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My company is scaling and I need to focus on strategy as an IT leader. When should I hire a dedicated resource to handle the traditional IT tasks?

As you think about growing IT work, consider taking advantage of those outsourcing opportunities. I've built out from a very small team and I am always somewhat reluctant to hire. Outsourcing is a good option when you are a small but growing company. People are always saying, "You should hire a help desk person." But if you do that and then that person goes on vacation, you have nothing. You end up having very little ability to cope with the rise and fall of workloads. Help desk is a role that I tend to outsource until I have enough work for two or three full-time employees (FTE). At that point, there’s an opportunity to bring it in-house because I’m not depending on just one person. I have a couple of people and if someone quits, I'm not dead in the water for a while.

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Anonymous Author
As you think about growing IT work, consider taking advantage of those outsourcing opportunities. I've built out from a very small team and I am always somewhat reluctant to hire. Outsourcing is a good option when you are a small but growing company. People are always saying, "You should hire a help desk person." But if you do that and then that person goes on vacation, you have nothing. You end up having very little ability to cope with the rise and fall of workloads. Help desk is a role that I tend to outsource until I have enough work for two or three full-time employees (FTE). At that point, there’s an opportunity to bring it in-house because I’m not depending on just one person. I have a couple of people and if someone quits, I'm not dead in the water for a while.
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Anonymous Author
If you’re going home with a backlog at the end of the day and you are not happy with it, it's time to hire somebody. Whether you insource or outsource, it doesn't matter. Just get somebody to lend you a hand. I have worked extensively with management trainees and they are always happy to come and work. They’re ready for the slog and handle it better than most people you might hire as a full-time employee. They add great value because they have no baggage. In most cases, they also have no experience but they are willing to learn. In one of my organizations, we built an entire billing system with the help of six trainees and it cost me almost nothing compared to what I would have paid some of the larger global players. We even became a benchmark within the country for the way we did our billing.
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Anonymous Author
Time to value is the metric I would use because your time is more valuable if spent in other ways. Even if you hire an entry-level position, you could offload some of the more mundane tasks that you have to do day-to-day, because your focus is not just on the development side. You’re also thinking about market fit and how quickly you can go from ideation, to incubation, to scale. If you're somewhere between incubation and scaling, your time needs to be focused in that direction to be of most value to investors, customers and internal stakeholders. 
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Anonymous Author
Look at how you are spending your time: Which tasks are the most valuable for you? Are you spending an hour a week setting up a laptop, or are you spending half of every day on it? It comes down to where your time is best spent in terms of delivering value for the company. When you get to the point that you have to set up laptops all the time, then you can explore getting a company to do it for you. Ask yourself: What projects are you trying to achieve in order to grow the business and move forward? Which of those projects can you do on your own? What can you do with you, plus external partners? And then, what could you do better if you had an additional internal resource? I have had that conversation with CEOs before. I’ll say, "I can grow the IT team as fast or as slow as you'd like, but the question is: what level of capability do you want from the IT team? You have a list of projects as long as your arm, and I can do one of those per year if this is the current level of resource. I can do five of those per year if I have this level of resource. I can do 10 of those projects per year if we have this level of resource." Push it back to them as a business decision: How much capability do you want to have? And how does it help you grow the business?
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