I interviewed 10 Chief Technology Officers in the Chicago proper area (of different company size, age, and industry) to learn a bit more about the DNA of what makes a CTO successful. Through my research, I noticed a common thread that the average tenure of a CTO is about three years or less, whereas other C Suites’ tenure is far longer. This was very confusing to me because, when 458 CTOs rated their job satisfaction, the average rating was 5 out of 5 (Payscale.com).
The 1st common theme found is that there is a ton of ambiguity around what a CTO does, which makes sense as this is one of the newest C Suite titles. Wikipedia says that “A CTO’s Responsibilities include: Developing the company's strategy for using technological resources. Ensuring technologies are used efficiently, profitably, and securely.” I found that depending on the size, tenure, and industry, each role is fairly different.
The 2nd common theme found relates to the former note - when the company’s technology is working efficiently, profitably, and securely, how does a CTO still show that they are adding value to non-technical stakeholders? Here is their advice.
1. Develop Your Current Team and Share Your Passions
Showing your other C-level peers that you are able to retain your current team is extremely valuable. Let’s be honest, we all have noticed that every company on the planet is always open to hiring developers. One CTO I interviewed had an employee go to a competitor when there wasn’t Diet Coke stocked in the fridge because he/she felt devalued. There are that many jobs open. Developers know that they are a hot commodity. Show them why your company is where they should be.
Bill Kleyman, former CTO of MTM and now Director of Technology Solutions at EPAM Systems (global product development and digital platform engineering services company) says, “Progress comes from the concerted effort of the entire team – emboldened by the direction of the market and the organization.” Bill shares that he’s learned that it’s so much more than just knowing the technology and how to configure a certain service. It’s about connecting with the process, the business, and most importantly, the people.
Chris Doyle, CTO of Ascent (A RegTech firm that helps customers simplify and automate their regulatory compliance programs), expressed the majority of his job is about “building teams and people instead of technology.” He expresses that this is why even though it is hard to find developers these days, it is important to wait and hire good people that you trust and feel confident in to do the work.
Another theme I heard related to development of your team is to share your creative passions. Share with your team so that they will share with you. Andrey Stryukova, The CTO of Countbox (A robotized pop-up store), shared, “I always liked creating things - piano, guitar, DJ’ed on the side, had a weekly radio show.” He found that his team connected with him better when they both shared their passions - work and non-work related. It raised creativity levels on the dev side and helped keep things from getting stale when his team was not able to work on new technology for long periods of time. Find out what your team is excited about.
Anthony Broad-Crawford, CTO/CPO of SpotHero was also always a creator of some sort. From his experience as a professional classical musician to being an architect of many ideas, he continues to share his creative passions with his teams. He is very interested in anything creative that bridges the intersection of design, tech, and business.
Remind your team that they are part of the future and something really exciting. John Higginson, CTO of Enova International (a leading FinTech company headquartered in downtown Chicago) and formerly FTD, mentioned how fascinating it is that “a computer used to be a place you visit, and now, you can take this box, make it do nothing, or make it play music, or teach people.” Remind your team how far the movement they are a part of has come. Even if sometimes it feels like they are doing the same thing over and over again, they are a part of something so much bigger that will continue to evolve and grow. Technology is the future; why wouldn’t they want to be a part of an industry where they will ALWAYS have lots of job opportunity?
2. Continue to Develop Your Networking, People, Leadership, and Blogging Skills
Continue to develop your leadership skills. Although many of the CTOs I spoke with seemed to be very outgoing, not all of them were born naturally outgoing or ever thought they would want to be in a leadership/“People” position. They had to take time to really learn what it meant to be a good leader (and want to be). Andrey from Countbox says, “If you would rather talk to computers than humans, a CTO role is not right for you.” He goes on to say that you will rarely use your programming skills, instead, you will use your people, creativity, and investigative skills.
Brent Laufenberg, CTO of Rise Interactive (a digital marketing agency that specializes in digital media, customer experience, and advanced analytics), says that usually when people leave a CTO role willingly, it is because they don’t want to deal with the “people stuff.” He personally loves to coach and mentor his team members to be better professionals individually, as well as how to work together as a better team collectively. He also loves to explain to people how technology is changing the world for the better and genuinely helps people. He also says that Authenticity and Transparency is everything. Show what all of the teams are working on and be open about how well things are working or not working.
Continue to build your network and stay on top of new technologies. Brent also shares that being a CTO in an organization can feel “information lonely” at times. You need to surround yourself with peers that you can ping new ideas off of, as there is no other C suite that will speak your language. Technology changes every day. It can be very stressful knowing which new technologies to go with, but having a group of peers to share your concerns or perspective with for candid feedback reduces the stress of ‘getting it wrong.’
