What’s it like being a virtual CTO working with startups?

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Chief Technology Officer in Services (non-Government), 2 - 10 employees
I enjoy the flexibility it brings and the chance to support a non-tech founder with the tech side of things while they focus on what they do best. When the relationship works, the flexibility can be mutually beneficial. I started at my current organization as a virtual CTO, which is the way Kyco wanted it at the time. The thinking was that this would be the ideal way to go about it because Kyco is not primarily a technology business. But due to difficulties arising from a partnership with a managed services provider (MSP), I ended up having to come on full-time. It was taking up all my time and as a contractor, my bill would have been huge, so it was cheaper to bring me on as a part-timer first and then make it a full-time position.

When we were partnered with this particular MSP, they did things like setting up and managing our servers, looking after our emails, etc. But there were also layers and layers of project management that we didn't know about before because we thought everything was being done by this MSP’s internal resources, which wasn’t the case. As a result, we took over everything and all of that became my job. I'd never been an admin before but suddenly I was one. 

But the reason we went with that MSP at first was because their leader had a personal relationship with ours. And if I were to get hit by a bus, it would be difficult for anybody else in my organization to manage our technical resources, because none of them are technical. So using those managed services was also supposed to provide a bit of a protection because everything else is under my control.
Chair and Professor, Startup CTO in Education, 5,001 - 10,000 employees
I am in fact a virtual CTO. Since I joined this startup as the CTO, I have been working remotely for a year. It is boring since there is nobody to chat with during lunch, in the hallway, etc. It is not effective since I don't see what people are doing.
Vice President Global Head of Value Engineering in Software, 1,001 - 5,000 employees
Quite challenging to say the least. I was a Chief Growth Officer (not CTO) for a startup and given the frenetic pace, the constant huddles needed to ensure progress and active brainstorming needed around growth hacks and product features, this made it quite inefficient to get all this done remotely via conferencing tools. Instant brainstorms, idea gens, options analysis and testing are all a bit slower when done remotely and things to watch for. 
Sr. Vice President Engineering | Global Practice Head in Software, 201 - 500 employees
I had been in the role of CTO in my previous stint as both pre-COVID and during COVID (virtual) with a  startup.  Start-up has a different set of challenges than a well-established organization. Start-up's main focus is on the product/service and customer feedback they are building. They are not highly process oriented. In fact, the Engineers at the start need to be more passionate about the problem they are solving than any other process. During WFH as CTO (which I am relating to Virtual CTO), I observed both pros and cons. Pros: Team became flexible. Timing became flexible. Talent acquisition became easy (people were ready to join if we were allowing them as remote), usage of the best software and DevOps practices became mandatory, and a few others. Cons: Building a relationship with team became difficult, discussing/brainstorming solutions to problems became a little challenging, collaboration sometimes became a challenge (when one engineer's network not working), and the face-2-face connection where you get connected with your team emotionally also became difficult, etc.

So, in my opinion for a Startup, it might not be the best option to have a virtual CTO position because it is one of the key roles in the startup on which the entire organization's technology roadmap and solution of the problem for which the startup is opened are dependent. His/her in-personal interaction with the customer, key stakeholders, and the team is absolutely necessary for the success of the startup.

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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