That of course didn’t help. It was sad.
This is a really good summary of how it tends to play out in the real world.
In particular it is the readiness aspect. When time has come to actually think like a business, and be less of a passionate founder of your own little baby.
Lastly, on the last point, I'd offer a slightly different pov in that these people will drive out cost that you might have overlooked, or have some sort of personal opinion on. These people will be ruthless on empty costs and you need to be okay with that.
In your opinion, where are the guys who did help build other companies during critical junctures? Do all of them stay with the companies they've helped build? I'm sure they're senior level too, perhaps being described with the same keywords (and thus indistinguishable) from the "carry-on heavy-hitters" you described?
I think you need senior _technology_ people from day one, if you want to build to scale, and you don't really want to pay to build everything twice _and_ pay for extreme server costs _and_ pay to migrate from the old to the new system.
Maybe this means something different than "Heavy Hitters". I've never run a huge company division; I prefer to work in a startup environment, and except for a short stint at Amazon, that's where I've stayed. But I have been able to step into small companies as an interim CTO and turn their technology from a mess that won't scale and that was written by junior developers into something that will scale cleanly from day one.
And I typically do this by throwing away most of what was there to begin with and rebuilding from the ground up. Most junior devs just don't have good architecture and design in their blood like a strong senior developer. Which means there's 2-3x extra work to prevent the current system from dying or failing during the transition process ("Changing the tires while driving at 60MPH").
If instead you have someone like me drive the project from the start, when the project is _finally_ seeing traction you can focus on adding features your customers are demanding and pivoting if necessary. And you don't end up hemorrhaging money by paying for 50x as many servers as you would need if you'd start with a strong architecture.
And the funny thing? Hiring a strong dev early on will likely get you to a working product much sooner than several junior devs, and you overall save money due to launching sooner. So it's a huge win. And a lot of the time, founders _are_ junior devs (I've been coding for 30 years; anyone with less than five years is junior, from where I sit, and a decade is bare minimum to be "senior").
But everyone wants to cut costs and hire the $10/hour developers, or the green developers fresh out of college. And now articles like this are being written that imply that you shouldn't even hire a "heavy hitter" until some vague criteria have occurred...
Well, good luck with that. You might be able to pivot and improve your technology in time. Or you might end up going the way of Friendster, pissing off your user base because your site keeps failing, and by the time you have it working reliably, they've all left. [1] Or maybe the fact that they left allowed it to work reliably? Hard to say.
Spot on and I just escaped a company that hired a junior dev as their lead. It was horrendous. I don't want to call out the junior to management because he has kids but he's really screwing up their product and they don't even realize it because they know nothing about technology
Reading this article I feel like I just got done talking to a C-.
Grand words with strong advice, but at the end I'm not sure if the topic point "when C-level?" is any more clear in my head.
I apparently need to be:
- Tired, but not so tired I can't survive the C- interviews
- Willing to delegate, but know what stuff is OK to let go
- Honest
Yet these seem more like qualities I just need in hiring. I'm tired of, or not good at, doing X job. I'm OK with not personally doing X. I tell the truth and expect new hire doing X to give it back. If all 3: hire someone for job X.
The main version for C- still seems to be, "the VCs are becoming a huge thorn in my side" whether I admit they have a point or I just want them to calm down.
Perhaps I'm just far too cynical about C- value these days. "We're strongly pushing to accelerate our core strengths and metrics while increasing overall investor value."
We should get rid of this whole "C-" idea anyways.
Comes from rigid social ideas about how to organize companies, that tends to push down the importance of product and technology roles in favour of giving more social power to roles that in practice actually contribute way less.
Yeah plus following a few links to his other posts, the guy rants about arrogant jerks while constantly using arrogant jerkish language. It seems like a lot of his criticism might be projection.
Interesting essay. I really resonate with the honesty point, when the CEO especially has honesty issues the whole enterprise can go to hell in fairly short order.
I have also been in these conversations where really it's the investors who want someone "with experience with these things" and the founding staff is being cajoled along. A couple of times this worked out to an advisory role at the board level. It lets the founder get advice without feeling compelled to take it, and it lets the board feel like they have access to another point of view that might let them see things they are missing.
The key though is that the executive team has to internalize that they and not their engineers or sales or marketing people are holding back the company. That can be tough, especially if your CEO is short on self awareness.
'Bring in the heavy hitters' strikes me as an odd way to phrase 'the investors have decided to take your company away from you and put someone else in charge who may or may not understand the business'.
Surely the correct way to react to that is to start by asking what you've done wrong, and whether you can fix it? If the investors are just being assholes for the sake of it, you've got a fight on your hands, but hopefully that's not the typical case.
Unless it's a case where you don't want to run a big company? But the article didn't seem to be talking about that.
[+] [-] tc|8 years ago|reply
Heavy hitters (i.e. former executives of big companies) bring big company expectations. They expect to hire a big team. They expect that your product is ready to scale, and in B2B, ready to be packaged and sold down a channel. They expect that you know how to sell your product in a repeatable way, a way they can copy, optimize, and teach to new hires. They expect to move at a big company pace, and expect you have some semblance of big company processes.