Dan Rumny, CTO of Ohana Pediatrics (a web-based virtual platform with pediatric-specific workflows, allowing physicians and families to deliver/receive care virtually), says he likes to stay involved by building relationships with tech bootcamps to help finalize people’s career paths and also stay on top of what talent is out there and what salaries should like, as well. This also keeps him up to date with what new technology is out there.
Bill of EPAM says that it is imperative to keep on top of the dynamics of the market and the business. He quotes, “There will not be a stationary moment in technology. So, don’t get too comfortable. Read blogs (or write them!), talk to customers, touch base with industry peers, and have good conversations with your own sales people and engineers. It’s critical to understand which way the industry is shifting. And, very often, you can understand these shifts via the actions of end-users and customers. The role of the CTO is to stay aware of the changes as they happen with partners, competitors, vendors, users, and the overall business.” Networking helps with all of this.
Share your success and failures with your peers. Openly sharing with other CTOs will make you feel less alone and also empower you to make changes yourself. There is a reason why 39% percent of the population watches reality tv (although often not entirely reality, it depicts a version of it) - it shows people that they aren’t alone with the crazy things that can happen in life. Share your stories,failures, and wins with your community. Then share all of these stories with your other C Suite executives.
Bill believes that in order to be a true CTO you have to be inspired by technology and all of the amazing impacts new technology tools have made. From there, he says that you have to inspire others to share this vision and see where new data center, cloud, security, mobility, and IoT tools are truly making a difference.
If you are new to the Chicago Tech Scene, here are some resources for upcoming networking events in Chicago.
3. Learn to be Comfortable with Wearing Multiple Hats, Shifting Hats, and in General, Being Comfortable with Being Uncomfortable.
You need to be a big picture thinker, able to wear multiple hats that change all of the time, be a very quick learner, and be an excellent communicator. “Progress comes from the concerted effort of the entire team – emboldened by the direction of the market and the organization” (Bill, EPAM).
With larger organizations, a common theme I heard was, “I can’t remember the last time I pushed up code.” A trend found from interviews was that in smaller organizations, CTOs were still involved in the coding and QA process. Some CTOs have more ability in the growth process, some are more comfortable with creating a structure of stability (Dan, Ohana Pediatrics).
Chris of Ascent has advice for startups that are starting to see real growth. “You need to be ahead of and aware of growth transitions. When you start at a small startup, and as the company grows, you need to be able to grow and adapt. There is a middle point that will be tough. There will be way too much to do on the IT side and the management side, and you will feel like you are not doing any piece of the job effectively.” He says you will need to learn how to be okay with the fact that you can’t see a tangible contribution (code).
Grant Koeneke, CTO of of Driftr (a social travel app) says that at smaller companies, the CTO can even start as the “sales person” that really has to act as an engineer and architect of the product. He quotes, “Sometimes you are hiring, firing, and then telling people what to do on the architecture side.”
Learn to be comfortable with the uncomfortable – always be ready for change. As a CTO – you are the driver of change. That means you must be aware of new technologies or solutions that are constantly coming out. From there, it’s critical to understand how these new IT systems impact your business, your processes, your users, and the overall market. Finally, you must always be ready for change and to help guide your organization (and your customers) through the IT evolution process” (Bill, EPAM).
The biggest trend that Gulé Sheikh ,COO/CTO of eazyScripts (ePrescribing Software for clinics, telemedicine, and hospital systems), sees with CTOs not working out is that they are unable to adapt to the era that we are living in now. Cultural fit is a bigger issue than ever. Be efficient, be able to grow quickly, be adaptable to change, keep up with what is current. She says that you need to be an excellent problem solver and also able to get the right people in the room when needed to help you solve the problem.
Gulé also says a good way to ensure that “everything works” consistently is to project your issues very early on. She builds strategy based on their financial and sales pipeline and the growth they plan for a year paired with the latest technology that will help them move faster. “You need to think as far ahead as you can, and then communicate it to your board, team, and stakeholders.”
What new technologies are CTOs excited about? Almost every CTO that I spoke with is excited about AI and advances in cybersecurity. Other common themes were around how technology is shaping the real estate market, the fitness industry, and car rental/subscription industry. A few CTOs are excited to continue to ride the rollercoaster that is blockchain and cryptocurrency.
