We Are Oakleaf


Diptesh Mishra


What challenges does a CTO face when scaling an organisation?

All CTOs building and scaling any organisation face a number of challenges depending on various factors that vary with each organisation. In fact, there are so many challenges that the answer to this question can make an excellent multi-part blog post, article or even a whole book.

If I just focus on the specific aspect of hiring for the engineering team, finding high quality engineering talent has always been a challenge. The choice of technology stack is a key one in this area – choose something very generic and prevalent and, while there may be lot of engineers available in that space, they may be looking to move to newer, more exciting technologies; on the other hand, choose something very niche or “cutting-edge” and you find that the total addressable talent pool is too small to begin with. Getting the balance right is the key to making a good start on this journey.

Working with recruitment partners that know and understand the space, have an active network of candidates and the right infrastructure to help organisations grow can make a big difference especially in the early phases of scaling when an in-house hiring team with the right experience and network might not be in place. The focus needs to be on identifying the right group of diverse and talented people to build the team with – using the right recruitment partners and channels makes a big difference in attracting the candidates in the early stages of growth as marketing plays a key role in building your brand awareness amongst your target candidates. In a fast moving market, it is important to have an ultra-streamlined hiring process as well as to prioritise the delivery of a world-class candidate experience all the way from the initial outreach all the way to their joining. The hiring process gives a great opportunity to understand the core values that the candidate would bring to the organisation – the “cultural fit” is the most important aspect here as knowledge, skills and experience can all be further gained, honed, and added, respectively, after hiring. Quick, decisive, competitive offers go a long way in closing the best candidates and the inputs from recruitment partners who understand the market are vital in this regard too.

If you get all of this right, “Congratulations! You have got an excellent new addition to the team and now begins the next challenge: looking at retaining and growing your new team member”; so they are not only excited about the week ahead every Monday morning, they also find a meaning, a purpose in the work they do that is sustainable, fulfilling and enriching in all respects at the same time.

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