The Google Sheet mentioned in this article is available to anyone here.
If you don’t work in tech (and perhaps even if you do), you may not know that the ‘ultimate’ tech role in a company is deeply varied. The same role can even change over time in the same business, and this means that CTOs either need to adapt or be changed to suit the needs of the business.
I spend much of my time helping companies understand what type of CTO they need. I’m also fortunate that I am able to ask the same question of CTOs (and aspiring CTOs), asking what type of tech leader they want to be. Sometimes this leads to a discussion of whether the CTO role is really right for them. In many cases the broad responsibility and lack of hands-on focus asks them to leave too many of the things they love at the door of the office.
The Swiss Army CTO
I entered the tech world back in 1997 with no formal training in technology. I left university with a social science degree which had the significant benefit of allowing me to spend a great deal of time in the university computer centre waiting for one of my four lectures a week. That spare time meant that I sat and hacked together websites, at a time before Javascript even existed. Hacking websites got me my first tech role, which has provided me a wonderful career in technology.
Being a kludgy hacker, and left with little oversight, I picked up every tech role possible. I administered databases, bought hardware, put kit in datacentres, scaled infrastructure, built engineering teams, designed product roadmaps, moved to the cloud and took on the world of corporate IT, rolling out CRMs and desktop support. My career is just the top of the ideal T-shape; I know a lot of things, badly.
The Corporate CTO
Growing up as a tech leader through the noughties mean that I got to hang out with a lot of ‘IT’ folk. The conferences that I attended were studded with unhealthy looking white males of a certain age, primarily from large corporations. Their CTO roles were defined by million dollar projects with hundreds of staff, their seniority conferred upon them by the size of their support teams and the number of digits in their budgets. Size mattered. The monstrous corporates — IBM, HP, Oracle, Microsoft — dominated their conversations, and their role was at least half accountant; they spent their time negotiating million dollar licence deals, understanding the best way to capitalise massive hardware purchases. Playing golf was a requirement of the role. Back then, it was common for CTOs to report to the CFO, who had traditionally owned the only tech in the business, the finance system.
The Startup CTO
But slowly, as the noughties gave way into the teens, the CTO role changed. Technology was no longer massive corporate systems, marked by the number of desktops being managed. Suddenly tech became software engineering, and tech leaders were firebrand coders. Grey, corporate suits turned into hoodies and trainers, and the tech leadership role became one of software delivery rather than hardware procurement. In many cases, the CTO had to balance both an engineering background and a product responsibility. Increasingly, the CTO role came to drive company strategy with the product backlog sitting front and centre as the company’s unique strategic position. This generation of CTO, especially in younger companies, often had no experience in ‘business technology’ — the boring stuff like providing phones, or CRMs, or HR systems.
The awful choice for startup CTOs
One of the things that I’m now commonly asked to help companies with is moving from scrappy startup to scale. At somewhere near the fifty people mark, startups start to experience scaling problems. The loose groups of tech, sales, product and leadership start to strain, and problems of omission and oversight occur. GDPR happens. Meetings with investors demand financial forecasts. Onboarding new starters into the business is more frequent. Laptops need to be bought. More people leave, and user accounts are left hanging open. The tech team starts to scale, and finding talented developers becomes a problem. One engineering team becomes two squads, and cross-team communications starts to falter.. With each additional head, the requirement for greater specialisation in tech skills is in tension with the ever broadening scope of the CTO role.
Often in this situation, eyes fall on the ‘founder CTO’ to pick up any problem with a plug attached. The once brilliant engineer, responsible for the early success of the business and renowned for superhuman effort, is dragged further and further from her first love — building software to solve problems.
And here’s the awful choice for the tech leader to face — do you want to scale with the business, or do you want to do what you love? Noam Wasserman’s Founder’s Dilemma exists just as strongly for technical founders as it does for their visionary partners.
The CTO archetypes
Over the last few years, I’ve been tracking the type of skills that businesses require from their CTO, and I’ve created a high level set of skill groups that can help businesses understand what type of CTO they need at these inflection points. Perhaps more usefully, it can also help CTOs decide what they want to be when they grow up.
While the scales will vary for each company, here are common high level capabilities required by different CTO roles. You can imagine that there will be a set of sub-scales under each of these scales.
Domain Knowledge
How important is it that the CTO has worked in this domain previously? Is there some highly specific knowledge required that would take too long for someone without this experience to gain. In some fields, such as healthcare, GIS or finance, domain knowledge can be crucial to the role. In others, domain knowledge can be gained along the way, and often more quickly than people realise.
