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There's a huge difference between a Dropbox and an Uber here. Dropbox is a technology company. This is famously a place where deeply technical leaders can achi

There's a huge difference between a Dropbox and an Uber here. Dropbox is a technology company. This is famously a place where deeply technical leaders can achieve competitive advantage. The whole company exists to support the tech, so if the tech fails, bad. Uber (and most startups really) don't do tech, they use tech to drive sales. Of course the tech is important but it's a solution not a driver. Here I agree that a "well-rounded" tech-average CTO can be advantageous. Tech strategy is where everything converges. If products literally live or die by it, you better have a crack technologist at the top.

nickelcitymario 4y ago
For clarification: Are you suggesting Dropbox’s leaders aren’t well rounded? Or that they are and that they also need to be stellar engineers? I think you make a great point either way. I’d elaborate on that and say a business leader needs to deeply understand the product they make/sell, so if your core product is tech, I agree and see your point. But I still think they need to be really good at all facets of the business. They still need to understand the market and how to promote and how to close sales. Those skills don’t really develop if the only thing you do is engineering. Take HubSpot’s CTO Dharmesh for example. Brilliant engineer! But he applies his curiosity to understanding people and markets and solving unsolved problems. He understands the whole business. He also understands his own shortcomings and surrounds himself with people with complementary skills, because he knows full well that engineering alone isn’t enough.
- dshah 4y ago
  Thanks for the kind words. I don't consider myself a "brilliant" engineer. More of an experienced engineer. I've been building software products for 30+ years. I think the role of the CTO varies based on the scale of the company. This article on the types of CTOs is useful framing: https://www.allthingsdistributed.com/2007/07/the_different_cto_roles.html https://www.allthingsdistributed.com/2007/07/the_different_c...

nickelcitymario 4y ago

For clarification: Are you suggesting Dropbox’s leaders aren’t well rounded? Or that they are and that they also need to be stellar engineers? I think you make a great point either way. I’d elaborate on that and say a business leader needs to deeply understand the product they make/sell, so if your core product is tech, I agree and see your point. But I still think they need to be really good at all facets of the business. They still need to understand the market and how to promote and how to close sales. Those skills don’t really develop if the only thing you do is engineering. Take HubSpot’s CTO Dharmesh for example. Brilliant engineer! But he applies his curiosity to understanding people and markets and solving unsolved problems. He understands the whole business. He also understands his own shortcomings and surrounds himself with people with complementary skills, because he knows full well that engineering alone isn’t enough.

dshah 4y ago
Thanks for the kind words. I don't consider myself a "brilliant" engineer. More of an experienced engineer. I've been building software products for 30+ years. I think the role of the CTO varies based on the scale of the company. This article on the types of CTOs is useful framing: https://www.allthingsdistributed.com/2007/07/the_different_cto_roles.html https://www.allthingsdistributed.com/2007/07/the_different_c...