Advice From Those Who Have Made It: A CTO’s Guide for Graduates to Become One

• The United States has more than 557,000 technology companies that support 12.1 million jobs.
• The technology sector contributes more than 10% ($1.9 trillion) to the annual U.S. GDP.
• With such an expansive industry, how can an aspiring techie navigate through the myriad of options on their path to the top tech job: the CTO?

A chief technology officer (CTO) overseeing an organization’s tech strategy is an exceptionally important role in the modern-day business environment. Technology can make or break a company operationally and financially as it enables communication, collaboration, customer experience, and more.

Technology-enabled businesses also usually enjoy an expansive total addressable market, provided they have the right infrastructure. A CTO is thus responsible for enabling a business to achieve its goals by developing, implementing and managing the technology infrastructure and hiring and managing the right people.

Not only does the CTO job entail knowledge of the relevance of varied technologies, but the C-suite role also necessitates strategic technical planning and leadership qualities alongside a knack for financial planning.

What Does a CTO Do?

A CTO executes various broad-stroke aspects across the technical board. These include but aren’t limited to the following:

• Create a roadmap for tech stack implementation
• Manage said tech implementation through the technical team
• Keep track of technology advancements and facilitate upgrades
• Design and enforce technology policies
• Manage budgets
• Coordinate with cybersecurity and other departments
• Relay technology policies and approaches within the organization

We asked Chris Hill, SVP and CTO at Spiceworks Ziff Davis (SWZD), what the role entails. He noted that it is highly organization-specific. The CTO role overlaps with multiple functional areas within the organization, including revenue drivers, such as software development and engineering, and strategic functions by delegating medium and low-level responsibilities to a set of leaders.

Hill also emphasized how cybersecurity is now one of the most important functions of an organization. “Today, with the much heightened need to focus on security, a CTO’s focus on security is typically more of a given now than in the past,” Hill said. “In today’s world, Security is everyone’s job, but people have to be lead through those disciplines with standards and processes.” He highlighted how a chief information officer (CIO) sometimes has similar responsibilities.

Chris HillOpens a new window , SVP & CTO, Spiceworks Ziff DavisOpens a new window

Hill encapsulates the CTO role with the following diagram:

The CTO Role

“Every company has different needs, and every instance of a CTO role is different. I tend to stay more in the middle of the triangle, because I like to remain close to software engineering. You will find that the larger the company, the more likely that the CTO will have more pressure pushing them to the top of the triangle, staying more focused on strategic planning, leaning on their organization to do the majority of the low level work. I find that the organization and its style of operating will almost organically dictate the plotting of where their CTO needs to be in the triangle. Finding the CTO candidate who’s comfortable and able to execute in that spot is the tricky part, largely because many CEOs doing the hiring for a CTO don’t understand the three core dimensions of a CTO and what is really needed by their CTO to enable success in their organization. I think the best CTOs are flexible and can operate anywhere in the triangle.” – Chris Hill, SVP and CTO at Spiceworks Ziff Davis

Why is the CTO role Attractive?

Hill believes that everyone has different motivations. Whether it is a technology role model they aspire to emulate, financial incentives, or hope to lead a team one day, the CTO job can enable them to achieve this all.

“To have a big team and a lot of scope in your job seems exciting to some. Almost every developer I ever had on a team in my career aspired to have ‘people’ – to be a manager. Sure, some developers just wanted to write code and not have to worry about the hassle of dealing with people issues. But those that are the true leaders find their path to growing scope with respect to people leadership,” Hill opined.

“A CTO is no more important than any other senior leadership role in any other industry. Managing the technology to ensure smooth operation of the company’s products and ensuring that there is harmony in the technical team, takes a lot of focus, people skills, patience, technical knowledge and the know how to use all of these skills to keep the team functioning properly.”

How to Set Yourself on a Path to Become a CTO

According to the U.S. Bureau of Labor Statistics (BLS), a person must have at least 15 years of experience in the technology field before being considered for the CTO position. Meanwhile, most CTOs started as engineers in the field.

However, techies must inculcate the necessary managerial skills, preferably five to seven years, in the field.

Hill began his interest in technology by “taking things apart and seeing what made them tick.” By that, he meant building and repairing personal computers. His inclination towards hardware was complemented by learning the logical aspects of the underlying software. This included writing database applications with COBOL on a mainframe and a few 4GL programming languages.

After years in technical roles, Hill worked in senior leadership roles at IBM’s The Weather Company for 17 years before moving on to IBM as VP and chief information and technology officer for five years. He has been the SWZD SVP and CTO for almost two years.

Here’s what Hill has to say to fresh graduates out of college:

Participate in as many projects as you can

Work in highly technical roles before climbing the proverbial ladder within the organization to emerge as a technology leader. “CTOs are leaders, and leadership is not a spectator sport,” Hill writes. “I think the best CTOs are ones that came up through an organization and learned about technology, hands-on. If you have never been a developer or worked deeply in technology, it is hard to lead it effectively. Impossible, no, but I always had much better relationships with my leaders  below me when they came from where I was.”