These people, in general, do not know how to, and do not want to, live the kind of startup life you've been living -- the hours, the apparent chaos, the extreme frugality, the wearing of many hats. They won't love your product like you do. This will be a job for them.
Remember that they're almost always from big companies, but much less often did they help build those companies at the critical juncture -- the time before everything was working. The time before it was clear the company would succeed if it could just expand on what it was already doing.
These heavy hitters mostly expect that your company already works, fundamentally, and that you're hiring them to do more of it. If that doesn't sound like your company, you're not ready yet.
And if you hire these folks before you're ready, it will probably destroy the company. It's a one-way function. By their nature, they'll drive out your early hires and scale your costs. If your revenues don't scale comparably -- because you didn't actually have product/market fit -- then those heavy hitters and the teams they brought on will leave when they see the writing on the wall. Leaving you, alone, back at zero.
[+] [-] gaius|8 years ago|reply
[+] [-] bjelkeman-again|8 years ago|reply
[+] [-] sekasi|8 years ago|reply
In particular it is the readiness aspect. When time has come to actually think like a business, and be less of a passionate founder of your own little baby.
Lastly, on the last point, I'd offer a slightly different pov in that these people will drive out cost that you might have overlooked, or have some sort of personal opinion on. These people will be ruthless on empty costs and you need to be okay with that.
[+] [-] gota|8 years ago|reply
[+] [-] to3m|8 years ago|reply
[+] [-] SomeCallMeTim|8 years ago|reply
Maybe this means something different than "Heavy Hitters". I've never run a huge company division; I prefer to work in a startup environment, and except for a short stint at Amazon, that's where I've stayed. But I have been able to step into small companies as an interim CTO and turn their technology from a mess that won't scale and that was written by junior developers into something that will scale cleanly from day one.
And I typically do this by throwing away most of what was there to begin with and rebuilding from the ground up. Most junior devs just don't have good architecture and design in their blood like a strong senior developer. Which means there's 2-3x extra work to prevent the current system from dying or failing during the transition process ("Changing the tires while driving at 60MPH").
If instead you have someone like me drive the project from the start, when the project is _finally_ seeing traction you can focus on adding features your customers are demanding and pivoting if necessary. And you don't end up hemorrhaging money by paying for 50x as many servers as you would need if you'd start with a strong architecture.
And the funny thing? Hiring a strong dev early on will likely get you to a working product much sooner than several junior devs, and you overall save money due to launching sooner. So it's a huge win. And a lot of the time, founders _are_ junior devs (I've been coding for 30 years; anyone with less than five years is junior, from where I sit, and a decade is bare minimum to be "senior").
But everyone wants to cut costs and hire the $10/hour developers, or the green developers fresh out of college. And now articles like this are being written that imply that you shouldn't even hire a "heavy hitter" until some vague criteria have occurred...
Well, good luck with that. You might be able to pivot and improve your technology in time. Or you might end up going the way of Friendster, pissing off your user base because your site keeps failing, and by the time you have it working reliably, they've all left. [1] Or maybe the fact that they left allowed it to work reliably? Hard to say.
[1] https://en.wikipedia.org/wiki/Friendster
[+] [-] gonedevin|8 years ago|reply
[+] [-] SimbaOnSteroids|8 years ago|reply
[+] [-] araes|8 years ago|reply
Grand words with strong advice, but at the end I'm not sure if the topic point "when C-level?" is any more clear in my head.
I apparently need to be:
- Tired, but not so tired I can't survive the C- interviews
- Willing to delegate, but know what stuff is OK to let go
- Honest
Yet these seem more like qualities I just need in hiring. I'm tired of, or not good at, doing X job. I'm OK with not personally doing X. I tell the truth and expect new hire doing X to give it back. If all 3: hire someone for job X.
The main version for C- still seems to be, "the VCs are becoming a huge thorn in my side" whether I admit they have a point or I just want them to calm down.
Perhaps I'm just far too cynical about C- value these days. "We're strongly pushing to accelerate our core strengths and metrics while increasing overall investor value."
[+] [-] ExactoKnight|8 years ago|reply
[+] [-] BenoitEssiambre|8 years ago|reply
[+] [-] ChuckMcM|8 years ago|reply
I have also been in these conversations where really it's the investors who want someone "with experience with these things" and the founding staff is being cajoled along. A couple of times this worked out to an advisory role at the board level. It lets the founder get advice without feeling compelled to take it, and it lets the board feel like they have access to another point of view that might let them see things they are missing.
The key though is that the executive team has to internalize that they and not their engineers or sales or marketing people are holding back the company. That can be tough, especially if your CEO is short on self awareness.
[+] [-] oillio|8 years ago|reply
A lot of insightful gems on how to be better at leading in tech.
Also, their new book: https://www.amazon.com/dp/0995964300
[+] [-] ExactoKnight|8 years ago|reply
[+] [-] rwallace|8 years ago|reply
Surely the correct way to react to that is to start by asking what you've done wrong, and whether you can fix it? If the investors are just being assholes for the sake of it, you've got a fight on your hands, but hopefully that's not the typical case.
Unless it's a case where you don't want to run a big company? But the article didn't seem to be talking about that.