The Biggest Challenges Faced By Start-Up CTOs

There is no definitive consensus on what qualifies as a “scale-up” but the transition from start-up signifies a major shift in the role of a CTO.

Some use financial metrics, others arbitrary milestones but you’ve done it. You’ve shaken the label and connotations of a start-up and are spearheading into the scale-up phase of the business.

There’s a certain expectation of struggle during the formative years but growth can also be scary and brings its own unique set of challenges. Unfortunately, there is no playbook for technical leaders.

The size of the company often dictates the role, and moving away from start-up denotes a step away from a million different daily tasks to shaping the overall technology strategy for the business.

Having helped guide companies through this transitional phase, there are a handful of common problems faced by a scale-up CTO.

Finding The Right People (Now).

Even the most innovative ideas or products will fail without the right people.

The ‘Great Resignation’… ‘Reassessment’… ‘Reshuffle’, whatever we choose to call it, has massively widened the gap between supply and demand of workers.

Some suggest that as we head into the post-pandemic business environment, everything will reset and return to normal. For now, however, HR departments are scrambling to attract talent from a seemingly shrinking pool.

As you transition to a ‘scale up’ you will need new people, either to add additional capabilities or meet more stringent deadlines.

The not-so-easy question of “in-house vs outsourced development” has long troubled start and scale-up tech firms but the answer is clearer than ever.

It is a matter of when not if you will need to rely on outsourcing to get a project unstuck. As a CTO, developing clear objectives for this conundrum is critical.

You may look to hire engineers with core skills aligned with your technology choices. Outsourcing, however, will allow for short-term access to top talent and reduce any delays when you need to move at speed.

Maintaining Alignment Between The Product & Business Goals.

It’s easy to become fixated on the product once funding is raised.

A degree of validation has been received – enough to raise funding – and it’s full steam ahead. As the company grows such laser-focus can lead to a detachment between the product strategy, customer needs and the overall commercial strategy.

In order to avoid any drift, everybody must have a clear understanding of where the company is headed and what metrics must be achieved.

Goals should be up-to-date, completely transparent and visible across all team members. OKRs can be a powerful framework, but ultimately communication and transparency are key.

Assuming continued product market fit can also be dangerous. You are yet to prove complete fit on a larger scale and can lose touch with real customer needs if you become too focused on development.

As CTO, sit in on marketing meetings to ensure the engineering requirements match what customers value.

Security And Governance

The rulebook changes once investors become involved.

What was once flexible becomes more rigid including security. Any investor will want to see a security policy to ensure compliance. Although less of a priority during the start-up phase, registering security procedures step-by-step will avoid a scramble when an audit becomes mandatory.

We have already spoken about the inevitability of outsourcing and copyright law has become a hot topic – “who actually owns what?”

In most countries, whoever writes a piece of code is the proprietary owner and investors will not risk being reliant on knowledge or IP of an external party.

Having proper governance and a transfer of knowledge in place will avoid a monumental headache, large delays and, at worst, a lawsuit further down the road.

Building Quality Into Processes

It’s likely some suboptimal technical decisions have been made during the start up phase. And that’s ok.

Incurring technical debt can be the right thing to do in order to react quickly to transient customer demands. It will, however, need to be properly managed and rectified to enable sustainable growth.

Start with small steps when building quality into your processes. Slowly adopt standards for writing code, increasing test coverage and targeting accessibility benchmarks.

Changes can be manual at first, but over time can be automated to embed quality into everyday processes. This is how an organisation can move towards adopting a DevOps mindset.

On a broader point, be mindful of decisions made now that could become a blocker in the future. A fully agile DevOps organisation should be able to remove the time between problem, ideation and solution.

Speak To A Peer CTO.

The role of a CTO is becoming continually more challenging due to the rapid emergence and application of new technologies. At Digital Village, we have a number of On-Demand CTOs and technology advisors ready to help shape your organisation’s technology decisions.