4. Learn How to Communicate Process and Value to Non-Technical Stakeholders
A key aspect to technical leadership is being able to take a very technical issue and make it easy for non-technical stakeholders to understand. Chris Weilemann, CTO of CloudSight (A global leader in image capturing and understanding in the AI space), shares his experience. He says, “I've found one of the best ways to communicate value to non-technical stakeholders is through examples or raw data, such as cost savings on a budget or performance metrics in third party analytics tools. The old adage ‘a picture is worth a thousand words’ holds especially true when it comes to more complex topics - it's almost always easier to illustrate a topic of discussion than to try to explain it verbally or in writing.”
Gulé of eazyScripts, says that it is all about how she “lays things out.” She sticks to data and charts. “This is factual and everyone can see how upward trends are positive. I then add my own input on how we got there and the work the team was doing in order to accomplish this.” She says that she will also discuss some of the dilemmas caused by factors that were out of her direct control, as it gives a lay of the land on how the team worked through issues and was able to rise above them.
Gulé aligns herself with the growth of the company in terms of financials. She focuses directly on the areas of technology that will directly impact the growth of the company (or hinder it). She sticks to data and also builds KPIs, so that they can review past performance. In her current role, this is the usage of the software and why they have up-trends and down-trends and the technical factors that contribute to that.
John of Enova says to always stay on top of where the tech of the company is going. He quotes, “It is less about how an application is written, but more what things like Alexa mean to the consumer business.” He says that the CTO will serve as the integration point between the business and technology. Example - come to them saying, “Here are the three ways that we could use blockchain to evolve the business.”
Chris from CloudSight says that when communicating to non-technical stakeholders, show the CEO what is happening or what the plan is through charts, graphs, forecasted metrics, etc. "If we create this service, we'll save this much money," or "if we switch to this infrastructure, our latency will drop by this percentage," etc.
Mike Tai, CTO of EVENTup (one of the largest online marketplaces for event spaces), expresses that it is challenging to convey technical debt/operation changes. He says, “For example - as the business doesn’t necessarily get new functionality - but if you put it in terms that will say….10% investment in time to address technical debut/operation changes, you save 20% in the development capacity.”
5. Promote the Value of Technology to Non-Tech Focused Divisions of the Company, and Help Them Understand Growth Patterns
SHOW how technology helps each sector of the business for a unified goal. Grant from Driftr says, “Get everyone that is non-technical to understand that everything in the company made of technology adds value, whether they have thought about it or not. Example - finance wouldn’t be able to run with three accountants using a pencil, paper, and the US Mail. But, with a finance software system in place and email, you can run with just three accountants.”
He also says “Typically, the non-technical departments take for granted the technology they use everyday to do more faster and more efficiently. Yet, all of these are supported and maintained by a company’s one technology department. To anyone not technical, the way to show them is to turn the software into a monetary value against a department without that software and support. Example - finance with software runs with three accountants at a cost of $XXX versus 12 accountants at a cost of $YYY. Of course, this is really basic. Usually it would be quite detailed.”
Constant clear communication – with everyone - is imperative. Bill of EPAM says that he can’t stress this enough. “I regularly chat with our amazing sales teams, engineers, architects, inside sales, procurement, support, HR, and many others.” Clear communication means discussing objectives and strategies with one individual who might be curious or leading an entire session or webinar on the direction of the company.
Chris from CloudSight says, “It’s easy as the CTO to be technical. That’s our bread and butter, but getting involved with the business side of the company, whether it be operations, sales, marketing, or other areas, will be equally important."
Gulé of eazyScripts also had a very interesting point around expectations of growth with a startup and how to express them to your other team members. "Everyone thinks that when you are startup, things should move quickly because there are less people to approve things, less divisions, less legal. The reality is that when you are small, you have multiple people doing multiple big things. It takes time to get each thing done and just as quickly, tech is always changing... With larger companies you have a ton of people doing really small jobs, so you can move way quicker. You also don't deal with the mental burnout from doing all the jobs at a smaller company, you don't hear about the 10 years it took for a startup to even figure out what their niche is, you just see this cool new app like .. poof."
Mike of EventUp really resonated with the question, “What to do when everything is working.” Mike says, “There are situations where a CTO role has openings because there is a problem to be solved.” A CTO must think beyond that problem. For example, “we need a CTO for a specific project.” Once you are only doing support on this project, you need to find a new initiative to start working on while you are supporting the thing that you just finished.
Mike also says, “It is your job to help determine and express the ROI of business initiatives. This also means getting involved in product planning and business strategy alignment and coming up with new solutions that did not previously exist.”
Hope this helps!