Engineering
Is this CTO role primarily working to produce software or platforms? Is the CTO capable of working with complex software development principles and teams? Does the CTO need to make hands on decisions about code and infrastructure? In some companies this is the majority of the role, in others (for instance many SMEs), there’s no requirement for code at all.
Strategy
Will the CTO be required to drive the company strategy? Will they be interfacing at board/C-Suite level, or with investors to construct and communicate an overarching strategy. Is the company planning more than a year out, requiring a sound knowledge of strategic management principles?
Product
In many tech businesses, product and technology go hand in hand. Often, the CTO and Chief Product Officer (CPO) role is conflated. Does the CTO understand how to build new products and maintain existing ones, rather than just build the code to support them? Is there a CPO, or strong product group already in the business?
Business Technology
Does the CTO need to take responsibility for end user technology? In some businesses, this can be the majority of the CTO role, for instance supporting international teams with complex phone systems, CRM, email, ERP and even domain specific technology like manufacturing or stock control systems. Is this already handled in the business by another role, perhaps a CIO or COO?
Data
Is there a specific requirement for the CTO to optimise and manage organisational data? This is particularly true for large, highly transactional systems, or businesses that have complex data requirements like data science teams or a need for data warehousing or complex BI systems. In some companies, data is the lifeblood of the business, in others it’s an addendum.
Large Teams
People management is an entirely separate skill from large engineering challenges. Has the CTO worked with large, complex teams. Do they have a good understanding of performance management, objective setting, culture and recruitment, that is needed to build and maintain teams? Is the role well supported by a strong HR/People function in the business? Is there likely to be a requirement that the CTO will need to perform difficult or complex HR activities, like firing poor performers, making redundancies or offshoring a large team?
Commercial
With scale comes commercial complexity. Does the CTO have the ability to create complex financial models to work within the business. For instance, do they need to be experienced with capex and opex tradeoffs, do they need experience of mergers and acquisitions or difficult procurement processes?
Security & Compliance
There is a baseline for all CTOs to meet with security and compliance, but in the context of the business, is there a higher bar to meet? For instance in the healthcare, financial or legal sectors, security and compliance take a much higher priority. Enterprise risk and standards like GDPR, HIPAA, ISO27001, SOC2/3, PCI DSS and the CCA CSM are painful but valuable. Will this role need a special focus on these?
The modelling problem
This model is naturally a simplification of the CTO role, and there’s a balance between complexity and ease of use. In many businesses, the model can be broken down into a simple binary question; “Is this an engineering CTO or a Business Tech CTO?”. For tech businesses, it’s usually the former and the challenge is code or infrastructure. In other SMEs, their struggle is with buying the right systems and supporting end users.
The unicorn CTO
The key point to be aware of is that these are not exclusive scales — being a great engineer doesn’t prevent you also being great at product strategy. However, you should assume that the more ‘world class’ capabilities that one CTO demonstrates, the more they are worth to the market. You should assume that you’ll pay dearly for the privilege of hiring one of these 9-point unicorns.
There is also the challenge of headspace. This is something I experienced painfully in my career, growing with a company to take responsibility for everything from UX Design to Data Science, with business tech in between. The context switching between so many disparate and disconnected projects and domains was painful. The option that I took was to restructure my role, splitting it into two, with Product and Engineering in one role and Business Tech and Operations in another. It was obvious that I was doing a bad job trying to manage all of this in one house.
Scoring yourself
Out of interest, here’s my self scored, swiss-army knife CTO persona — I’m passable at data and engineering, but I love working on Strategy. I’m capable at both Product and Business tech; if you want me to write code, I’m definitely the wrong CTO for you. If you want me to roll out Office 365 or Salesforce, no problem.
In this example, I’ve left out Domain Knowledge. If I was asked to work inside a recruitment business I’d score pretty well (but never again, thanks). If you wanted me to join a widget manufacturing firm, I’d need some time to get up to speed on your widgets. Your scores, like mine, will always be contextual.
The Google sheet is available to anyone here. Please feel free to make a copy and play with your own scores — I’ve left mine in as an indicator for you.
Please also feel free to join the conversation and add to the discussion of what makes a good CTO. What have I missed out? What could I leave out?
I’d also love to know how you, as a CTO, or as a business score. What does your perfect CTO role look like?
