What unexpected challenges have you faced as a startup CTO?

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Chief Technology Officer in Services (non-Government), 2 - 10 employees
There were many things I expected to handle as a CTO, but I didn't expect to be faced with a ransomware situation, especially one that wasn't done by some hacker. It was our own technology partners who turned off our cloud tenancies and it had nothing to do with us. It was just that two of our technology partners were fighting, and they’d decided to resolve their dispute by tanking a lot of businesses for two to three days. It was a mess. There was a lot of critical infrastructure and life-saving technology put at risk because these two tech companies decided to have a mudslinging match. We only have about 2 million people in Brisbane, so you can't burn bridges here.
CTO in Healthcare and Biotech, 2 - 10 employees
The one that comes to mind first is hiring top talent. As a startup, it's been a challenge to find and attract top software talent with high compensation competition from big players in the market. At some point, you realize you simply can't compete with the big dogs and start looking for people who are fantastic at what they do but are tired of the structure/roles at big companies. Finding those people and a compensation package that works for both of you can be difficult. 
Chief Technology Officer in Software, 11 - 50 employees
The two main challenges I have faced have been
- Hiring: Finding talent who are technically sound, but more importantly have the drive to push boundaries and solve problems creatively has been difficult. I think this also boils down to having the values/mission of the company clear to every employee and having them invested in the overall growth of the business.
- Training: Incetivising training and encouraging employees to keep up with the ever-changing technology landscape has proven to be a challenge as well. 
Chief Information Technology Officer in Finance (non-banking), 51 - 200 employees
I always believed that CTO would receive an unquestionable and eager reception to most technical advice and management of situations, just to take the role and realize that stakeholders from the business areas were particularly challenging and not as receptive of change, making the role a political matter over a technical one.
Chief Technology Officer in Transportation, 501 - 1,000 employees
- one of the most difficult challenge has been hiring a team which is as per your competency framework and within the budget.
- the other part is market being too easy and people dropping out at the last minute post offer. No matter what kind of interactions we would keep to engage with the candidate it did not matter. 
- The other has been remote work, where some people have to work too hard to cover up for people slacking. 
- Establishing processes that reduce redundancies and inefficiencies within the system.
-  Building culture of close collaboration as in remote work everything becomes mostly transactional and bonding at team level somehow misses out compared to working out of a place. 
- Learning through informal interaction has reduced a lot for younger folks and as a leader it becomes a challenge to help your team grow. 

Chief Technologist in Telecommunication, 10,001+ employees
Most of the time, the technical depth of a CTO is what a startup company needs to reply on. But as time goes by, the mindset of a CTO will need to grow with the business condition as the framework of the market keep on changing. Thus, a critical area for a startup CTO will be to continue the sharpening of his/her technical depth but in the mean time be open to changes! 

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