The process is incremental, and one of the building blocks to successfully becoming a CTO is putting yourself out there in leadership roles, initially starting small and then taking on bigger challenges.

“Two things will happen. You will decide that you hate that and want to be an individual contributor, or, you end up loving it, maybe excelling after possibly some stumbling blocks, and the next thing your personal brand is now associated with leadership. Keep doing that, until you grow your scope,” Hill said.

“Don’t be afraid to take chances and change jobs to get those newer, and larger, leadership experiences. Most of the significant jumps I have made in my career happened when opportunities arose, and was asked ‘who can do this.’  I always raised my hand.”

Advanced degrees and certifications

Degrees and certifications can help aspirants to jumpstart their careers, but it’s the experience in those early technical roles and leadership positions that truly pave the way to eligibility as a CTO. 

“Some of the strongest leaders and technical minds I know either didn’t go to college or did not major in a technology or science programs. The first thing is that you don’t graduate college to be a CTO, you graduate to start your career which may lead to that, after a lot of hard work and experience gathering,” Hill explained.

Still, a bachelor’s degree is desirable, followed by an early master’s programme. “Getting an MBA, perhaps later in your career, is a great way to learn more about the business side of things, which CTO’s most certainly need to learn.”

However, the possibility of IT pros’ inclination to head back to school for education after years in the industry may be non-existent, like Hill. This is why he learned at the job, something he doesn’t recommend.

“Degrees and learning are great, and big rewards can come from that – but, experience is more important in my opinion. They are not mutually exclusive. You need an opportunity with which you can practice what you learn, with some recency to the learning. That is not to say that you forget everything you gain through degrees, but ask a computer science graduate, 10 years later to solve a linear algebra problem – most cant. Learn it and use it.” – Chris Hill, SVP and CTO at SWZD

When learning anything new via certifications, Hill advises focusing on technologies relevant to the job/industry. For instance, a developer working in a company offering microservices may find it helpful to learn API development. Hill says this allows them to put the new skill to work immediately.

“I am not a huge fan of technical certifications, but I am not against them either. There are many certifications that are relevant to many different technologies. Learning is rarely a bad thing,” Hill added. “Otherwise, the new knowledge will dissipate and not be nearly as valuable as if it was put into practice right away.”

This also opens up aspirants to becoming experts in the industry, which will help them emerge as technical leaders in the future, better positioned to build products aligned with the company’s mission and values.

Skill development

Hard skills are necessary because they are the basis on which prospective employers gauge the eligibility of CTO candidates. Hard skills include real-world-applicable systems analysis, data analysis, programming, database management, cloud-based development, and, more recently, artificial intelligence and machine learning.

Hard skills can be learned in college and acquired and refined over time through professional experience. On the other hand, soft skills may not be a prerequisite for being eligible for the CTO role, but they are necessary for smooth functional teams.

“I didn’t coin this phrase, but I always say that technology is easy, people are hard,” Hill added. To gain their trust, you need communication skills and the ability to build strong relationships to gain their trust. Hill describes how Situational Leadership has helped in this regard, whether dealing with those he has led or those he has reported to.

Communication skills and executive presence come in handy when delegating decision-making to others, as it is important for them to understand what the team is doing and why. “When things stray off track, the CTO must reinforce the points to get everything back on track. Sometimes people leadership at scale is really hard. Making decisions that people don’t agree with, having to deliver messages that are unpopular but out of your control, or even the simplest of problems dealing with personality conflicts and grievances. It’s hard at times!”

“It is a cliché to say that a CTO is like the conductor in an orchestra, but they are the person that has the ultimate responsibility for the technology, and thus being accountable to the CEO for all of it, so they don’t have to worry about it.” – Chris Hill, SVP and CTO at SWZD

Industry knowledge

Technical knowledge is great, although industry knowledge is a key aspect of successfully navigating the road to emerging as a senior technology leader, such as a CTO.

“As your career evolves, and you traverse through multiple industries, I find that it is really best to learn that industry inside and out.  As a technology leader, or even an individual contributor, I feel like you have a much better chance to be successful if you understand the industry and context in which your products will be used,” Hill continued.

In this regard, the company’s reliance on non-technical personnel can help a lot in understanding the context of the industry the company operates in. 

“Understanding the general personas of the people who exist as customers in your industry, and even more detailed understanding of the even more targeted personas who are your company’s direct customers, only makes you more informed and able to lead teams to build the right products for the right people.”

MORE ON IT CAREERS

• The CDO’s Survival Guide: Navigating the Data-Driven Minefield
• Tech Success Without Degrees: Hiring for Skills
• The Impact of Digital Adoption Platforms on Organizational Change
• Talent Upskilling and the Cloud: The Pillar for Company Growth
• IDPs Help Organizations Hire the Best Developers — and Ensure They Stick Around