You can’t plan for your first 100 days as the CIO of a startup or small-cap (<500 users); 100 days is way too long to make an impact. Additionally there are countless articles on how to become an effective CIO in the first 100 days, but few of them truly apply to this space. Startups are a different beast entirely, and I would be shocked to hear that a CIO advised by a big four consultancy would even know where the floor was much less want to crawl around on it if they had to.
As the one now responsible for technology, your first 50 days are absolutely critical – you need to be delivering almost immediately, the trick comes with balancing the short term goals with providing real value to the company.
Immediately put out fires
Your career at the company, and the company itself, is not going to go anywhere if tomorrow there is a catastrophic data event or security breach. Take the first week or two to ensure the following are well under control;
- Intrusion detection
- Data compliance
The nuts and bolts of it is not important, backups can be to a USB drive you take home at the end of the day for all it matters – as long as they work. The first task is creating a secure baseline to make sure you aren’t going to immediately crash and burn, and take the company with it.
This is also the time to take technical stock of what is in the company stack. Where are things stored, what can you do better, where can you save some dollars immediately, who’s life can you make easier straight away. Being able to immediately take out pain points from your co-workers is an excellent gift to walk in with while you’re doing the next, and most important step…
Understand what the company does
If this is your first startup, prepare for a crash course in business. Aligning business and IT strategy happens a lot easier in startups than it does in larger businesses simply because of scale and the agility that comes with it. You need to know the business well, especially how it generates value for customers. The function of IT is knowing that process well enough that they can optimise it with technology.
You need to know who the company has as stakeholders, who is getting a service, who is getting a financial reward, who is generating value, and how is that value being delivered. This work starts before you even have the job, learn the company and what it does so you can go in with informed questions – few people are going to have an hour to sit down and get you up to speed, especially the people you’d really like to, so get them to fill in as few blanks as possible.
This will also give you some good visibility around the company, but more importantly it will give you the opportunity to help a lot of the business functions you are going to need to rely on for your success in the role later on. A big part of this will also be part of the next step;
Understand the rest of the senior leadership team
If you’re replacing someone, you’ve likely got relationships to mend – If you’re not, you’ve got relationships to build. Either way, you need to look at every other member of the SLT and understand them as you’d understand a customer. Where are their pain points, where is there unrealised value, how can you help them to better help their customers?
Most important for this is understanding YOUR part of the leadership team. What do you need to do in order for YOUR stakeholders to consider your work successful? Find out what is most important for you to achieve, and then weight that with the rest of your goals. This, too, is part of the pre-employment groundwork, as the job description itself is a call for help with a need to be met.
Discover your team
Startup tech teams are the weirdest of all weird animals. Due to the shorter history of the business, and the complete insignificance of titles, seniority is earned more than it is attached to a position. The same for you as the leader, you better know your tech well enough to actually contribute when you need to, or at the very least, you have to know exactly what you DON’T know. You’re looking for successors to your role, because your role will quickly grow out of control as the company grows – you need to pull the team along with you.
How you do this is completely up to the company, development heavy companies will work different to operations heavy ones. What you want is largely irrelevant in the early days.
Your environment is stable (enough), you understand what the company does, what the rest of the SLT is doing, and what team you have available – now comes some quick wins to immediately add value to the business, because so far it has been 4 weeks or so and you’ve achieved nothing of any real value.
First thing is first, organise your team. You should have a good understanding of who your strongest lieutenants are going to be. The logistics of how to organise depends greatly on the role and the business, but generally I try and get some quick wins together as fast as possible – there are always going to be projects either in flight, or easily completed with resourcing that will improve the standing of the department across the business.
Once you have these quick wins happening and the rest of the company stops holding their breath to see how you are going to land, it is time to focus on things that matter…
Create actual value for the customer (true value)
With the majority of BAU taken care of, you should be well versed in the company enough to make decisions and predictions on what is needed. You can interview top customers to see where else you can add value, you can meet with the rest of the department heads again to try to further add value (rather than just fact find).
You should be ticking over about 50 days, congratulations. Don’t stop now, the real work starts here!